my boss keeps reminding me to dress up

A reader writes:

I am a 46-year-old professional woman working in the corporate offices of a manufacturing company. My boss is about my same age, male, and he works 3 states over and we rarely see each other. Our relationship is strained, but mostly professional.

About a year ago, I was asked to present information to the senior vice president of teapot making and his direct staff, a bunch of teapot-making vice presidents. I was to be in the room with them and my boss was to be on the phone from his remote location.

As we were discussing the presentation I was to give, my boss reminded me to “dress up” for the presentation. I was shocked, but took it as a one-time thing and even told some of my coworkers, who made a joke of reminding me to “look pretty” — always out of earshot of our boss.

Fast forward to a few months ago when I was to make a presentation to the same group. As we discussed my presentation, my boss, again, told me to “dress nice” for the presentation. I was shocked and said something like, “I know how to dress appropriately” or something like that.

But it is looming again. I am to present to the group again. And I want to prepare for my boss’ “dress nice” comment. I tried channeling my inner Alison, and thought of responding with “Waheed, this is the third time you’ve reminded me to dress up when I am presenting to upper management. Have there been concerns about my work attire?” Because, remember, I see him perhaps five days a year in person.

Would this be too confrontational? (I have been accused of being confrontational.) Would it get to the root of the problem? (I ask that because one of my other observations is that he never comments on my male colleagues’ clothing choices when they present in front of upper management. I am wondering if it is a gender bias issue. I have had other issues with him that can be tied to his bias against women in the workplace.)

So this might be a weird thing about me, but I actually wouldn’t be terribly bothered by these remarks. In fact, I’ve had bosses who reminded me and others to dress nicely for particular events, and I always just took it as a mildly useful reminder. That said, this was always in jobs where people weren’t normally in suits every day, so it didn’t seem crazy to be reminded when an event called for something more than our usual level of formality. But even if I would have figured it out on my own, it’s never bothered me terribly to hear it.

But I wonder if this is about something more. You mention that you’ve had other issues with him, and that you’ve seen gender bias in him. Against that backdrop, I can see why this comment might come across differently. And if you’re sure that he’s only saying it to women and not to men, that’s understandably going to be more of A Thing. (But for what it’s worth, it sounds like he’s making these comments to you on phone calls, and he could presumably be saying things to others on his phone calls with them that you wouldn’t hear.)

Anyway, the next time he makes one of these remarks, I don’t think there’s anything wrong with saying, “Out of curiosity, have you ever had concerns about how I dress? You’ve reminded me to dress up a few times and it made me wonder.”

But I wouldn’t worry about it too much beyond that, and in general I’d try to move away from finding the remark shocking. I really don’t think it is, although the sexism issues you’re spotting certainly are cause for alarm — but that’s a separate thing.

{ 135 comments… read them below }

  1. Hephinstine*

    I’m afraid this is one of those things where you roll your eyes (out of his sight) and move on. Annoying, maybe even obnoxious, but Not Worth It.

    1. Clever Name*

      Yeah. I’d treat it like parenting advice from strangers. “That’s a great idea, thanks!!!” And then do whatever you think is best regardless.

  2. Joey*

    The comments are coming across as insulting mostly because your relationship is already strained. You’re looking at the comments through that lens.

    1. Yet Another Allison*

      This is possible. It’s worth asking yourself if he is just clarifying that this is a formal dress kind of event.

    2. Queen Anon*

      No, I think it’s just insulting on its face. “Yes, I know you’re a professional and have been in the work force for decades but I don’t trust you to dress appropriately, so I’m reminding you – as if you’re 12 and I’m your mother.” Unless there have been dress-related issues prior, there’s no place for a comment like that in the workplace.

      I actually did have a boss make a comment like that to me once but I understood it and thought it was appropriate – it was a very low-key office and we all wore jeans every day, but one day I had to accompany him to court. I knew why he made the comment – he hadn’t seen me – or any of the support staff, for that matter – in professional office clothes in ages. I didn’t resent it at all, but if he’d made it out of the blue after seeing me in professional dress day in and day out, I would’ve found it uncalled for and insulting.

        1. My two cents...*

          ya never know… your boss might have had to deal with male reports that showed up to these types of presentations in whathaveyou that resulted in long ridiculous conversations about what ‘business attire’ actually means.

          should he say it? probably not. but you seem really riled up over a comment that has occurred *twice in the last 1-1.5 years*, and for a presentation where he will not physically be present. you’re representing him as well as yourself, and he’s simply trying to cya…even if he sounds archaic/outdated/good-ol’-boy.

