my employee dresses like a slob

A reader writes:

We have a generally business casual office. I have a direct report who just dresses sloppily. He is by the book following the dress code, but he kind of looks like he just rolled out of bed. He is clean, but looks messy. He will wear a polo or henley shirt, but rarely tucked in. Often his pant hems are frayed. He wears shoes that are the ambiguous type that are sneakers but meant to pass as shoes. The clothes are baggy.

We work in IT so none of the techs care too much about looking fashionable, but pull off a reasonably professional look with a simple polo and khakis and belt. This person’s role is supposed to be more forward facing and collaborative with others across the organization, not just sitting in a room coding.

I am also concerned that, depending on how I approach this, he will tell me that X is wearing the same thing as he is. However, X looks put together, not like he rolled out of a hammock in his office. I think that this guy would rather be sequestered in his office or work from home, but that is not the reality of the job right now. He is hurting his prospects with the organization as a whole because my boss views this even more negatively than I do.

I don’t want to offend my employee, who does do good work. Any suggestions on how to discuss this and get the point across to someone who seems clueless about clothing?

I used to work with a guy who we affectionately called “the unmade bed” because he was sloppy in a similar way. It was fine in his case – his work didn’t require him to look particularly polished. But in your employee’s case, it sounds like there’s an actual work reason for him to look more pulled together.

I wonder, though, if you can narrow the scope of the issue and hone in on one or two changes that would make the biggest difference. For example, if he tucked in his shirt and lost the sneakers, it might not matter so much that his clothes are loose and his pant hems are frayed. If that’s the case, this gets easier to address. You can just say in a matter-of-fact way, “Hey, you’re pushing the dress code a bit – would you keep your shirts tucked in while you’re at work and swap out those sneakers for less casual shoes?”

But if that won’t do it, then just be as straightforward as possible with him. People tend to agonize over conversations about dress and grooming because it feels so personal, but the more you keep in mind that it’s not about him as a person or a condemnation of his personal style choices, the easier it will be. The way he dresses is fine for his life; it’s just not appropriate for this job. That matters because if you go into the conversation thinking “ugh, you’re such a slob,” it’s likely to come out in the framing and tone you use. But if you go in thinking “I want this guy to be noticed for his work rather than his frayed pants,” you’re more likely to sound like you’re on his side, which will give you both a better shot at an easy resolution.

It’ll also help to look at this like any other feedback conversation where you talk to him about something that you’d like to see change in his work – “here’s the issue, here’s what I need you to do differently to solve it.” For example, you could say: “Because your position works with so many other areas of the organization, it’s important that you look put together. When you leave your shirt untucked and wear sneakers and loose-fitting or wrinkled clothes, it doesn’t look pulled together enough for the visibility you have in this role. You don’t need to wear a suit; I’m just talking about fairly small tweaks.”

If you frame it that way, he shouldn’t be able to retort that a coworker is wearing the same thing. But if he does, you can simply explain whatever the difference is – that Bob’s shirts aren’t wrinkled, or they’re always neatly tucked in, or whatever the explanation is. And if relevant, you can also repeat that it’s his outward-facing role that makes the standards particularly relevant.

If he says that it’s unfair that he’s being judged on something other than his actual work, you can agree: “It is unfair. But the reality is that it will affect your credibility and I don’t want to see it take the focus off your work, which is excellent.”

Originally published at New York Magazine.

{ 338 comments… read them below }

  1. LQ*

    I like so much the direct, it isn’t fair and that’s the way it is phrasing. I will definitely be tucking that away.

    1. Ask a Manager* Post author

      Sometimes I think managers get caught up in trying to defend this stuff, when sometimes it’s really okay (and more effective) to agree that it’s not fair but is how these things work. (Although it doesn’t always work — you don’t want to say it if it sounds like you’re trashing the company culture or something like that.)

  2. Roscoe*

    This is a tough one, because a lot of it does come down to personal opinion. I know I don’t necessarily find much of a different between a tucked in polo and untucked polo. Similarly, there are some shoes that really could go either way, which his sounds like they are. So while I get what you are saying, some of it really does seem like you passing a bit of judgment based on your preferences, not that he is really breaking the dress code.

    But if you are definitely going to have this talk as Alison said, you really need to put the focus on the WHY of it and keep your personal judgments out of it. Because again, as you say, he isn’t breaking the dress code, just not as put together as you’d like. So if you can explain that he needs to look more presentable because he is working with outside clients or whatever, it will come off better.

    1. Megs*

      I think that’s part of the OP’s problem, though – no single thing the employee is doing is breaking the dress code, but they’re toeing the line in so many places at once that it’s causing a bad impression with the higher ups. Under those circumstances, I think it’s absolutely appropriate to at least have one talk with him about it. If he decides that he’s going to keep doing what he’s doing because *technically* he’s not breaking the dress code and to heck with upper management, that’s up to him.

    2. Karo*

      I see what you’re saying with your first part but there’s a huge difference between three mussed/fraying/borderline pieces of clothing and 1 borderline piece with everything else great, you know? So, if he is wearing crisp khakis with a nice shirt, tucked in, and borderline shoes, fine. But fraying pants with questionable shoes and and a mussed/untucked shirt – all of it combines to be not okay.

        1. Sadsack*

          Also, frayed pants is really pushing it, no matter what kind pants they are. That should be addressed, if nothing else.

          1. Not the Droid You are Looking For*

            Learning to hem my own pants was the best thing ever!

            Too often I had pants that were frayed because I was too lazy to take them to the tailor and too impatient to not wear them. Soooo many ruined pairs of jeans.

      1. Artemesia*

        good shoes, crisp well fit khakis and a clean well fitting polo that is not tucked in is a perfectly good look too and better for most middle aged figures. It is obviously the rumbled ill fitting, worn out mess all together that makes this guy come across so badly.

    3. Not the Droid You are Looking For*

      I think this is one of those situations where the difference is between breaking the letter and the spirit of the dress code.

      I had a coworker who was similar to the employee in question, she followed all the rules of the dress code, but somehow always managed to miss the spirit of it (looking presentable to clients). It was always interesting to me, because it wasn’t a question of not being able to afford things, as she would buy things she knew would press our boss’s buttons, but were technically allowed; but more seemed to be her form of passive resistance.

        1. Not So NewReader*

          LOL. I met a lawyer one time whose shirt was the most wrinkly shirt I have ever seen in m life. He did not sleep in it one night, he slept in it THREE nights. Or so it seemed. This was not, “oh I worked all morning with my sleeves rolled up”. The front and back of the shirt were a disaster.
          I was asked what I thought of the guy. I said “Why has he been sleeping in his work clothes for the last three nights? Something is very, very off here.”

          The lawyer bungled the case so badly it never even got to a judge.

          People do make judgement calls about others, while it’s not always fair, it still happens. I picked up on the Wrinkly-est Shirt in the World and wondered about this guy’s ability to pay attention to what he was doing. If the problem had been only half as bad as it was, I would not have paid attention. He would have been with in range of others in his group, maybe on the edge of his peer group but it would have been easy to figure he was having a long day. OP, it would be an act of kindness to explain that it is a good idea to not make one’s appearance too different from what the group is doing.

      1. irritable vowel*

        I once heard a story on the radio about students at a girls’ boarding school, and a graduate of the school was quoted as saying that they strove to be as much out of uniform as possible while still technically being in uniform.

        1. C Average*

          When I was on a work assignment in Japan, I loved riding the train through Harajuku and observing all the ways that the schoolgirls found to be dressed in uniform but also to look completely unique. It was like one of those “100 ways to wear a basic black dress” that you see in women’s magazines.

        2. Phyllis B*

          Yep. I went a Catholic girls’ boarding school for a couple of years, and while we were allowed to wear shorts/pants during non-school hours, the rule was we had to wear a skirt in the dining hall. A lot of the girls would wear skirt over their pants. The nuns grudgingly let them get away with it because technically they were following the rules. This is also the group of nuns who required we wear nylons to Sunday Mass, and if they weren’t sure you were wearing them, would rub their hands down your legs to check!!

        3. Isabel C.*

          Hee! My mom used to tell stories of girls in Catholic school (not her, of course) wearing the skirts at the appropriate length for the uniform check and then rolling them up at the waist as soon as the nuns stopped looking.

        4. Liana*

          I went to Catholic school for 9 years and this is definitely a thing. We got pretty creative when it came to pushing boundaries of the uniform!

      2. mander*

        Years ago I worked with someone who did this. The company introduced a new dress code which included things like no open toed shoes, no jeans, and no logos, yet my co-worker would get away with wearing white athletic socks with Birkenstocks, a threadbare sweatshirt with kittens printed on it, and one of those drop-waist chambray prairie skirts (because it wasn’t jeans, but a skirt, I guess?). Meanwhile our very stylish *manager* was reprimanded after turning up in a sharp suit with peep-toe heels.

    4. Florida*

      I don’t think it is so much the untucked polo or the casual shoes or the lack of a belt. It is the combination of all of it. If it was one thing, it might be acceptable. It’s the combination of it makes him look like an “unmade bed” (I love that phrase).

      When OP has this talk, it might help to think of work dress as a uniform. If you worked at a place that a true uniform, like a grocery store, then it’s easier to talk to employees about their dress. “Our uniform look is black pants, and you are coming to work with red pants. Please adjust your wardrobe accordingly.” Really, all workplaces have a uniform of sorts. It sounds like OP’s uniform is business casual. So it’s the same concept, “The uniform look of XYZ Company is business casual, not frumpy casual.” That is no reflection on Employee’s personal style. It’s a reflection on the uniform we wear at XYZ. It might help to think of it that way. Good luck.

      1. Joan Callamezzo*

        When I first started in this office, one of my colleagues in a supervisor-level position used to come to work in giant untucked shirts (not a fashionable tunic, just a shirt that looked 3 sizes too big for her), tight leggings, old ratty sneakers, and unbrushed hair. Now our office is business casual, but at the time it most definitely was not. My manager told me she was walking behind 2 women from another department and they all passed Unmade Bed Supervisor in the hallway. When she was out of earshot, one woman murmured to the other, “Oh, honey,” and they both laughed.

        She wasn’t especially brilliant at the job, but she wasn’t terrible at it either. Unfortunately, the first–and lasting–impression people had of her was that she was a slob, and it definitely affected her professional reputation in the office. She left within a year. After hearing this, I resolved never to be the “oh, honey” in that story.

        1. Julia*

          That’s not even business casual, that’s… not even casual anymore. It’s just sloppy.

    5. INTP*

      I agree that none of these is necessarily a problem individually – and the OP acknowledges that he isn’t breaking the letter of the dress code – but all together, they would give a slobby appearance according to general office norms, not just the OP’s personal tastes. You can get away with an untucked shirt or athletic-disguised-as-dress shoe if the rest of your outfit looks perfectly polished, so those things don’t need to be against dress code for everyone, but it sounds like this guy is pushing it to the limit on everything.

    6. annonymouse*

      It is less to do with personal opinion and more how he appears to other departments and clients.

      If say he had crisp khaki pants, tucked in shirt and borderline shoes – fine.
      Untcked shirt, borderline shoes and nice pants – I’d allow it but might mention something
      But frayed (Never a good look in a client job) pants, untucked/wrinkled shirt and borderline shoes – that’s three elements at once not up to standard.

      And again because this person works across departments and with clients it makes him and his department look bad (look what fergus’s boss lets him wear. So unkempt.)

      That’s the reality

    7. Vicki*

      I never tuck my shirts. If I tuck, I look fat, I feel fat, then I feel depressed, then my work suffers. So, untucked polos for me.

      Do people really care about tucked or untucked??? (I’ve had crazy managers but never one who cared about my shirts.)

  3. Bulbosaur*

    I wish tucked-in shirts never became a thing. I hate how shirts looked when they’re tucked in.

      1. Anxa*

        There’s something about tucking my shirt into my pants that just skeeves me out.

        Also, I’ve worked quite a few jobs where the uniform was a tucked in shirt, but the shirts were always pretty long. There was a lot of bunched up fabric in my pants and it just wasn’t comfortable. And then without fail it comes untucked in some places, flashing part of love handle area or small of my back.

        1. Unegen*

          Go look up a YouTube or Instructables tutorial for “military tuck.” It’s a way of tucking in one’s shirt so that the excess fabric is folded in and tidy, and it doesn’t come untucked easily. A real sanity saver.

      2. Bulbosaur*

        I feel like only the very thin can pull it off. If you’ve got any sort of lower belly pooch, it ends up making you look bigger than you are. You either have to tuck in just the very edge of a slightly too-big shirt so you have enough fabric to puff out over the pooch (which makes you look like you have a spare tire), or you have a shirt that is closer-fitting and then puts the pooch on display below your pant waistline.

        1. Manders*

          It works to hide the pooch only if you have very high-waisted pants or a high-waisted skirt, so that the shirt’s tucked in where your body is thinnest. I doubt they make high-waisted khakis, and it would like pretty ridiculous if they did.

          I also think the polo shirt tucked into khakis look is weird, and far less of a problem than frayed or otherwise damaged clothing.

          1. Bulbosaur*

            But then the pooch is sticking out where you zip up your pants. High-waisted would just make it worse.
            As an overweight person, I feel like tucking in shirts makes me look sloppy. If I don’t have to tuck, I can find a shirt of the right cut and length to hit at just the right place to camoflauge the pooch/overhang bulge. If I have to tuck in, then I just look like I don’t know how to dress for my body type.

            1. Kay J*

              Yeah, as a fat person I look waaaay worse in tucked shirts than untucked. It was so sloppy looking when my grocery store job made me wear a tucked t-shirt.

          2. Michelenyc*

            Polo shirts are not meant to be tucked in that is why we add contrast taping to the vents on the side. Everyone needs a little splash of color.

          3. many bells down*

            Yeah I have a long torso AND a mom-belly, so most “normal” rise pants go under the pooch and it looks awful with a tucked-in shirt. I only ever tuck in with something high enough to hit at least my navel.

            I do have some high-waisted shapewear panties and I discovered that they also help a lot with back support as well as taming the pooch, so I’ll wear those to work sometimes just for that!

        2. AW*

          Agreed and body shape matters too. Unless you your waist actually goes in (as opposed to out or even just straight) tucking tends to look bad.

        3. Mae*

          I have a short torso. I will never tuck in. Men shouldn’t have to, either, as long as they don’t wear oversized, frayed shirts down to their knees.

          1. AnotherAnon*

            Yeah, tucked-in shirts make it look like my hips connect directly to my breasts. :P and also like my mother picked out my clothes.

            Plus, the moment I raise my hand above my head (which is a common thing when you’re short) the shirt un-tucks itself. If I’m really unlucky, a roll of fabric will get stuck above my breasts too. :/

            unfortunately I can find plausible explanations for the shoes and hems too… hopefully this guy doesn’t have actual problems with all of them. (at the very least, he probably won’t have the breast-related problems ;)

          2. GreyjoyGardens*

            Short-waisted gals represent! I’m the trifecta of petite, short-waisted, and apple-shaped, so if I tuck in, I look like a beach ball on stilts. A waist-skimming tunic top that hits at or slightly below my hips is so very much more flattering on my body type – as well as being more comfortable! Tucking in feels bunchy and weird to me.

        4. always anon*

          Not really. I’m thin, but unless it’s a very, very fitted shirt, tucking it in leaves a lot of excess billowy material around my waist that makes me look boxy. If I want to tuck a blouse into a skirt, I usually have to wear nylons or tights or pin the material to the skirt. When I worked retail in high school, I hated wearing tucked in shirts because there was so much excess material for some uniforms that it just created a weird bulge around my waist/hips/stomach.

          Also the problems of a larger chest and very thin waist meant that I looked like a box no matter what because those tucked in shirts are not flattering at all.

        5. Murphy*

          Yeah, I love, love, love the look of a nice blouse tucked into dress trousers, but I cannot pull it off (and it makes me look way more frumpy and poorly dressed). So untucked blouses it is!

    1. Roly Poly Little Bat-Faced Girl*

      And I’m short-waisted, so leaving a shirt untucked helps balance out the proportions of my body.

      1. Mae*

        +1. Off topic, but I envy those with long torsos. I find it hard to be business professional and feel confident at times. Luckily, I can get away with a nice top and pants. Suits only for meetings, but ugh.

        1. CMart*

          Continuing with your off-topic, but it’s a no-win situation with torsos. It’s a serious struggle for me to find any shirt that reaches my pants, or dresses/skirts that don’t widen out for the hips inches above where my hips actually are. Tucking in shirts is the worst since at best I have a centimeter or two of fabric to tuck, so the slightest movement will untuck me :(

          1. many bells down*

            Yes! I have a long waist and I just can never really get anything to stay tucked in unless my waistband is pretty far up. I always figured I just moved my arms around too much.

          2. sam*

            Ugh. I’m super long-torsoed, and have super short legs, and it’s always been an issue. Everything from buying swimsuits when I was a kid (until they finally invented tankinis) to buying pants as an adult (why yes, I love when the waist only reaches mid hip but the legs go past my feet, doesn’t everyone?), to that era in the early 2000s when they ONLY made hip hugger pants and shirts that were short-waisted (thank god that ended – I literally didn’t buy clothes for several years).

            Fun story – After I graduated from law school, I decided to go on a bicycle trip through france after the bar exam. They give you the bike for the trip, but ask you to send your measurements – height, inseam, etc. so they can get the general fit of the bike correct before you get there. When I got to paris, with only a few hours to spare before catching the train to our first departure point, the bike mechanic was FRANTIC to meet me, because, in his words “the measurements I sent were all wrong”. You see, he saw the measurements for my height and my inseam and basically thought it was impossible for someone to be my height with legs *that* short. So he remeasured me. Twice. and then looked at me and apologized. Because the measurements I sent were correct. I joke that I’m just like Michael Phelps, except I’m a short plus-sized 42-year old lady.

            1. many bells down*

              One-piece swimsuits are so disappointing. It’s cute but then you spend all your time trying to keep it out of your butt. There used to be a catalog company that offered swimsuits in long torso, but I think they’ve long gone out of business. I don’t care how old I am, I am never ever giving up a bikini.

              1. Jaydee*

                Pull it up to cover the boobs. Pull it down to avoid the wedgie. Repeat every couple of minutes.

              2. INTP*

                I’m 5’2″ so the torso length is fine despite my proportionally longer torso, but I have not been able to find one that isn’t obscene in the boob department. Most one pieces are less supportive than bikini tops because they don’t have a band. Even if they’re designed with support, you can’t buy a different size top, so if you are large chested you’re either basically wearing pasties on top, or sagging at the butt.

                1. Amadeo*

                  Might I suggest websites like Bare Necessities, bravissimo, Her Room and so on. I have to order my bathing suits with cup sizes and underwire (they make bikini tops that way too) because, boobs. Like, 36H. Swimsuits off the Penney’s or Macy’s rack just don’t cut it.

                2. Raine*

                  There are two more options you might try:

                  1) Sports-types of swimsuits (I mean almost for competitive swimmers). And I’m not one. But most swimsuits either have no support at all or weird almost 1950s rocket-bra support that you can’t cut out. But there are racing suits that somehow manage to provide the support, especially if the neck is high and showing almost no or no cleavage at all.

                  2. Rashguards. Either over a suit that you otherwise can’t wear in public, or even over a bra-sized bikini top or actual bra. (Then on bottom whatever you want in a swimsuit bottom or skirt.) And even though I don’t have a long torso, I usually buy rashguards made long rather than regular — this is because my bigger boobs take up more space and so (especially with any belly at all) my shirts wind up shorter than I like.

                3. Bob Barker*

                  I feel this pain. I spent several years wearing a black sports bra under a black one-piece (for both coverage and support), and it was obvious and ridiculous, with the clasp sitting well above the back of the swimsuit.

                  I bit the bullet and switched to tankinis. They’re stupidly expensive above a certain bust size, but the whole “I lost a wrestling match with a slip of nylon” experience is not one I’m interested in going back to.

              3. Fed Up*

                Land’s End has some great sizes (the regular ones, plus tall, fat, tall & fat) in one-piece, tankini, and separates. And LE has really good customer service.
                Also check out Sears; they showed up in my Bing for “women’s tall swimsuit”.

            2. nerfmobile*

              Yep, that’s me. My husband (of more normal proportions) is 3 inches taller than I am – standing up. When we sit down side-by-side, the tops of our heads are at the same height. So the entire 3 inches of difference is in the legs!

              1. sam*

                3 inches? that’s nothing. when sitting, my dad and my brother could balance a level on top of both of their heads and it would, well, level. When standing, my dad is 5’8 and my brother is 6’3. Walking anywhere with my brother is quite possibly the most annoying thing on earth, because you have to take 2-3 strides for each of his. He got ALL THE LEGS in our family.

                (for reference, I am 5’4).

                1. Clever Name*

                  Yeah, my husband is 7 inches taller than me, but we both wear a 30 inch inseam, so….

            3. Tabby*

              Haha Michael Phelps body. I sort of have that in reverse! Narrow shoulders, wide hips, big butt and a short waist. Oh and I am overweight. Clothes buying is always… interesting. I finally just started wearing shirt dresses only (tshirt, more formal button downs, tunic style). Amazingly, they always fit perfectly and I don’t have to tuck in a dang thing. I am happy with this.

          3. INTP*

            My torso problem is finding jeans with a high enough rise. This probably has to do with fat distribution too, but I cannot for the life of me find midrise jeans or pants that don’t ride way down into muffin top territory (if not exposed coinslot territory) that also come in a petite length. I wear AE sky high jeggings with a long top (my work is super casual) or just skirts and dresses.

          4. Murphy*

            This will be my daughter (unless her proportions change). She’s only 20 months old but wearing size 3T clothes (and even some of those shirts are a little on the short-side). I refuse to put my child in a belly shirt (she’ll display her belly all on her own, no need for me to help).

        2. A Girl is No One*

          I used to envy them too, but then I started competitive weightlifting and soon discovered the elegant long waisteds were envying ME. So empowering! Shorties rule! (I’m barely over 5 ft, I can deadlift 300lbs.)

          1. AnotherAnon*

            thank you, I was avoiding the gym because internet, and now I actually *want* to go to the gym :) I don’t think my hands are healed enough for deadlift, but I can sure as hell squat. :)

    2. Trisha*

      OP here again. I don’t think that I would notice the un-tucked shirts if he looked neat overall. For what it’s worth, the employee is very slim. I’m trying to find an example that would make sense … he kind of looks like Shaggy from Scooby Doo, only envision collared shirt and khakis rather than t-shirt and jeans (?).

      1. NJ Anon*

        Could it be his build? My son is tall and thin. He never really looks put together. That’s no excuse for the frayed hem but shirts just never seem to fit him properly.

        1. aebhel*

          That’s me and my brothers as well. We’re all very lanky–broad and long-limbed, but thin–and clothes just hang off of us no matter what. I can get around it because women’s clothes have more variety, but my brothers look sloppy even in a suit.

          Sounds like this employee is pushing the envelope in a lot of ways, though…

          1. Trisha*

            Yes, I think it is the whole package. He’s tall and slim. He wears a loose shirt un-tucked, sometimes throws a worn looking sweater overtop. He usually slouches. Again, none of this affects his job performance. I notice it, but it isn’t a deal-breaker. However, it makes my boss nuts. It is seriously limiting his upward mobility here. I want to help him without offending him, which is why I contacted Alison! :)

            1. Hotstreak*

              It sounds like he could benefit from a good tailor, getting a shirt brought in isn’t as expensive as people assume! I completely understand his shoe choice, sneakers are obviously 3x more comfortable than dress shoes. I found a balance in a brand called Dunham (by New Balance). They’re ultra supportive and comfortable like a quality athletic shoe, come in wides, and have nice leather uppers.

            2. (Not an IRS) Auditor*

              Sounds like my baby brother (now 30ish). Though he’s starting to not be as thin as he used to be.

            3. Not So NewReader*

              I think you are on to something here. Look at what you just said, limiting his upward mobility, not offending him…. Useful stuff.