      1. Joey*

        That might be baggage from your days as a kid. I hear it as “I’m super neroutic and for my own sake and sanity I need to know I reminded you to dress up even though I know you don’t need it.”

        1. AVP*

          That’s how I’m hearing it as well, possibly coupled with my own baggage of having a receptionist once wear a knee-length Wu Tang Clan t-shirt on a day that a major client was coming by.

          I also have a super neurotic boss and now he, or I, are responsible for warning people when we know we’re going to have visitors.

        2. Marisol*

          I got the same vibe. When you’re the boss, it’s your ass on the line, so I can’t blame someone for taking extra precautions.

  3. Dawn*

    I had a fabulous boss who used to make what I would always think of as “mom” comments- she’d say little stuff like “be sure to use a professional tone when sending that email” or “don’t forget to smile when you’re on the phone with the Teapot Handle Vendor” and it would DRIVE. ME. INSANE. However, she was just saying that stuff as a “just in case”- it wasn’t a reflection on my performance at all. She just wanted to be absolutely, totally clear what her expectations for situation X, Y, or Z was, even if it was so ridiculously obvious that of course I knew that’s what she wanted me to do. Her MO was just to make sure that I understood what she wanted from me in a given situation.

    Maybe your boss is not like my former boss, in which case that totally stinks. But, if he is just the type of person to drop “mom” comments, he’s not the first person to do so and definitely not the last!

    1. Snarkus Ariellius*

      And I find this type of feedback highly irritating.  What did she think you were going to do?  NOT be professional in an email?  NOT be nice to someone on the phone?

      I get that your boss felt she needed to do it, but it’s only necessary if you’re not doing it.  If you have to remind an employee to do the basics like that, either you’re a severe micro-manager or you shouldn’t have hired the person in the first place.

      Then again, I find that maternal nonsense in workplaces so condescending and infuriating.  I’m not a child, and I don’t need a mom or a dad.  In my case it was my ex-boss’s way of trying to be “closer” to me, but I always maintained we weren’t friends.  She was my boss.  Let’s act like it.

      This same ex-boss once criticized me for using the “wrong” set of doors.  Keep in mind, this was a large ballroom type of place and there were four sets of doors on the same wall.  She was up front, and she saw me enter the room.  When she said, “I wouldn’t have used the door.  You should have used the other door,” I gave her a head tilt and confused look, which meant to convey, “Did you really mean to say what you just said?”

      1. Lamington*

        I had a “mom” boss and some of her questions and actions were inappropiate. i don’t need advice or approval on my pets or boyfriend.

      2. Jen RO*

        Well… I have a bunch of new-to-the-workforce reports and sometimes they are *not* professional or nice enough and yes, they need to be told. They aren’t doing it on purpose, they are just new to writing corporate emails in English (their second language). I’d much rather they feel babied for a few days than have someone in another department pissed off at them for being rude.

        1. Ornery PR*

          ITA. I work in a customer service industry and I’ve overheard terrible unprofessionalism on the phone or seen it in email. But no one here is young or inexperienced. Since my role is in communication, I send out periodic reminders (like once a year) to tell people to be professional and that you represent the company in call communications, etc. I’ve notice the people who seem most annoyed at those memos are the ones who need to work on it the most.

    2. Revanche*

      Totally worked for someone like that who near-obsessively micromanaged certain things, and it wasn’t personal as I discovered when other former employees confided in me, it was more or less like a nervous tic for that person. I had developed a relatively easy relationship with that boss so I either pushed back or laughed it off with a side of “stop that” when appropriate. If I didn’t have a relaxed relationship with the person though, it would be very easy to take it as a reflection on my performance rather than their problem.

      And to be fair, there were times I realized that if the micromanagey reminders weren’t made, details would have been missed by a less experienced person.

      Though the “be nice” comments are also a personal thing: I don’t communicate the same way as that boss did so what I perceived as business like was perceived as cold by that person. It’s a matter of style in a lot of cases.

    3. Ashley*

      I supervise my company’s interns – they are a direct reflection on me and their performance is a big part of my annual review. I ALWAYS remind them to “dress appropriately” and “speak with confidence” prior to the end-of-program presentation they do in front of our officers. I hope they don’t feel as though I’m being their mom (I’m only a few years older than them myself!)…but, they’re 20-22 year olds, and our office is otherwise incredibly casual so I think (and hope!) the reminder is seen as a gentle one.