              “Bob, I need to talk to you about something. I think you have some serious potential here, but you have something that is holding you back. You need to beef up your appearance, Bob. Clothes should not be too wrinkly, and definitely no frayed stuff or stuff with holes in it. And the company prefers that we wear something other than sneaks. I really did not want to say anything because it feels like a personal comment. However, any company you work for will have a dress code and it’s important to know the dress code and follow it. If we don’t think about our appearance at work, it can hold us back. And that is what is happening here. My goal is for everyone in our department to be successful and it’s my job to tell people what it takes to be successful here. On the good news side of things I think you can be successful with this company.”

              I’d provide him with a written copy of the dress code, also.

              It may sound like a compliment sandwich, but there is one thing here, it’s not random compliments. The compliments are part of the story, if his work was crappy, this entire conversation would be different. But he does good work, it’s this one side issue that is a slowing down his deserved progress.

              To motivate myself the day of the conversation, I would remind me that if I do not do this then his failure at the company is on ME in part. Ugh. Ugh. On the plus side, sometimes these candid conversations can lead to other conversations later that only two people who TRUST each other could have.

              1. michael snow*

                If any manager had ever told me that when I was an employee, I would ask them straight “Am I breaking the dress code?”

                In this case, it sounds like the answer would be “no”

                So then I’d tell them, “If the dress code doesn’t reflect what the company wants me to wear, then change the dress code
                If you want me to change what I wear, change the dress code
                If I’m being judged for things other than my ability to do my job, put it in writing in my job description”

                If the answer was “yes”, then I’d say “Thank you for letting me know. Please could you put in writing which parts I’m breaking and I’ll deal with them”

                There are many people in the world who hate clothes, don’t understand style and wear the exact minimum to comply, while being excellent workers
                If you penalise them for breaking rules they don’t understand or are not aware of, you are shooting yourself in the foot

    3. Koko*

      FWIW the fashion powers have declared untucked shirts en vogue. Men’s dress shirts are now often made shorter and with neater hems specifically because fewer men are tucking their shirts.

      Of course, you still need to take your cues from the people in your own office and what they’re wearing. But tucking in shirts seems to be going the way of pantyhose and big church hats – ain’t nobody that fancy anymore.

      1. Talvi*

        I like to think I am singlehandedly trying to bring hats back :) Not church hats, per se, but just wearing nice hats when out and about. I get a lot of compliments for my hats, and I think this is tied to the fact that you don’t see people wearing hats much anymore. It makes me feel very put-together.

        1. cataloger*

          I always wear a hat, and get so many compliments from strangers! My dad liked my hat so much that he got one just like it, and now he gets loads of compliments too.

    4. EmmaLou*

      Yes! this is what I thought as I read. No, no NO! Don’t tuck in a polo! That hem is bunchy and looks bad tucked in. And you look weird and out of touch. It can still look professional (casual) and not be tucked in. You know, not wrinkled or bunched above your tummy.

      1. Rusty Shackelford*

        Wait – are we officially okay with the untucked polo as business casual now? I never tuck my shirt in (short and apple-shaped) and I’ve been avoiding the polo-and-khakis uniform for trade shows because I didn’t want to have to tuck in a polo. I’ll have to start paying attention and see if this is accepted in my part of the world. (Crossing my fingers!)

    5. Rosa*

      An untucked dress shirt over men’s dress pants is giving me terrible mental images. I can’t imagine that looking good at all.

      1. Bulbosaur*

        Oh, but it do, it do. You just gotta get the length right. Can’t do it with one of those dress shirts that’s long enough to be a tunic.

    6. Ever and Anon*

      You can get these garter-like contraptions that clip a shirt to your socks to keep it neat. I wonder how many super -put tofether-looking suits and uniforms are kept in place by such devious means!

      1. BananaPants*

        I was a Sea Cadet in high school and with certain uniforms we wore shirt stays. They clipped to the top of socks and ran all the way up to the bottom of the shirt. Kept them tucked in perfectly!

      2. Bob Barker*

        Ha. This is why men didn’t need underwear for a long time in history. Their shirttails WERE their underwear.

        If the waistcoat (with braces, not a belt, underneath) were to come back into vogue, I wouldn’t object in any way.

    7. ancolie*

      Ugh, me too!

      I’m really curvy (fat, yes, but extremely hourglassy) and reaaallly short waisted. Tucking a shirt in (esPECially with pants) is basically the worst look I can have. I turn into a stubby fire hydrant because my waistline is completely hidden by the tucked fabric. It also makes my lower belly suddenly take the spotlight. Ugh.

      1. Isabel C.*

        Also short-waisted and I would add that, if the shirt is too long, you either end up with the waistless way-too-blousy look or a weird diaper-y thing going on with too much fabric underneath your pants. Either way it’s Bad News.

    8. Birdie*

      I am most definitely someone who wears tucked in shirts. When I’m at work or working out I just feel so much more comfy with the shirt tucked in. Of course there are exceptions though. Some shirts were not meant to be tucked in.

    9. Elizabeth West*

      I can’t stand to tuck in my shirt, and I hate belts (they press my messed-up stomach and actually can hurt). Luckily, many women’s blouses are made with a straight hem and sometimes a little slit at the sides and are meant to be worn untucked. Most of the time, I wear a t-shirt and jeans, but this is a big help when I have to go business casual.

  4. Lizabeth*

    This describes me at times for one major reason – I don’t get my laundry hung up in a timely manner to avoid wrinkles.

    1. Christopher Tracy*

      And you don’t iron or use steamers? No snark – genuinely curious.

      If I’m running errands on the weekend, I don’t care what my clothes look like. But at work? If I see wrinkles, I bust out the iron (even though it’s a pain in the ass time-suck and I’d rather not), and I’m not in a customer facing role either.

      1. Artemesia*

        At most times of my life, I would have been hard pressed to locate an iron in the house. Right now I could not do it; not sure we actually still have one. But when you are ironing averse you learn how to manage clothes so they don’t need it. (we just sent my husband’s shirts out and still do, although not working now means he needs fewer ironed shirts in any given month)

        1. Christopher Tracy*

          I like the spray-on wrinkle release suggestion below. I hate ironing/steaming things (hence why I try to buy dresses that don’t require it), so if that stuff works, I may have to try that until I can afford to have stuff sent out on a regular basis. That will be wonderful.

          1. LawLady*

            It does work! It’s not perfect, and it won do collars just so, but for your average shirt or blouse, a few spritzes, a few tugs, and it’s good enough.

        2. NJ Anon*

          Ditto. I have an iron somewhere but never use it. Out of the dryer and onto a hanger!

      2. Manders*

        I try to choose work clothes with fabrics that don’t wrinkle if they aren’t steamed or ironed, because I just don’t have the time and energy to get that done regularly. This is one of those dress code issues where it may actually be more convenient to be a woman, because I have a broader range of styles and fabrics to choose from while still looking professional.

        The frayed hems are over the line, though. Work clothing shouldn’t be visibly damaged.

        1. The IT Manager*

          Ditto. I mostly pick clothes that don’t require ironing and I take them out of the dryer right away because I don’t want to hassle of unwrinkling them. IMO both of these decisions make my life easier since I rarely have to iron clothes.

        2. Cat Boss Meme*

          The only thing my husband wears to work are lightweight polos and dress pants, like some kind of knit blend or something. Out of the dryer, right onto the hanger, yes! They make polos in this terrific waterwick fabric or some thing that you don’t even sweat in! In the winter, maybe a thin knitted v-neck. We live in the Deep South. I am SO envious! I try to buy clothes that don’t require dry cleaning, but even pulling out a big ironing board to press a pencil skirt in our crowded apartment is a huge pain. Men have it SO much easier when the dress code is business casual.

          1. Stitch*

            Yeah, my boyfriend does the same polo (I think they’re called golf polos?) and dress pants thing – for casual wear, he just switches in cargo pants. He pairs it with military boots that don’t look awful under pants, though they are pretty scuffed at this point. He really likes Izod because they don’t seem to ever wrinkle, and his pants still seem to have a crease in them even though we haven’t ironed them probably ever. Though, Izod is getting harder to find, so I’ve stopped complaining about how hard it is for me to shop compared to him. Women clothes do have more variety, but I’ve nearly broken down in tears over not being able to find something that fits both the dress code and my personal comfort level before. I think a lot of my stress comes from not knowing where the lines are drawn – it’s pretty hard to toe the line when business casual has so much variety across different companies/situations.

      3. Lizabeth*

        The only time I bust out the iron is to press seam allowances while making a quilt.

        1. many bells down*

          I pretty much only use my iron for sewing as well. I have a travel steamer that takes 30 seconds to heat up that I use if I have to de-wrinkle something, which is rarely.

      4. addlady*

        I learned to hang up clothes right outside the shower to remove wrinkles. Sometime I might even try it. :)

        1. Windchime*

          I’ve tried this a few times and never could get it to work. People say it all the time, though, so it must be working for someone!

          1. Camellia*

            I think it worked better in the days when there probably weren’t vents in the bathroom to remove the steam generated by a hot shower. Also, fabric content matters too.

          2. the gold digger*

            My husband hangs his button-down shirts up after they have been in the dryer only long enough to get hot. They are still damp when he takes them out. He hangs them up (on a hanger with bumps on the angled part that I am not supposed to use for my shirts because they are the Good Hangers), smooths the collar, the placket, the cuffs, and the pocket with his fingers, and pulls the seams down. They dry really nicely and rarely need ironing.

            (Yes, he is an engineer, why do you ask?)

      5. MashaKasha*

        Ugh, I cannot stand ironing things, but I don’t know of any other way to keep dress pants and dress shirts, and even khakis and slacks, wrinkle-free. Luckily, no one in my household currently wears any of those, except to court hearings and funerals. I got around my employer’s dress code by wearing cords. It will be a sad day when they tell me to switch to dress pants or slacks.

        Weirdly, when I was in high school, ironing was one of the few chores I had around the house. I could iron a dress shirt for my dad with my eyes closed. Now I’m ironing-averse, go figure.

        1. Unegen*

          Try a garment steamer. It takes the wrinkles out of things (even things you’d never iron, like cashmere sweaters) but does not leave fabrics shiny the way an iron can. However a steamer cannot put a crease in a garment. Best $60 I ever spent on Amazon; I haven’t used my iron for at least five years.

      6. Ellie H.*

        I love ironing! For me it’s one of those chores that you find really relaxing. I find it so satisfying to make everything smooth. I have a ton of iron-requiring clothes too (all from Boden basically) even as a late-20’s-er with a fairly casual workplace. It’s not a lost art! It is key to have a good iron and board though.

      1. Megs*

        Knits (almost) never wrinkle! I don’t think I’ve ironed anything since I was living with my parents.

        1. Lizabeth*

          The polo shirts will generally hang out the wrinkles, however, if I’m grabbing straight from the laundry basket – wrinkled!

    2. Cambridge Comma*

      When I was a kid, everything in the household got ironed, but it seems to have died out. I haven’t ironed anything in 5 years. Is it technology?

      1. BRR*

        Maybe fabric technology, An advancement in wrinkle-free fabrics haha.

        I just steam my work clothes. Anytime I iron something I seem to add no less than 3 creases to the article of clothing.

      2. Trisha*

        I do not iron unless it is a very important meeting I am going to! I buy clothes which typically do not need to be ironed and hang everything up, when possible.

      3. Megs*

        I think it’s probably just a part of the gradual loosening of formality that’s been happening since the 60s (50s?). Which, to be clear, I am totally okay with.

        Example: it used to be common to require law students to wear a suit while taking the bar exam. Now I want to say Virginia is the only place to require it because everyone else realized that there is no reason to wear anything but the most comfortable of clothing while spending two days in a stuffy gym with 500 other people desperately typing away.

        1. Triangle Pose*

          Virginia is the worst! You have to take the bar exam in a full suit but you can’t wear shoes that make noise so no high heels to go with the suit. Our year my SO told me there were a lot of women wearing full on suits with sneaker type shoes. It’s a ridiculous hard line for the VA Bar Examiners to take.

        2. Natalie*

          I would guess more singleton households and coupled women working outside the home is a factor, as well. Doing a shitton of ironing is a lot more feasible if one partner can make it part of their fulltime housekeeping job.

        3. MashaKasha*

          I just thought that it might be also the gradual widening of closet space. I live in a 50s house and the closets are tiny, fortunately we have an extra one in the basement. Otherwise the clothes would’ve gotten all smushed together and wrinkled; or we’d have to fold them and store them on shelves, where they would again get wrinkled. In the few older houses I’d been to, closets are even smaller. No walk-in anything.