      1. VintageLydia USA*

        I think interns are different. Presumably they have very little or even no office experience and they’re there specifically to learn about that stuff.

      2. Katie*

        Interns are a different story. I think it’s perfectly fine to remind them to dress appropriately or speak with confidence. I always regret those moments when I didn’t remind them of minor things.

    4. Adam*

      I get the feeling if I were a manager I’d be exactly like your former boss. Not because I wouldn’t trust my staff necessarily, but because I’d have some extreme anxiety over worrying whether or not someone would get things done exactly the way I wanted them to unless I made absolutely sure of it or did it myself. If something did go wrong I’d more likely see it as a really bad failure on my part.

      People can rest easy; I’ve never had any desire to be in management.

      1. Jamie*

        Are you sure you’re not the former me? Because when I first started managing this was exactly my problem.

        If you ever want to make the jump rest assured it gets easier. Just focus on all the crap you’ll really be blamed for if it poops the bed and you stop worrying about the stuff no one will put in your lap. It just takes time…and some vodka. :)

        1. Adam*

          Maybe. Do you like to cook? And if so when company is over are they by no means allowed to assist with food prep WITHOUT YOUR EXACT DIRECTION?! Then we might indeed be spiritual twins.

          Actually I’m not that extreme about it, but if you’re helping me prepare there is a blue moon out, and it’s probably in my hand (beer joke).

          1. Jamie*

            Why, yes, I am a control freak in the kitchen, but that’s only because other people may mean well but clearly have no idea how to do anything correctly.

            But you like beer, so we’re apparently not the same person. But you’re enough like me that I wish you worked here – the world can use more of us.

            1. Adam*

              Rest assured, beer may be my usual go to, but I always keep a bottle of vodka on my drink shelf for when my Russian genes act up.

  4. TotesMaGoats*

    I would probably take a deep breath and move on. If things are already strained, I wouldn’t up the volume on something that could be innocuous. My former boss would randomly do this to me. We had a different relationship that yours and I would turn it back to her and ask which of the 4 matching suits we both owned she planned to wear so we wouldn’t match….because it happened more times than one.

  5. SJ*

    My previous job was a pretty business casual office in regards to attire. Whenever we had board members or potential donors etc. in our office our management staff was requested/required to dress more professionally in suits – even if was a Friday and the rest of the office was in jeans. I don’t think it’s a strange request since you’ll be in front of vice presidents and the senior vice president for your presentation.

    Maybe the silver lining is that you keep getting invited to these meetings to present. You must have some good presentation skills they find valuable!

    1. Ashley the Nonprofit Exec*

      I agree – we are pretty casual (not old-jeans-and-a-t-shirt, casual, but nice-jeans-nice-top casual). That is totally fine in the office day-to-day and I have MUCH better things to do than critique outfits (or insist that people spend their nonprofit salaries on clothes and dry cleaning they can’t afford). However, the rest of the world isn’t that casual, and sometimes staff speak to groups or go places where jeans will be wildly out of sync or even draw stares. I do sometimes say, “this is a dressier thing” – mostly because I’ve been to these events/meetings before, and I don’t want my staff to feel uncomfortable or out of place. The most common response I get is sincere thanks. It’s also common for people to ask about the dressiness of events/meetings. Dressing inappropriately does not make a good first impression, and nobody wants that for themselves or our organization. Granted, I’m a woman (who also prefers her jeans) talking to women.

      Maybe you’re taking it that way because you don’t like your boss, or it’s making you uncomfortable because he’s a man. Although I do have to say it’s a annoying that he’s giving you this same piece of information over and over about meeting with the same people. I’d be sure not to make too big a deal out of it – I doubt it something you should be taking personally. He might just think it’s a helpful hint.

      1. My two cents...*

        it’s only happened once over a year ago, and again a ‘few months ago’. OP is just bracing for a third ‘reminder’. it’s annoying, but once a year (or so) isn’t really ‘over and over again’.

      2. Alma*

        Perhaps the supervisor doesn’t mean what s/he is actually verbalizing… Not “dressier”, rather ” wear banker’s gray or dark navy suit with a tailored blouse”. OP, someone posted yesterday about the John Malloy “Dress for Success” twin test. Two photos of the same person in different outfits – the question is “Which twin is more successful?”