      4. always anon*

        Honestly, I usually just take a very hot shower and leave whatever clothing needs to be ironed on the back of the bathroom door. The stream gets all the wrinkles out without me having to do anything.

        1. SophieChotek*

          Hmm. I should try that. I hate ironing, but almost all my dress shirts require it.

        2. Unegen*

          The downside of that is that over time all of the unvented steam does a number on your drywall. Buy a garment steamer and save yourself the home repair.

      5. Talvi*

        I don’t know, I still iron just about everything… Even my jeans and chunky knit sweaters (which really don’t need ironing). Nothing goes into the dryer except towels, socks, and pyjamas.

      6. Rusty Shackelford*

        I have a couple of linen shirts that have to be ironed, and one woven cotton shirt, but that’s all. Twenty years ago I ironed almost everything I wore. I don’t know if fabrics have changed, or my shopping habits. Or if my standards just slipped. ;-)

      7. Bob Barker*

        I still iron a ton, but I’m a bit old-fashioned on that front, and finicky about fabrics.

        In addition to shifts in fabric and formality, it’s the fact that so much clothing can be put in the dryer now. 99% of what I iron is hand-wash (silks), or line- or flat-dry stuff like wool and most linen. (I put a linen skirt in the dryer by accident recently, and it survived, so…?

    3. Edith*

      Pro tip: If your clothes are wrinkled because you don’t get them out of the dryer in a timely manner, run the machine for 10 minutes right before you put the clothes away. It’s like a reset button.

      1. Beezus*

        I do this all the time! I have a few stubborn things that it doesn’t work for; those I either toss back in with the next wet load, or by themselves with a damp washcloth. It’s like they need the wet heat for the wrinkles to release, and dry heat just won’t do it.

        1. Liane*

          It is the damp washcloth! I use this a lot. I try to do as my dad taught me and take out dress shirts/slacks and other wrinkle-magnet clothing out when it is still damp and hang it–but often it doesn’t happen. Then the damp wash cloth saves the day.
          Also, setting a timer near me helps me remember to take the clothing out–if I don’t get so absorbed in a book or the internet that I don’t hear it or just ignore it.

          1. Anxa*

            I like a damp square of flannel as the rag. Until I’m rich and can buy one of those steamers, this is my ironing solution.

        1. Windchime*

          Yes, so does mine. I love it. It puts a little moisture into the dryer as it’s going. I never thought I would use it but I kinda like it.

      2. KTM*

        Yep that’s what I do. And if I have a wrinkled shirt from the closet, I’ll just pop it in the dryer for 10min with a towel or something and it works the same.

      3. Lady Kelvin*

        I was just coming to say this. And if its something that can’t be dried, hang it in the bathroom and take a hot shower without the fan running, when you get out pull the wrinkles out slightly, it’ll make a major difference with minor effort.

      4. Cafe au Lait*

        I throw in a cup’s worth ice cubes and rerun the dryer if I’ve let my clothes sit too long. The melting ice steams the clothing and dewrinkles the material.

        1. Library Director*

          An ice cube is brilliant! I have cut up kitchen sponges that I use (they’ve never done kitchen duty). I dampen one and throw it in. I usually add in a towel as well. If it’s winter I may put a miniscule amount of hair conditioner on the sponge to help with static electricity.

      5. Blurgle*

        One of the things I miss about living in a house was the ability to turn on the dryer for ten minutes.

      6. Rusty Shackelford*

        My dryer actually has a permanent press setting that does this automatically. If you don’t take the clothes out, it will start up again for a minute. And it will repeat this cycle many, many times.

    4. TootsNYC*

      Can’t you just lay the shirts flat when they come out of the dryer? That goes a long way!

      I nearly divorced my husband over his not hanging up my work shirts to keep them from being wrinkled. (He was just shoving them into the laundry basket and letting them get creased.)

      It wasn’t quite that simple–I was ultra stressed at work, the sole wage earner, and since he wasn’t looking for work, all I wanted was for him to hang up my clothes when they came out of the dryer. Even after I made it clear that I was considering it a “do you really support me?” issue, he couldn’t do it. Well, he did it twice and then never again. Instead, he left them in the laundry basket, at the bottom, with everything jammed on top of it, to get phenomenally creased.

      I finally had to say to myself, “Do you want to get divorced over this?” And I gave up, and now I do my own laundry. But that damage is still lingering, like a soft-tissue injury.

      1. MashaKasha*

        You just described the reason why nobody can touch my laundry. They are not going to do it right. They’re welcome to do their own, but please stay away from mine. I’d be livid too if someone washed mine and then just shoved them in the basket haphazardly!!

      2. Murphy*

        Yeah, that gave me hives just thinking about it. I can totally see that being a hot-button issue with me as well.

      3. K-VonSchmidt*

        I threw away our laundry baskets. Problem solved, you now must FOLD or HANG everything.

    5. BuildMeUp*

      If it’s just light wrinkling, you could try hanging up whatever you’re wearing that day in the bathroom while you shower – the steam will help!

    6. Camellia*

      I have a dryer with a “refresh” cycle. Toss it in and in a few minutes wrinkles are gone. I love it!

    7. themmases*

      Huh. I just hang them to dry. Shirts I do this to don’t end up looking pressed or anything, but they’re never really wrinkled. They kind of end up in a space that is fine for a casual day (my office is very casual) or easy to press for a formal day.

      As a bonus, this means I can spend time hanging them up when there was nothing else to do anyway since all my other clothes are still in the dryer.

      I put them on hangers from my shower curtain rod and leave the bathroom fan on, works year-round.

    8. BananaPants*

      I buy wrinkle-free fabrics for that very reason. I used to have the time to iron my clothes for work, now I just don’t.

      I get jealous of my husband, who can wear SCRUBS to work. It’s like going to the office in your pajamas.

  5. Rebecca*

    I’d be concerned that the employee was housing challenged, and/or has limited options for laundry and other hygiene processes. It’s possible he’s couch surfing or living out of his car, and this is a side effect. As far as the frayed pants and not up to par shoes, is it possible he can’t afford new clothes?

    I know I’m going out on a limb here, but there could be other things afoot other than he’s pushing the dress code.

    1. AnotherAlison*

      That sounds like a stretch to me. I work with dozens of people who dress like this, and earn $60,000-$100,000 salaries. Stereotypically, technical people don’t put a lot of effort into appearance. I’m in an untucked shirt today myself.

      1. Poorish*

        Also noting, there are people earning that much that have all their earnings going towards (debt, child support, ransom demands) and can’t afford to buy new clothes.

        A huge thing for me is that even though I make $40K I haven’t bought more than a handful out clothing items in the past 3 years. I cannot afford it, I can barely afford groceries… Nothing is worse than being told at work that you cannot wear a shirt that is a bit stretched or pants with frayed bottoms when going out to buy a new pair means I won’t eat supper one night. Last winter I had to walk home from work oneday with half my foot popping out of my boot – I had to wear sneakers for weeks!

        I am the caregiver for my husband and hold down a full time job. If I am clean and look half decent then that should be good enough unless my benefits can include an extra payment for more polished clothing.

        1. Not Karen*

          The payment for clothing is already included in your salary. I’m not saying this is your fault or this is fair, but a clothing allowance is not the reason you should be getting 42k instead of 40k; it’s the reason you’re getting 40k instead of 38k. I assume others in your position at work are also getting 40k and have the same dress standards.

          1. Beezus*

            I think Poorish’s comment was intended to highlight that just because someone’s earning what most would consider a decent salary, doesn’t necessarily mean that they have disposable income. Different people have different life circumstances; what’s plenty for one person might mean hard times for someone else.

            And while true business needs are business needs regardless of an employee’s circumstances, I’d expect a manager to take circumstances like the ones Poorish described into account, and apply some flexibility where it made sense. It’s usually possible to get business needs met and treat people with a modicum of kindness while you’re at it.

    2. Kyrielle*

      Possible, and OP should probably keep that in mind and bring the conversation up in ways that allows him to say “I can’t” if he needs to – but he still could tuck his shirt in, and that would help a little, so letting him know is still useful.

    3. KellyK*

      There certainly could be, although I think AnotherAlison is right and a lot of tech folks just dress that way.

      I think the only thing that possibility really changes is that the boss shouldn’t push him to buy a bunch of new clothes and should be willing to work with him if he brings up problems. Tucking in his shirt is something he can do right away for free. If it’s going to take him a while to afford new pants or figure out where to hang up clothes in tight living quarters, his boss should be patient.

      1. Megs*

        I like the idea of suggesting things that don’t require him to buy new clothes – even if it’s not a financial issue, it might be met with less resistance. Wrinkle-free clothing, tucking in shirts, even trimming dangling hem should be manageable.

    4. Trisha*

      Letter writer here! This employee is not at all housing challenged, he makes a good salary and owns his own home. It is more like AnotherAlison describes. I do not have any reason to believe there is a financial issue going on here.

      I have noticed this problem, but it is my boss that is really bothered by it. This employee also meets regularly with director-level folks. This kind of sloppiness does affect your credibility with people, whether I like that or not!

      1. Sharon*

        I have a coworker that sounds like your employee. I sometimes wonder how his wife lets him out of the house looking the way he does. He’s always clean, but always wears poorly-fitting, baggy clothes. Once a year my company hosts an international conference and he had to speak at it a couple years ago. He wore a business suit… that looked like he bought it from the Salvation Army and it was the only size left. Nobody says anything to him (including me). I figure he just doesn’t realize how he looks. Or doesn’t care.

        1. CMart*

          “I sometimes wonder how his wife lets him out of the house looking the way he does.”

          If it’s anything like my household, his spouse says “Your shirt is really, really wrinkled. Shouldn’t you iron that before you go to work?”

          Him: “Meh. It doesn’t matter.”

          1. Spike*

            I’m not my husband’s mommy. He can dress however he wants.I won’t let him leave with his butt hanging out or anything that could get him arrested, but other than that, if it’s problematic, it’s on him.

            1. Mononymous*

              Ditto. My husband has slob tendencies and I really don’t care for the way he dresses a lot of the time, but I made a conscious decision early on that I could not and would not act like his mommy in this regard. It would be disastrous for our relationship if I tried. He’s a grown man and can figure out for himself if wrinkled or holey clothes are holding him back at work.

              1. MashaKasha*

                Yup yup. Do not do to others what you wouldn’t want done to yourself. I wouldn’t want a husband or a partner to look at me and go, “You’re wearing THAT?” By the same token, I’ve left it up to my husbands/partners to decide what they wanted to wear. It really would be disastrous for a relationship.

          2. Megs*

            In my house, it is generally expected that we will point out if someone is wearing something with an unnoticed stain or tear, if someone’s fly is down or skirt is tucked into one’s underpants, and that’s it. Very occasionally one might raise an eyebrow and ask: “are you sure about that?” Duties accomplished!

        2. Triangle Pose*

          He’s an adult. His wife isn’t responsible for his appearance. If he is representing your company at the international conference, why doesn’t his manager say something to him? It likely looks bad for your company to have someone representing it as a speaker at an international conference who can’t wear a decent suit.

        3. Laura*

          “I sometimes wonder how his wife lets him out of the house looking the way he does.”

          Don’t put this on his wife. He’s a grown-ass man, not a 5-year old.

        4. Observer*

          I sometimes wonder how his wife lets him out of the house looking the way he does.

          I suggest you turn the pronouns around, then see how it sounds. This kind of thing is not just infantilizing, as others have noted, but also very sexist.

        5. Oryx*

          “I sometimes wonder how his wife lets him out of the house looking the way he does.”

          Is he 8 years old and needs mommy to dress him?

          And, I leave the house before my boyfriend. I don’t know what he wears to work until I see him that evening. He’s an adult, he can pick out his own clothes.

        6. Nervous Accountant*

          Maybe because the wife is not his mother and he’s a fully grown adult capable of dressing himself

        7. Dangerfield*

          Really? My partner quite often leave the house looking like that. He doesn’t care how he looks. He’s a grown up, and I’m not the fashion police. Nor am I his mother. Women are not responsible for men’s adherence to social rules.

    5. BRR*

      It’s a possibility but why would that be the first thing to jump to? It’s not to say you shouldn’t consider explanations for things but to reference the commenting guidelines it’s not practical advice for dealing with the person in question anyway.

    6. Koko*

      The frayed pants are undoubtedly linked to the fact that the pants are also baggy. If the pants are too big the hems drag on the ground and get underfoot. I have jeans that I’ve owned for 5 years that aren’t frayed because the hems don’t touch the ground, but when I was a teenager and baggy/grunge was in (bless you, 90s) all my pants would have frayed hems within a month of purchase.

      1. Ife*

        Or he is short. Until skinny jeans became popular I could not for the life of me keep my jeans from getting frayed, because even the “short” jeans were made for people 2-3 inches taller than me!

        1. KR*

          I used to have good luck at Hollister and American Eagle for “short” sized jeans. This season is too long at both stores though :(

          Signed, Someone who is 5 ft tall

          1. Clever Name*

            A coworker once asked me where I find my jeans since mine are always just the right length and I’m short. My response was, “Oh honey, I get all my pants tailored” Does it suck? Yep. But I want to present a professional image, so I make an effort.

            1. Bulbosaur*

              I have to get everything tailored – pant length, skirt length, straps shortened on dresses. It is infuriating paying for clothes twice – once to own them and once to actually be able to wear them. If I were four inches taller I’d save a fortune.

            2. AnotherAnon*

              the crazy thing is, even pants I’ve had tailored often drag on the ground. even when I ask them to err on the short side.

              maybe I should start going back to them and demanding they redo it or give me a refund? but not only am I not sure that’s okay, it would be another drain on my time and energy.

              I did try hemming one pair myself, but without a sewing machine it’s pretty time-consuming, and I get lots of irrational anxiety about screwing it up. *sigh* I’m glad I haven’t been in a position where anyone would care.

              1. Fed Up*

                Yes, definitely make them do it to the standards you stated when you were hiring them. If that means having a couple pair re-done before they figure out that yes, you really did mean you wanted them to be 26.5″, not 27″, well, you’re both losing time & money in the re-do. Or if they can’t figure that out, if it takes more than one re-do, find another tailor. (Or a uniform shop.)

                Or if you don’t want them to measure the length for you, you measure similar pants that fit you well, tell them that inseam (or outseam, whichever you prefer, but make sure they know which, and if it’s outseam is it from the top of the waistband or the bottom), and when you go to pick the new ones up take a tape measure with you. Measure them right there at the counter. Don’t pay until it’s right.

                OTOH, make sure the directions / measurements are clear & accurate the first time, on the order that’s going to the seamstress / tailor, to prevent problems up front. Much less frustrating all around.

                I’m a seamstress at a uniform shop, and some of the directions from the sales people are unbelievable… Last week, on some dress jackets, the sales guy said “shorten sleeves”. That was it.
                On all of the jackets or one of them? By how much? By the same amount on both sleeves of each jacket? Or how long do you want them to end up? Measured from where? (The sleeve cap or underarm seam would be normal & reasonable, but apparently he measured from the center back neck seam!)

                And doing them yourself is not difficult, just takes time.
                And pins. Pins help keep the fold at the bottom where you expect it to be.

          2. Christopher Tracy*

            Did you try ordering your jeans/pants from AE online? I do that when I can’t find the right “short” size in store.

      2. Talvi*

        That’s easily fixed, though. A sewing needle and some thread, and maybe someone to help you pin your hem to the correct length. I’m short (5’2″), so I have to hem every pair of pants I own except skinny jeans for just this reason.

    7. themmases*

      Maybe, but how does this change what the manager should do about it? All it really means is that when they raise it they should be tactful, which would be the right thing to do either way.

      If the employee in this letter has some personal circumstance that makes it hard for them to meet the dress code, then it’s their choice whether they want to tell their boss or just handle it alone. They may want to keep that part of their life private (there was a letter writer here like that, actually), in which case they need to know that they are not passing even if they never tell their boss.

    8. LizM*

      I don’t know. My husband hates shopping and hates spending money. He would wear clothes until they fall off him if I didn’t discretely throw them away when they hit the “too stretched out or frayed to be acceptable in polite company” stage. Some people honestly don’t notice when their clothing is starting to look worn out or frumpy.

      I mean, in situations like this, it is always helpful to go in in an empathetic manner, but I wouldn’t assume everyone who is poorly dressed is dressed that way because they don’t have disposable income.

  6. Kvaren*

    “He wears shoes that are the ambiguous type that are sneakers but meant to pass as shoes.”

    I just want to point out that in the Venn diagram of footwear, the sneakers circle is completely within the shoes circle.

    Kidding. I figure the OP meant “dress shoes.”

    1. Murphy*

      Mmm, I’m gonna put those weird toe shoes/runners on the outside of that circle. The good name of shoes should not be sullied by those monstrosities.

      1. Isabel C.*

        Ugh ugh ugh yes. I had a friend (no longer one, for reasons ironically related in part to being judgmental about other people’s dress choices) who wore those to parties, like the sort of party I’d put on a dress for. UGH. NO.

    2. CMT*

      I have a coworker who wears SLIPPERS, that he thinks are okay because they are black and kind of mocassin-type-y. You can tell from a mile away that they are slippers. But that’s like, the least of his professionalism problems.

  7. Clever Name*

    I think I’d be even more direct and specific. As in instead of phrasing it as “wear less casual shoes” you may need to say, “I need you to wear shoes that are made of leather/leather-like material that have leather or hard soles. Rubber soles or fabric uppers aren’t allowed.” He’s probably wearing Sketcher-type shoes and thinking, “These aren’t white sneakers, so they’re good for work!”

    1. Not Karen*

      Although hard and fast rules like that may not work… I have shoes with fabric uppers that pass as dress shoes.

      1. Clever Name*

        That’s great for you, but I think this guy needs really specific guidelines. I wear jeans and fabric shoes to my job, but I always look put together because I spend a lot of time selecting my clothing and I think I’m pretty good at it. This guy needs remedial help.

    2. BRR*

      I get what you’re saying and definitely agree that specifics are better than “dress less casual.” That seems maybe a little too much in the opposite direction though. This depends on the employee’s judgement though. My dad might need even more specific instructions.

      1. Clever Name*

        I think it’s pretty clear the employee doesn’t have great judgement with regards to dressing for work.

    3. Lissa*

      Yes! I am a remedial level dresser — I feel like no matter what i do, I just don’t look polished. In my job I don’t really have to, but if I have an interview or something, I will seriously just go to a midrange mall store that sells work-focused clothing and say “I have an interview tomorrow, dress me.”

      If somebody said to me “do better” when it came to clothes? I’d panic and feel badly, and still never feel quite like I got it right! I just have no sense for this sort of thing. When people talk about “not work appropriate” “that dress is good for a club but not a wedding” “afternoon makeup vs nighttime makeup” I can’t really make heads or tails of what specifically they mean.

      1. Temperance*

        Oh this is so easy to fix! I mean that as a compliment. You have good sense to ask the pros for help, so you’re already halfway there. I wear a lot of dresses because they’re easy. I don’t accessorize (unless you count a FitBit … lol).

        The woman who went to the media to complain how ladies were mean to her at a wedding is a great example of what not to wear; her dress was far too short and tight for a wedding, especially a daytime wedding. If you can see the direct outline of someone’s body in what she’s wearing, it’s probably not wedding appropriate.

        1. C Average*

          Ohhhh, that dress!

          I think she knew what she was doing, though. She wanted attention. And she got it.

          1. Temperance*

            Yep. Otherwise she wouldn’t have worn a bodycon dress to a wedding and then hit up the media.

      2. Bob Barker*

        I think it’s much more complicated for a woman in an office setting: there’s the hair and the face and the shoes and the cut of each piece and how it fits the body and how they all look together — compared to the male OP, who is basically wearing a khaki toga and still kinda getting away with it. So there’s remedial and then there’s remedial.

        If someone told you, “Psst, hey, spiff it up a little” you’d have a general sense of what’s meant, right? Obviously, because you know that a job interview is a moment when you need to spiff it up a little, without even being told, and you know to ask for help. Being only so-so on how to do it yourself is not so bad.

        (My mid-career self-spiffing innovation is dry-clean pants. That crease at the front of the leg, it looks spiffy! And I can afford dry-cleaning now.)

  8. Katie F*

    Tucked-in shirts are the worst, most uncomfortable way of dressing. One great aspect of my casual dress code at work is never having to wear a tucked-in shirt ever again.

    1. RVA Cat*

      A possible solution would be for him to keep a neutral blazer at the office and put it on when he’s interacting with the higher-ups. That would make the tuck or untuck issue irrelevant.

      1. Katie F*

        Yeah, agreed. I’m a big fan of “bring a class-up-the-outfit piece to work for use when interacting with clients”. I’ve been known to pack a blazer just for our monthly client meetings that I never wear otherwise.

    2. Triangle Pose*

      I am totally the opposite! I’m petite and so shirts or blouses tucking into ankle pants or pencil skirts or suiting look SO MUCH BETTER. Anytime I pull the hem out I feel like the entire outfit is lost.

    3. INTP*

      The OP isn’t even saying that he has to tuck in his shirt, though. She’s saying that his clothing is too big for him, in poor condition, and is worn untucked and with borderline-inappropriate shoes. If you want to wear your shirt untucked, it seems that it’s acceptable in the OP’s office as long as you take other steps to make sure that you are still presenting an overall polished vibe. I don’t think it’s unreasonable to expect people that want to wear their shirts untucked to pay extra attention to their clothing being well-fitted and in good condition.

      1. Trisha*

        OP here – INTP is correct. I would likely not even notice an untucked, neat shirt. I wear them myself on a dress down day — I’m a woman, so the untucked polo is shorter with a neat hem. When your shirt goes halfway to your knees, if you are not a woman, it just doesn’t look put together. I really, really do not care at all as long as the person looks neat and professional. My boss is more traditional and may find fault more, and I am trying to protect my employee from him, AND help his first impression with the rest of the organization.

    4. Temperance*

      I hate them, too. They don’t look right for women unless they are thin and small-breasted.

      1. The IT Manager*

        LOL! I really can’t imagine that that stock photo was not taken in 50s or 60s. There just no way.

        1. Joseph*

          I’ll bet at least half of the people who view that post have never personally seen a typewriter in use at an office.

          Computers became common replacements for typewriters in workplaces in what? Mid-90’s or so? Which would mean about age 40 or so is a ballpark cutoff for “actually worked with a typewriter”…plus NYMag readers likely skew younger…Yeah, it’s definitely more than half.

          1. zora.dee*

            I had a typewriter in an office in about 2002-2005. It was kind of an old-school office with a lot of old forms still in use, and there were certain things that “just had to be typed in” manually. Meaning, there probably was a better way to do it, but the older bosses just wanted it done that way because they always had.

            People’s minds were blown the first time I showed them how to print one addressed envelope at a time on their printer. Minds. Blown.

          2. Ellie H.*

            We actually had a typewriter in my office in early 2012 that got occasional use for typing forms. The woman who used it regularly (nobody else did, it was behind her cubicle area) had been in the workforce a long time (much of it typewriter era, obviously) and retired that year and the typewriter went away when we moved the office upstairs. But it really got used for a work purpose! It was the kind of situation where you COULD hand write in on these forms if you wanted to though. ;)

          3. Bob Barker*

            My office kept an electric typewriter till about 2002 or 2003, for typing envelopes and for no other task at all. Then I guess we got nicer printers, because I know printers have been able to do envelopes since well before that year. The typewriter went the way of the dodo, and now if anyone needs a small one-off item, that’s what a label printer (hooked to a computer) is for.

  9. BadPlanning*

    Is this person somewhat freshly out of college? I think when you go from college to a relatively casual work place, it’s easy to keep wearing your college things and think it is close enough (and sometimes is, I’m sure). Like, we have to wear kakhis? Check, I have these pants my mom bought for my freshman year and I wore them for all my dressy events in college.

    My workplace is t shirts and jeans casual and a lot of the recent hires still have their college t shirts in heavy rotation. Not just the official college logo — but the assortment of t shirts you get for assorted activities and parties. It’s not bad necessarily, but I confess sometimes I wonder when they’ll buy their adult wardrobe. Then part of me dies inside and misses all my college tees.