        Men don’t have a lot of options in a suit. Women do – the supervisor may be thinking that a dress, or a pastel suit with a peplum, or a shorter skirt, or silkier blouse is not the look s/he is trying to convey. I have no idea what business you are in, but I would take a lesson from what the supervisor wears. I also think I would choose my time and ask sincerely what exactly the supervisor is attempting to convey. It is a question I would ask if I wanted to be sure I was meeting my supervisor’s expectations.

        Just my “sense” of the question. I may be wayyyy off track.

    2. Elizabeth West*

      We have the same reminders. Normally it’s casual jeans Friday every day, but if clients are coming in, we’re asked to wear business casual. Lately, however, it’s only been required for those in meetings with those people, not the entire office. A ton of people work from home when we all have to wear BC.

  6. BadPlanning*

    This would be pretty normal at my job — but we have a super casual environment. Last time that I had to dress up, I had to buy a new pair of pants because I, erm, grew out of several of my dress pants (sigh).

    But in other environments, I could see how it would be annoying. I think tone would probably be important here. Is the boss asking with a vaguely creepy overtone? Or is it more of an inside joke sort of thing, something like, “It’s that time of year to dust off the dress clothes again! But I get to sit in my home office in jammies!” Or is it just casual — maybe he had people in the past were terrible at dressing up and now he feels like he at least has to do a blanket reminder (the one guy that ruined it for everyone).

    1. Addiez*

      I was going to say the same thing! Just very neutrally – thanks for the reminder, what particularly are you thinking of? I could see a situation where he wants you to be wearing a formal ballgown or three-piece suit and is disappointed every time you show up in a tux. It’d be good to get clarification.

  7. Lily in NYC*

    You really, really need to let this go, especially if you’ve been accused of being confrontational. And if you normally dress casually when you don’t have presentations, then maybe he’s just covering his bases. I know it’s annoying and feels paternalistic, but there’s a big chance saying something will just backfire.

  8. AnotherAlison*

    I think I could overlook the boss’s comments since the OP does not see him regularly and it’s a manufacturing business. I’m in a business casual office, and work with experienced (mostly male engineering) professionals, but we often have conversations about what we’re wearing to offsite client meetings before we go. I just came back from a meeting yesterday where the client culture is cowboy-ish, so they were in jeans, but since it was in our office, we wore business casual. At meetings in their office, we wear jeans. If we go to a jobsite, it’s jeans. If it’s an executive meeting, it’s suits or jackets.

    All I’m saying is I think in manufacturing, there could be enough variation in what attire is appropriate, depending on the situation, that I would be inclined to remind everyone what to wear for specific meetings.

    1. Judy*

      I’ve certainly been party to those conversations. Overseas travel, what do they wear in the Italian office? Do I need to take jeans and safety boots for the trip to Mexico or are we only staying in the office?

      In the first year of our marriage, my husband was going to Germany, and found out the client office wore tie & shirtsleeves every day, while locally he pretty much wore either polos or button downs with no tie. He found out the night before the flight, and had to work late preparing for the meetings. I ended up going out and buying 5 shirts and ties for him that evening.

  9. Seal*

    Whenever I do presentations or attend important meetings, I always make a point of dressing up. If I have to take staff members with me, I always advise them to do the same. I don’t make a huge deal about; generally along the lines of “don’t wear jeans”. I’ve also told people who are interviewing for positions both internal and external to make sure to wear a suit. While I generally trust my staff’s judgement when it comes to attire, I’ve found that they don’t always realize the importance of particular events and want to make sure they don’t find themselves in an situation where they are uncomfortable because they didn’t dress for the occasion. Plus I’ve seen too many badly or inappropriately dressed people at events to not feel compelled to speak up in advance.

  10. Zillah*

    I don’t there’s anything wrong with asking if he thinks that there’s a problem with your general attire, but can you elaborate on what other issues you’ve had with him? That might change my take on this.

  11. Ann O'Nemity*

    Although I’ve heard male bosses remind female employees to dress nicely for certain work events, I can’t remember a single time that I’ve heard a boss (of either gender) call out a male employee and ask him to dress nicely.

    1. Yet Another Allison*

      It might depend on the context, but it’s pretty common in my world. If fact it is so common that men will ask “Is this a tie thing?” when there is a work event coming up. My point is that context matters a lot, so I wouldn’t go straight to the gender bias conclusion.