    This is a long winded way to say that the employee may really need it pointed out that while they’re meeting the technicality of the dress code and they need to dial it up a few notches.

    1. Megs*

      We have a giant pile of (almost entirely black) college t-shirts in a closet that I’ve been meaning to hire someone to turn into a quilt or throw pillows or something. My husband in particular has a ton of shirts that he will almost certainly never be able – physically or professionally – to wear again, but could never bear to part with.

      1. AnotherAlison*

        My husband has his high school senior class t-shirt hanging in his closet. He graduated in 1995.

        I’m not generally sentimental, but I do have a 2003 8k race t-shirt still in regular pajama rotation. The sleeves are frayed, the graphics are cracked, but it still gets the job done.

        1. Megs*

          Yeah, I’ve got a t-shirt like that, only it’s a Babylon 5 shirt I got at a convention in 1997-ish.

          1. Megs*

            Annnnnnd I just realized B5 first aired over 20 years ago. If you need me, I’ll be rocking in the corner contemplating my own mortality.

            1. The Cosmic Avenger*

              I refuse! We’ve still got a whole new generation that we need to introduce to B5!!

              (I’m working on it…already had the minion want to watch Firefly through multiple times. Which reminds me, if it pans out this might be the minion’s first year for Can’t Stop the Serenity!)

              1. Megs*

                Nice! My spouse and I just finished watching Farscape (which I’d never seen) and are about to start B5 (which he hasn’t seen since it aired). I’m not sure what we’d do if our future child wasn’t a nerd.

            2. Wendelenn*

              I’ve just started a re-watch! one episode per night. “What do you want, you moon-faced assassin of joy?”

          2. Hlyssande*

            I still wear a tshirt I stole from my older brother in the late 90s. In public! It’s only faded a little and the lettering is still good! There maybe one tiny hole! It’s one of my favorites.

            But I would never wear it to work.

        2. many bells down*

          Mr. Bells has several Nine Inch Nails t-shirts that are at LEAST 20 years old. Older than our children. And oddly, only 2 of them have become unwearable. I plan to make them into throw pillows, like Megs said. ;)

          1. AnotherAlison*

            My husband stole my 90s concert tees and wore them to work, ruining them all since he was a mechanic. (This was back when all concert shirts were XL only.) But HIS concert shirts are perfectly preserved. I should just grab his Korn shirt and wear it to the gym one of these days.

            1. KR*

              !!!!!!! What!!!!!!

              I have a 1980-something Pink Floyd concert t-shirt that I have from my mom. I guard that thing with my soul. I don’t even wear it out in the sun because I don’t want it to get sun-bleached. The last time I remember wearing it was when I took my license test 8ish years ago. I hate to wear it because I don’t want to put it through the wash.

            2. Rusty Shackelford*

              (This was back when all concert shirts were XL only.)

              Huh? That was a thing? Not at the concerts I went to (80s/90s).

        3. cercis*

          I have my senior class T too – from 1991. And I have a jean jacket I wear regularly that was from xmas 1982 or 1983 (my brother’s). I also realized that my backpack purse was bought in August of 1995 (and is still in great condition) and a couple of dresses I wear as swimsuit coverups came from Walmart in April of 1993.

          I might have a small hoarding problem. However, with the exception of the jean jacket, all these are in near mint condition. Only the backpack purse gets regular exposure, the tshirt will never be worn and the swimsuit coverups are strictly coverups at the pool or a swimming hole. The jean jacket looks like all the ones for sale in the mall – by which I mean it has frayed hems and some small holes and is very light blue. When it was new it was very dark blue.

        4. BananaPants*

          My husband and I both have our high school letter jackets hanging in our hall closet. He graduated in ’97, I graduated in ’99 (same high school, we didn’t date then, long story). Neither of us will ever wear them again but we can’t bear to part with them.

      2. Bulbosaur*

        Ha, we have a T-shirt Archive in my house. One of those big Rubbermaid tubs full of band T-shirts from the ’90s and early ’00s.

    2. A. Nonymous*

      “Then part of me dies inside and misses all my college tees.”

      Get your tees if you like them! There’s no age limit on wearing teeshirts, I promise.

      I really hate the idea of an “adult” wardrobe, to be honest. If you are allowed to within your dress code and you LIKE what you wear what’s the big deal of never “updating”? I mean, I have some nice dresses to wear if I’m going to an arts event or something that calls for it, but I’m just not a fan of the Business Casual Uniform(tm).

      1. AnotherAlison*

        I only have an adult wardrobe for work. I just don’t do a lot of other things that require “adult” clothes. Most of the time it’s fine, but last weekend we went to a bingo event for a friend who has terminal cancer, and I wore shorts, a plain solid t-shirt, and Converses. Apparently, white jeans, cork wedges, and a silky top would have been more appropo. That seems to be the suburban mom uniform. I’m a permanent college student instead. But, you know, who cares what outfit I have on when someone is dying?

        1. many bells down*

          I keep failing at having a job that actually requires adult clothes. I’m currently not only allowed but *encouraged* to wear Star Trek t-shirts to work. I’d actually like to dress up more!

        2. aebhel*

          This is me, too. My workplace is business casual, but in my own time I’m strictly jeans, boots, and geeky t-shirts.

        3. Temperance*

          The mom uniform where I live is yoga pants, a baseball cap, and a sweater tied around your shoulders. lol.

      2. Bowserkitty*

        Agreed. Late 20s with several cartoony shirts. (Who doesn’t want to wear Tina Belcher’s face on their torso!?)

      3. themmases*

        Yeah, I went t-shirt free for a while when I was in my first job. But it’s sad! Once I started buying them again, the floodgates opened and I couldn’t get enough.

        I have some from Uniqlo that are lovely and not childish looking at all. Most aren’t my thing, but Threadless has some great minimalist ones as well.

    3. always anon*

      If t-shirts are part of the workplace, then I think they can be considered an “adult wardrobe” as long as they’re not displaying anything offensive or insappropriate. I really hate that term because it sort of implies that everyone has to get away from fun clothes once they get older.

      You will pry my #yayhamlet t-shirt from my cold, dead hands. I will wear that until someone tells me it’s not okay for the office.

      1. Kyrielle*

        Yeah, I’m not giving up “Never Trust an Atom, They Make Up Everything” shirt until the writing peels noticeably. And I may have to replace it then.

        1. Crystal Vu*

          I have that shirt too! And I’ve gotten a few comments from others just wearing it out and about.

    4. Nervous Accountant*

      Oh, the adult wardrobe conversation reminds me of a link I read last night, one of those listicles.. “24 items women over 30 shouldn’t wear/own” and it made me cringe so so so bad, like ewww wiht all the judgy mcjudginess.

  10. Cambridge Comma*

    I’m quite often guilty of missing the point where a work-acceptable item of clothing when new (in my v casual office) becomes non-acceptable owing to fading and fraying. Possibly because I don’t have a full length mirror at home, or it might just be denial.

  11. The IT Manager*

    I’m just going to note that if I had to pick one thing to fix first it would be the frayed hems. Sounds like he needs to fix several things including buying a wardrobe the right size so everything is not baggy. Given what the LW said about him being very unlikely to be having money problems, it sounds like he’s just lazy about shopping continuing the wear old, worn out, and ill fitting clothes. Don’t piecemeal the advice, though. You don’t want him to go out and buy new pant (fixing the hem problem) but they’re still so baggy that he looks sloppy.

    1. Mononymous*

      This is my husband. He hates shopping so much that he’ll keep wearing shirts with holes in them or nasty, ratty socks and shoes until I point-blank direct him to go to the store NOW and don’t come back without (whatever items he needs to replace). He’ll also keep wearing stuff that no longer fits, no matter how uncomfortable, until similarly ordered to shop. I’m guessing LW’s employee may not have someone at home to encourage a change, so hopefully LW can get through to him.

      1. KR*

        Ugh this is my problem. I was looking in my closet for something to wear the other day and both of my black cardigans were in the wash. Everything in my closet was unprofessional/something I would wear to school/ratty/didn’t fit right/ect. So before work I went to target and made myself buy two cardigans because I knew I wouldn’t go buy something if I waited. They weren’t on sale, but that’s my penance for waiting until I literally didn’t have anything else to wear to work.

      2. Temperance*

        I know this is probably unpopular, but I occasionally just buy stuff for Booth. I hate seeing him in the same 3 outfits.

    2. INTP*

      Agree that not piecemealing the advice is very important. I’m guessing this person just lacks a sense of detail and norms regarding clothing, since it seems like he isn’t sloppy about following the dress code or wearing items that conform to what his coworkers wear on paper. I think vague criticism like “You need to have a neater and more polished overall appearance” are likely to go right over his head, and he’ll have no idea what to do with it. He needs concrete action items, preferably delivered all at once. If you piecemeal it, he will follow the one or two tips you give him, but still overall look sloppy, and the ten follow up conversations will make him feel embarrassed and like he can’t do anything right. Better to have one very uncomfortable but straightforward conversation..

  12. Kimberlee, Esq*

    The thing that bothers me about this question (that maybe OP can address by running it up the flagpole?) is that this person is supposedly ruining their professional reputation by *following the dress code.* It’s fundamentally unfair. You either care about the specifics of how people dress, or you don’t, but don’t let employees think it is one way when, really, it’s another. We don’t have a dress code at my work, and I dress in a way that is comfortable for me but very dressed-down compared to some of my co-workers. Short skirts and off-shoulder tops are common, as are jeans and tees. They made a decision, as a company, to be cool with that. I love it, and if I learned that higher-ups were skipping me over for promotion because of it then I would very much think the problem was on them, and not me.

    1. Ask a Manager* Post author

      Eh, but dress codes usually have some degree of expectation that you’ll have a reasonably polished appearance. Even if that’s not explicitly spelled out, it’s usually understood to be the spirt of the expectation, and I’d hate to move to a system where every single expectation needed to be enshrined in policy. And in this case, he’s not in trouble for not following that expectation, but his manager is going to talk to him about it and lay it out more clearly.

    2. Koko*

      It’s only unfair if they judge him negatively for it and don’t tell him or give him an opportunity to make an adjustment. He’s not being penalized for following the dress code. He just needs additional guidance on how to apply it. A lot of things that affect how you’re perceived in your office aren’t written down or codified in policy anywhere. A good manager will give you a heads-up about those things.

    3. Anna*

      To be honest, whenever someone writing in says something is “ruining their reputation” I always have to take a moment to really weigh whether or not the OP is being a leeeetle bit overly dramatic. In this specific case, though, the person who can thumbs up or down a promotion or a special project is annoyed so it’s worth shining up just a little even if he is within the dress code parameters.

    4. INTP*

      I get what you’re saying, but at the same time, this guy is pushing the limit on multiple dress code things – his shoes are borderline inappropriate, his clothing doesn’t fit, his shirt is untucked, his clothing is wearing out, etc. To keep any single individual from being able to look like a slob while technically following the dress code, you would have to make the dress code restrictive in a way that would be burdensome and unnecessary to the majority of the employees. A dress code is not a substitute for social norms about appearance, it’s still going to be possible for someone to look inappropriate unless you have a draconian dress code that regulates every aspect of an employee’s grooming with no leeway for one or two casual allowances. They just need to talk to him about it.

    5. Temperance*

      You can follow the dress code in spirit while still pushing the envelope. Most reasonable adults wouldn’t show up to work in ill-fitting, worn, and frayed clothing, so I wouldn’t think to put it in the dress code that you need to wear clothes in decent shape.

      He’s damaging his own reputation by dressing like a total schlub. Booth works at a place that didn’t have to implement a dress code until the guy we all refer to as Captain Sweatpants was hired. He regularly shows up in sweat shorts, stained clothing, etc. … and he’s a well-compensated professional. Because of Captain Sweatpants, they now have an official dress code.

    6. Camellia*

      Our dress code says something like clean, neat, and in good repair. Sloppy and frayed could be easily addressed with this.

    7. Interviewer*

      I had a coworker who pushed the envelope on dress code at a law firm. She used to wear these pantsuits that looked like errand-running clothes for senior citizens in the 1990s. Like, we’re all wearing traditional conservative business dress clothing – suits, slacks, blouses, blazers, cardigans, skirts – and she’s in purple velour pants and matching hooded jacket. I think it said “pants suit” in the handbook, but didn’t specify what kind of material – so she bought several different colors and wore them every day. She was a few months away from retirement and limping toward the finish line. Her boss studiously avoided having the conversation, too.

      We eventually got to have Casual Fridays (no jeans, though), and we used to joke about what in the world she might wear. Like, if she got any more casual, she’d be in a housecoat and slippers.

      1. Aubergine Dreams*

        I gotta say, when I’m nearing retirement, I probably won’t care about the dress code either! Comfy pants all the way!

      2. Bob Barker*

        I have nothing but kudos for the huevos of your ex-coworker (not so much kudos for the making-it-difficult-for-everyone-else). Why am I not surprised that a legal professional of all people would be very effective at rules-lawyering a dress code.

    8. C Average*

      I also wonder if he wants to advance. I’ve worked with quite a few people (mostly IT) like this guy. They’re good at their jobs and enjoy what they do. They’re not interested in climbing the corporate ladder, and they’re resistant to what they regard as being fake in order to advance. They want to show up, do a good job, look the way they’re used to looking, and go home. If you remarked that their lack of style was holding them back, they might just look at you blankly and say, “From what?”

      1. annejumps*

        I was going to say, some IT folks take it as a point of pride that they don’t have to adhere to appearance norms.

  13. Noelle*

    How about when your boss, who is also the HR Manager, wears flip flops and ripped jeans in a business casual environment? Of course I wouldn’t say anything, but we already have a problem with managers taking HR seriously. I can’t imagine the way she dresses helps anything.

  14. Bee Eye LL*

    I manage an IT group who does everything from phone based support to running cables through attics to add new network drops for people. Most days we don’t even break a sweat, others we come out filthy dirty. For that reason, we are allowed to wears jeans and t-shirts because I want my group to come to work to WORK. It’s not like we’re giving presentations. Plus in the 100+ degree southern heat, having to move equipment around outside will leave you soaked after only a couple of minutes.

    1. Bulbosaur*

      I used to work at a big bookseller that required us to wear business casual even though more often than not we were crawling around on a filthy floor, cleaning up a truly disgusting bathroom mess or stirring up so much dust that your hands would turn black. It was godawful annoying ruining expensive clothes in that joint, all in the name of giving customers an ‘upscale retail’ experience.

      1. Koko*

        Flashing back to my college job at a dog kennel where the required uniform was white sneakers, white/off-white/beige khakis, and a white T-shirt with the kennel’s logo on it. We were provided two t-shirts. I had to do laundry CONSTANTLY because you better believe I came home covered in dirt and dog poo just about every day.

        All white outfits. In a dog kennel. I mean…

        1. Libby*

          Ew! When I worked at a dog kennel, they really didn’t care what we wore. A lot of the time, I got to work and put on one of the scrub tops that they kept around for the vet half, because I was so covered in hair and poo by the end of the day.

      2. Emelle*

        I worked at a daycare that didn’t allow jeans. Paint doesn’t come out of khaki pants as easily as one would think. I ruined so many pairs of pants… and no sneakers except less (brand specific) no print on a T-shirt. (And near review time, you dare not wear that striped shirt that you weren’t sure if it was striped with thread or printed, because that would come up in reviews.) Oh and don’t forget, you need to be on the floor as much as possible with the kids.

    2. A Non E. Mouse*

      Same here; we are allowed to wear jeans and “collared” shirts; my uniform as the only gal on the team is jeans, company-labeled polo shirt (untucked, though thankfully the “women’s cut” shirts are usually designed to remain untucked) and cute flats. I keep sneakers/socks in my desk drawer in case things get real. I will get dirty at least once a week, but there’s no telling which day it will happen!

      If I need to “dress up” I just make sure it’s my nice(r) jeans, and I take care to wear earrings that day. I don’t wear makeup, and my only jewelry each day is a wedding ring, so the earrings are like a fabulous little life hack for me. I keep some in my pen drawer too in case of emergencies!

  15. Yamikuronue*

    When I first started working desk jobs right out of college, I realized I needed a completely new wardrobe basically overnight to be compliant with dress code, and this was before I had my first paycheck. I bought 5 shirts and 3 pants from the Goodwill, and for a few months after that kept scouring Goodwill until I had a reasonably sized wardrobe. I am sure I looked just like this guy: Clothes that fit poorly, not tucked in (because I hate how I look with tucked-in shirts), sometime fraying or faded a bit because they were secondhand, often wrinkled because my husband did the laundry and just plain forgot to iron. Little things like that. I wonder if this guy’s in a similar boat? Back then, I would have been embarrassed as hell, but also appreciated the pointers on how to make the best of what I had without buying all-new clothes — ironing and tucking in (despite how much I hate that look) can really go a long way without costing anything.

    Now that I have my feet under me more, I can buy tailored shirts that fit me right and are designed not to be tucked in and still look professional. I’ve even figured out what to do with my hair :D People from that first job probably wouldn’t recognize me today.

  16. sam*

    Our dress code is “informal” (it’s driven very much by what group you work in – my group is actually pretty formal because we work in/near the executive suite) but the overall organization does have some basic rules in our handbook. these include the following:

    “At a minimum, clothing must be neat, clean and well-fitting.”

    Also, in addition to being prohibited from wearing athletic clothes or halter tops (I know, we’re monsters), we are prohibited from wearing anything “torn” or “cut-off”.

    I feel like these are the most basic, how to function in a workplace rules there could be, and this guy doesn’t sound like he’s meeting at least some of them.

  17. chocoholic*

    I love to iron and fold laundry! Those are about the only household chores that get done regularly. I take it a step down from my 94yo grandmother who irons her sheets though.

    I wonder if I could make a living, taking in laundry for other people :) That would be AWESOME!

    1. A. Nonymous*

      I would happily trade dusting and sweeping for folding and ironing! WORK TRADE PROGRAM

      1. Grapey*

        This works with me and my husband! I do ALL the cloth related cleaning for the house (clothes, curtains, towels, rugs and beds) and he ‘deals’ with the cat care, which is feedings and medications as well as bringing them to the vet. I’ll fold all day as long as I don’t need to touch a litterbox!

    2. Anonyby*

      My grandma did ironing for others for extra cash while my mom and uncle were in school. She was rather proud of it!

    3. Ellie H.*

      I have ironed my sheets before. . . I went through kind of a phase of it. I literally had to force myself to stop because it was becoming compulsive and making me crazy!

  18. Christopher Tracy*

    People from that first job probably wouldn’t recognize me today.

    Same here. Hell, I’m barely recognizable these days to people who met me when I started at my current company almost three years ago. I was not making enough when I started to dress how I wanted to, and now I can so I’ve had quite the Extreme Makeover experience (minus the surgery).

  19. Michele H.*

    If the employee is a general slob, then just putting him into a new pair of khakis and a new polo shirt may not do much good. And a neat, well-put together person can look great even in an untucked polo and khakis. It’s a difficult conversation to have, but you might have to say that a little bit more is expected from him since he works with the public. He needs to make a personal effort in selecting and caring for his clothes at home. I know a lot of guys with good salaries who live alone and do not spend one extra ounce of effort in taking care of anything–in the house, laundry, cooking. They come home from work, or the bar after work, and get on their computers until bedtime then wake up and pull a rumpled shirt out of a basket. I’m guessing mom did EVERYTHING for them except ever once saying, “Listen, young man, I think it’s time you learn how to put a knit polo on a hanger.” Now these guys are our co-workers. If the dress code states “neat, professional attire” then he has violated it, unlike the others, who may wear the same thing, but wear “neat” attire.

    1. Lurker*

      You’ve just described my other half. Drives me nuts how few life skills he’s managed to acquire in 50 years on this planet, and yes, he’s that guy at work when it comes to dress code. I’ve managed to weed out the worst of the early 90s Polo shirts from his closet, but he still leaves for work looking like he slept in his clothes as often as not.

  20. A. Nonymous*

    Has the employee recently lost a lot of weight? I know that if people’s weights fluctuate, even if they do have means, they may not prioritize a work uniform over clothing that suits them better personally. Plus, depending on the reason for weight loss, they may not be doing very well and frayed hems are the least of their worries?

  21. CQ*

    I had a similar question I was considering writing to you about, Alison, but perhaps it’s okay if I just air it out here? I work as a barista in large American-founded international coffee chain in Europe (it’s likely the first large coffee chain you think of). We’re generally required to keep up with a rather strict dress-code, but our store manager has been very lax because clothing is very expensive where we live, and she cares more that we treat the customers nicely than that we’re wearing all-black shoes or jet-black pants. The problem is, management is changing, and we’ve been warned that they’ll become more strict about the dress code.

    I don’t have anything against following the dress code, but I have to work with what I have. I make less than the poverty line and my visa status does not currently allow me to work more hours, so I have to make due with the income I have, which is already a really big struggle. I’ve been wearing the blackish pants I already own (very dark gray) and black sneakers (it’s important to have shows we can comfortably walk in), but they have pink accents on them, which are against the dress code.

    I’m really not sure what to do… push my luck by wearing what I’ve always worn, and plea poverty if the new management reprimands me for it, see what happens then?

    Has anyone else here ever faced a similar situation?

    1. A. Nonymous*

      My roomates did a clothing “share” when we were poverty level. They’d pool in and get like, 2 pairs of slacks and a shirt that they’d then share. It worked great for them, but they did go thru clothes quickly. If thrift stores aren’t an option then maybe you could look to see if there are any places in the area like “dress for success”.

      That sucks so hard, I really feel you.

      1. CQ*

        Thank you. A problem with clothes-sharing here is that I live in a country where people tend to be rather skinny, and I’m a full-figured gal with a very large breast size. Thrift stores aren’t so in vogue here either… it doesn’t fit to the culture, I guess. At least where I live, people tend towards spending more for high quality, but people tend to also have higher incomes. For me, if I buy new work pants and shoes to accommodate this dress code, it means taking money out of my budget from something else, and since every other line my budget is a fixed, necessary bill, it would have to come out of my grocery budget, which is already ridiculously tight.

        But that is a really nice idea if you live with people who are similarly sized. I used to share shoes with my mother when I was living in my home country.

        1. Observer*

          Can you paint over the pink accents on your sneakers? And phase in the other changes slowly over time, starting with the most noticeable items?

        2. MommaCat*

          With the shoes, you could see if a sharpie would cover those pink accents. I had to do that a couple times for theater.

    2. Kyrielle*

      I hate to suggest it, but maybe a permanent black marker or some black shoe polish to the sneakers’ pink accents? That seems a shame to do, but if it worked, probably cheaper than new shoes.

    3. irritable vowel*

      Get a black permanent marker and color in the pink accents? You could also dye the pants true black if dark gray isn’t good enough for the new management – a box of clothes dye is pretty cheap.

    4. MayravB*

      Can you dye the pants black? I’ve dyed clothes a darker version of what they are already (jeans to a darker navy), and honestly, it’s not nearly as mysterious and hard as people may think. For Rit brand dye, you fill a bucket with hot water, dissolve in the dye packet and some salt, throw the pants in and stir, then leave it, smooshing it around occasionally, then rinse and dry. There are also dyes that work in a washing machine. The dye was around 7 bucks (in Canada). For shoes, I’ve definitely coloured in worn spots with permanent maker, in a pinch.

      1. CQ*

        Wow, those are some really great ideas. Thank you! I did think about switching out the pink shoelaces for black ones (which I already own), and I thought of covering the pink parts with duck-tape and coloring it in. I didn’t think about dying my gray pants, so thank you for that suggestion.

        I honestly feel shaken down by my employer for having to buy new shoes on my limited income. It feels so disingenuous to smile while I take peoples’ money for four- and five-dollar coffees, and then to have to deface my own property just to be allowed to work.

        1. KR*

          It’s hard to swallow, but it’s a really common thing in the working world. I hate to say it like that.