      1. Sascha*

        I agree with this. At my current workplace – which is very, very t-shirt and jeans casual – I often hear the men get reminded to wear something nicer than t-shirts and jeans to things, whereas most of the women dress a little nicer than that anyways.

        1. sunny-dee*

          Yeah, same in mine. I’ve only had one event where a manager sent out a general dress-code warning, and it was directed at the guys, not me and the other woman on the team.

        2. Jen RO*

          Same at my workplace. We are very casual, but sometimes the office manager sends the odd “clients will be on-site, please no shorts and flip flops!”. (Actual email, and I am 90% sure it was aimed at the guy sitting next to him, who always looked like he just got back from a vacation at the beach.)

      2. Adam*

        Happened to me for sure. Our office has a range of dressy to casual business attire, depending on the department you’re in for the most part. I probably dress more casual than I should, but I’ve kind of stopped caring and my job requires a fair bit of moving around and lifting that no one else does so I feel justified it not dressing very professionally. But when bigger public facing things come around that I have to go to I’d always get a casual mention that my attire needs to spiffy up for that, so no big deal.

        It’s gotten to the point that whenever I do dress nicer for the hell of it people always ask if I’ve got an interview somewhere (0h how I wish…).

      3. Ann O'Nemity*

        I should clarify. I have seen mass emails or heard announcements about the dress code at upcoming events. Such as, “The dress code for the holiday party is black tie.” Also, I’ve heard of cases where a man received feedback on attire after he had violated the dress code or norms.

        But I’ve never heard a boss call out a man specifically to tell him to dress nicely for some upcoming meeting or event. I’ve heard a lot of comments like, “Betty, remember to dress nicely on Friday because we’re meeting with the VIP clients!” I haven’t heard the same kind of comments directed at men.

        1. Yet Another Allison*

          No, I understood. And that is exactly what I have heard. Common conversation:

          “Remember guys, this is the sponsor so it’s a suit *and* tie meeting.”
          “I have to wear a tie?”
          “Yep, sorry.”
          “How about a tuxedo T-shirt?” (seriously this joke is so old)

          Like I said, in some environments it is totally common.

        2. LucyVP*

          I have definitely reminded my male employees about dressing up for a meeting or event.

          And just last week I had to say something to my male assistant about his button down shirt that he wore for a board presentation (it wasn’t quite ironed).

          But – like others have said we are a very casual office normally, so days when donors or board members are around the difference is dramatic rather than slight changes.

        3. Ludo*

          I have. Many times. And I have told men to dress up for events. Heck, just today I just told a male direct report to do so for our meeting with the CEO Friday.

      4. Bwmn*

        At the last nonprofit I worked at that had an aggressive casual/informal dress code – it was my job to give staff dress reminders if they were meeting donors with me. My boss would have me just give reminders to female staff, and then for male staff it was usually a more drawn out process of “DO wear this and DON’T wear that”.

        So while I think it’s industry specific whether or not that happens, it definitely could also be the gender element that meant that for my male colleagues being told how to dress was such an anomaly in their general lives that it required more emphasis.

      5. Jamie*

        Absolutely. In manufacturing and we’re definitely on the casual side of business casual so it wouldn’t bother me in the slightest. I know what events call for grown up shoes and when I can be myself – but it’s asked and answered here all the time.

        It’s also possible as he sees the OP so seldom that the people with whom he works are super casual so he’s just covering the bases. And it’s also entirely possible that he doesn’t think the OP was formal enough in previous presentations and is trying to hammer it home without being more direct, which sucks, but isn’t uncommon.

        Because I have worked with people for whom dressing up means wearing their good jeans with a polo instead of a t-shirt – so if I were the OP I’d make sure they were on the same page with what is expected.

        1. Marisol*

          Standard operating procedure at my work – an email that says “vip client will be here on Friday morning so men will need to wear a jacket and tie, and women the business formal equivalent.”

          Some events require a jacket, but no tie, and this is specifically spelled out as well. Clothing gets policed around here but the women invariably have more latitude.

          The men usually have a spare tie in their desk drawer and every so often someone will call me and ask if the boss was wearing a tie when he went into that meeting, so they can get on the same page.

          I think for men, it’s like putting on the uniform: “coach told me to put my uniform on!” and not inherently disrespectful, but since women use their clothing more for personal expression, they are more likely to take offense.