        2. MayravB*

          Yeah, that’s got to feel really lowering :( I wonder if there’s some way you could reversibly cover your shoes. Shoes are so expensive, it’s a shame to colour them in, especially if actually like the pink part! Tape over rubber/plastic should be reversible, because you can scrub the gummy residue off after, but I think duct tape over cloth/mesh would be really hard to reverse. I advise a Pinterest search :)

    5. C Average*

      I used to work for that chain. I was similarly broke. I actually took to wearing a black knit shirtwaist dress with tights and black Mary Janes, rather than wearing separates. I found these items at a secondhand store and then scoured MORE secondhand stores until I found more just like them. They were pretty easy to find because they’re such classic pieces that they’re never really IN style and also never really OUT of style. Because it was one piece, I didn’t have to worry about keeping things tucked in. I looked very dressy, which my managers appreciated, and I was also very comfortable.

      Like many others who have chimed in here, I’m short, short-waisted, and busty, and I look SO dowdy with my shirt tucked in. It makes me terribly self-conscious and uncomfortable. I actually feel noticeably dumber when I’m wearing anything with a belt, and I believe this is because so much of my attention is focused on feeling unattractive and counting down the hours until I can get out of the infernal belt and into something comfortable and flattering. A tucked-in shirt would be just about a deal-breaker for me.

      1. Christopher Tracy*

        I’m short, short-waisted, and busty, and I look SO dowdy with my shirt tucked in.

        Right there with you. I will never tuck in my shirts. That’s another reason I wear dresses 24/7 at work.

      2. CQ*

        I wear a try to wear a dress with tights and black ballet flats in the winter, but it’s a bit too warm for that in the summer. I can’t wait till I’m done with my graduate degree next year, then I can quit slaving away for corporate coffee and get a job in my field – and wear what I want! (within reason of course because that’s what started this whole thread)

  22. ModernWizard*

    Long-time reader, first-time commenter. I’ve been on the receiving end of “Dress less casually and more professionally” conversation. My supervisors made this request of me, adding some helpful specifics.

    Besides giving examples of things that they would prefer me not to wear, they also gave me examples of times when my outfit met the dress code. Also, after that initial conversation, they pointed out once or twice that the outfit I was wearing was appropriate. Thus I knew that I was heading in the right direction.

    They pointed out one person who was following dress code. They said that they did not expect me to copy that person’s style, but to pay attention to the tailoring and cut of her clothes, as well as shoes.

    I don’t think anyone likes to be told to change what they wear, but a friendly approach, coupled with concrete references, will make the notification much easier.

    1. Camellia*

      Concrete examples and suggestions! This is fantastic, wish all managers could/would do this.

  23. A Girl is No One*

    If there are specific things, they should be in a dress code. As an example, ours has: no baggy pants, no shorts, no holes, no frayed hems. They will send you home for any of these things. A woman showed up in expensive designer jeans that were “distressed” and had one hole near the knee. She was sent home to change.

    1. Ask a Manager* Post author

      I don’t know, I don’t think you should have to spell out every possible thing that could violate the dress code, and that it can be kind of infantilizing to do that. It’s reasonable to expect that people will generally understand what “professional appearance” means, and then if someone doesn’t, you can just talk to them about it.

      1. A Girl is No One*

        While I get what you are saying, I’ve never worked anywhere that did not have a dress code, sometimes formally written, sometimes orally passed. In my current job, we teach the kids-who-got-kicked-out-of-your-kids’-school, and the teachers are unionized employees, so of course we have a written code. Holes in jeans/baggies/certain colors can mean very particular things to the kids we teach.

        I think it’s at least as infantilizing to have content monitoring software, email logging, or time sheet audits. All those are very common as well, right?

          1. A Girl is No One*

            If only we could return to a simpler, more genteel existence…ah I long for the good old days of Mosaic, dial-up connections, and rec.arts


      2. michael snow*

        I strongly disagree

        I’m a 50+ y/o man, working in a professional environment (freelance project management) and only recently discovered (via an abrasive friend of a friend) that my clothes look “awful, just awful”

        My (female) friends ‘defended’ me with comments like “Oh, he always dresses like that” and “You’ll get used to it” and “That’s just how he is”

        1. michael snow*

          (Oops, pressed submit by mistake)

          As I’ve been wearing exactly the same for thirty odd years, just replacing things when they no longer fitted, or I noticed a stain or irreparable tear, that means I have look “awful, just awful” all my working life

          Many technical people DON’T genuinely understand what “professional appearance” means – and I include myself in that group

          I still do not know what makes my clothes (white cotton shirt, blue cotton trousers, black shoes & belt) “awful” and someone else’s acceptable

          1. Trisha*

            I don’t know what this person may mean by “awful”. Maybe your clothes are not clean, or are in disrepair?

            My employee has greatly improved as of late. He will never be a fashion icon, which is FINE! He is just wearing clothes that are clean and in a decent state of repair, and relatively neat. That is all we really need.

  24. Belle*

    I sometimes think that dress code also changes based on your generation/childhood expectations set.

    For example – I in my early 30s and the small town I grew up in, I never saw an adult in anything other than jeans and tennis shoes (including at mass on Saturday nights). It wasn’t until I moved to a bigger city and started my first office job that I learned about business, business casual and casual. Honestly, I still have trouble with “dressing for success.” I am short, pudgy and large chested with some feet issues, so I would much rather be in a t-shirt, jeans and tennis shoes to be comfortable. However, it took me several years to really come up with a look that comes across as professional and meets all of those requirements (and had some friends help me shop since I am still pretty clueless about clothes).

    I do still wear t-shirts, but they are plain and not wrinkled. I then put on a scarf or other jacket to help it out. But I can relate to the person who struggles with it — I probably always will!

    1. Ad Astra*

      I grew up in a poor family that also didn’t attend church (but if we had, it would have been one of those “wear what’s comfortable” churches), so we never really dressed up. I still struggle with this, and being a bit overweight my entire life has complicated it as well. I got very good at styling jeans and T-shirts in a way that flattered me, but I still flounder when it comes to business clothes. I always felt frumpy in my dress code-approved outfits, like I was following the letter of the law but couldn’t seem to hit the spirit of the law.

      For me, the solution ended up being finding a job where the dress code is casual.

      1. Kelly L.*

        I know for my part, I have…weird fears about something fitting in the morning and then being excruciatingly tight later in the day? It causes me to wear my clothes a little bigger than I need to, which when coupled with manufacturers putting spandex in everything so clothes “grow” during the day, leads to me looking like a pile of loose laundry by mid-afternoon.

        (I finally had an epiphany just.recently. about what experience caused this fear. It was almost 20 years ago. I was wearing a beautiful non-stretchy skirt in a size lower than I usually wore, and was really proud that I’d lost weight. And that I thought the outfit was totally cute. And I went to meet with my then-boyfriend, looking all cute, and somehow the day turned into interminable watching boring movies on his friend’s couch while eating pizza. The skirt felt like a waist-garrote, and I couldn’t leave without looking rude, or at least 19-year-old me thought I couldn’t, so there were like ten hours of this. And now I subconsciously try to avoid this at all costs. Remembering hasn’t fixed it yet, lol.)

        Anyway, tl;dr, but I think I *am* this employee! LOL.

        1. KR*

          I get bloated a lot because of a combination of stomach issues so I buy a little bigger too – I was bathing suit shopping for a 1 piece and the saleswoman tried to sell me on getting a size down, but thankfully I had the foresight to go shopping while I was bloated so I could plan for the food children and bloat children. (:

  25. Ad Astra*

    1. It’s interesting to hear this kind of question being posed about a male employee. I feel like I hear it more often with female employees, where there’s just so much gray area about what works and doesn’t work.

    2. Is this employee overweight or in some way larger/smaller than most people? My husband is a very big dude and has a really hard time finding stuff that fits properly. His pants tend to be too long and end up frayed at the end, and with shirts he has to choose between way too long or just a little too short (he usually chooses way too long). He also can’t get his dress shoes tied, which he hides under the too-long hem of his pants. We typically can’t afford much tailoring, so it can be a bit tough for him to look polished.

    However, my husband would look more polished if he ironed (or even thoroughly wrinkle released) his clothes, and it drives me nuts that he doesn’t. So even if some things can’t immediately be helped, certainly other things can be. And more than anything, it’s worth at least a conversation.

    1. KR*

      This – I’m really short and petite so I have a hard time finding clothing that fits me that I can afford that’s also professional and flattering. Most office pants and blazers make me look like a little girl trying on her mothers clothes or overly frumpy. I can’t just buy anything.

    2. Observer*

      Not all tailoring has to be expensive, and you can do some things yourself. Fixing shirts tends to be an issue. But, at least in NYC, many dry cleaners have a tailor on staff and can do things like let out the seat of a pair of pants for $10-15. Hemming is about $5-10, depending on what you are hemming. And, if that’s also out of budget, hemming pants and skirts (or anything with a straight bottom, really) is something you can generally do yourself, although I admit it’s a pain.

      1. Chinook*

        There is also something called “No Sew” which can be bought in craft stores that can be used with an iron. You just turn up the hem, put the no sew between the two pieces, iron and voila – they stick together.

        In a pinch, duct tape also works well to keep a hem in place as well (just don’t iron it on).

        1. Christopher Tracy*

          No sew looks terrible on certain thin fabrics though – you can see the hemline where you put the tape. I swore I would never do this again after ruining a cute pair of pants that were way too long (they look even worse with wear and after washing/drying).

    3. Trisha*

      OP here – No, this employee is not at all overweight. He may be underweight, it’s hard to tell. ;)

  26. Hillary*

    Years ago I worked somewhere that went really specific with the dress code. Some of it was normal (no spaghetti strap tops, no flip flops), but some of it was absurd. No leather pants, vests, blazers, or skirts. Women’s shoes could be open toed or open backed but not open toed and open backed. Men had to wear collared shirts under sweaters. No golf shirts unless you were golfing that day. And so on.

    1. Megs*

      I don’t necessarily disagree with those recommendations individually for a more “business” side of business casual office, but that sounds like a great example of what Alison’s been saying earlier in the thread about how being overly specific just comes off as infantilizing.

  27. C Average*

    I really think some people are just oblivious to nuance when it comes to stuff like this, and they take the dress code 100% literally.

    My stepdaughters are both in the school band, and they’re required to wear dress black for concerts.

    The older one intuitively understands that this means tailored pants or skirt, a clean and pressed top that has not been in contact with the cat, and polished shoes. I didn’t have to teach her this. She looked around at the other kids and figured out the right way and the wrong way to look.

    The younger one would, if not given specific guidance otherwise, wear the too-short yoga pants she often sleeps in and a pilled hand-me-down knit top with cat hair all over it and a pair of black Uggs. And if you said something, she’d say, “What? It’s all black.” And technically, she’d be right. She doesn’t notice what other people wear and she doesn’t care what she wears, so long as it’s comfortable and she’s not getting scolded for wearing it. She hates shopping. I buy all her clothes for her in the kids’ section at Target. She’s just started wearing women’s sizes, and I honestly don’t know how we’re going to dress her for middle school, which she’ll begin this fall.

    I had to do a before-and-after exercise with her to show her how much difference it makes when clothing is clean, pressed, and fits correctly. She will probably always need a lot of coaching in this area, though, and I could see her taking a dress code very literally like the guy in this letter.

    I almost think that dress codes need Goofus-and-Gallant style illustrations to make clear what exactly terms like “neat,” “clean,” “in good repair,” etc., actually mean.

  28. LAP*

    I like the direct approach you suggest and I don’t think the manager needs to be afraid of being offensive. My husband is in IT and I work pretty closely with those types. They are usually pretty difficult to offend and respond well to honesty.

  29. Argh!*

    I have a coworker who is miserly, a big believer in recycling, and judgmental of anyone who spends money on anything. She is also obsessed with detail, so she can dress like a lumberjack in her Goodwill outfits and get away with it. I want to smack her sometimes. She looks like a total slob and she’s not a sloppy employee at all. (I suspect a touch of Obsessive Compulsive Personality Disorder in her case, and I give her a wide berth)

  30. Ringless*

    Could it be that both employees dress equally well (and their clothes both fit fine), but the “slob” is overweight (or less conventionally attractive in some way) whereas the other employee is slim? Many people (consciously or subconsciously) automatically associate looking overweight with looking sloppy, especially if the overweight person is female, and it’s completely unfair to the employee if the “sloppiness” is not an issue he can simply fix with his clothing. No matter how figure-flattering clothing may be, it’s probably not reasonably to expect it to completely hide a person’s weight.

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