          1. Marisol*

            The only time I have ever heard someone taken to task for their clothing was at my current job, between two men. A vp came in on Friday with light blue, chambray-ish chino pants, and the boss questioned him about wearing jeans. A light-hearted, yet serious debate ensured between the two men, in which all the vp’s coworkers offered their opinion, on what made something “jeans” or not. It wasn’t exactly handled with sensitivity, but it was understood that it was the boss’s call to make and the vp didn’t seem to be hurt or offended.

    2. long time reader first time poster*

      Of course not. And that’s why I’m bristling a bit at the suggestions to just let it go. It’s BS.

      The ‘confrontational’ bit probably is, too, to be honest. In my 20+ years as a worker and manager, I’ve never seen a man being told he needs to be ‘nicer’ in his interpersonal communications, even if he is brusque. A woman with the exact same conversational style? Many times. It’s gender bias — women are expected to be softer, kinder, more touchy-feely.

      Anyway, as to the OP, I would certainly question the manager as to what his concerns were. If I could, I’d try to do so with a bit of humor, if I didn’t think that would backfire.

      1. Ask a Manager* Post author

        I’ve told a man that. I think I’ve told more men that than women, actually. I absolutely agree that women hear it more, and in cases where men wouldn’t, but I do want to register for the record that some men have been told it, because I’ve told them :)

    3. Fucshia*

      That happens all the time at my office. Our normal attire is business casual — no ties or suits most of the time and jeans on Friday. But, if someone is presenting, their attire is expected to be more formal and men are reminded to dress up and wear a tie.

    4. some1*

      Once. When I was an admin in a law office, one of the male student attorneys was told by the (male) attorney supervising him that he should wear an undershirt.

    5. MaryMary*

      I have heard bosses talk to male employees about the dress code. At OldJob, another manager at my level had to talk with one of her male direct reports because he was wearing shredded jeans and you could see his boxers through one of the rips (we had a casual dress code but holey jeans were not permitted, and of course visible underwear at work is never good). I know another manager who sent a man home to change because he wore a football jersey to the office, and we weren’t allowed to wear athletic attire (this wasn’t a one-time offense and he had been warned). As a manager, I’ve set dress code expectations with my reports for client meetings. “You should wear a dress shirt but you don’t need to wear a tie” type conversations. I’m not saying there isn’t a double standard in some situations, but dress code conversations do happen for both genders.

      1. Jamie*

        I have absolutely heard more men being talked to about the dress code than women by far. And I’ve even had male managers admit they won’t discuss it with women unless it’s clearly inappropriate as there is too much variety in women’s clothing so they don’t always know what is and isn’t over the line.

        Absolutely men get called on this way more than women in my world.

        1. MaryMary*

          When I get a new manager, I’ve gotten in the habit of asking if they have any pet peeves so I know what not to do. A couple years ago, I asked that of one manager and she said that needing to have dress code conversations really set her off. I was a little surprised, because she was pretty senior and all of her direct reports were managers themselves. She said that when she was a young manager, she was the only female manager in the entire division. Every time someone needed to have a dress code conversation with a female direct report (which happened pretty frequently, it was a lot of people’s first job out of college), they pulled her into it or dumped it on her altogether. She said she had dealt with enough dress code issues to last a lifetime, and never wanted to have another for the rest of her career.

        2. Mister Pickle*

          Heh. I have been the target of more “dress code discussions” than I can count. I was not really a good fit for the Federal Systems Division. Then I transferred to Austin, where no-one cared.

          Oddly, in almost 30 years, no-one has ever “counseled” me on my hair. Which I know for a fact made some of the folks back in Federal extremely unhappy. But for whatever reason, no-one ever took me to task on it.

    6. My two cents...*

      oh, they do it all of the time at our office of only 15 folks. one guy seems to live in the most literal definition of ‘business casual’ possible. for example: he wears a button-down shirt every day. but that shirt is stuffed into the waistband of his 10+ yr old faded/light levi’s, without the aid of a belt. the office sends out ‘office wide reminders’ when customers visit, but we all know it’s really just for sticky steve who has perpetual jam hands like a 5 yr old.

      with guys’ clothes, it’s pretty black and white (standardized?) as far as ‘tiers’ of formal wear go. jeans vs khakis vs dress slacks vs suit, or short vs long sleeves. business formal means suits, whereas business casual means at LEAST khakis. with women, every different article of clothing (suits excluded) can vary between extremely casual and business. you can have casual khakis and dress khakis…or khaki-colored dress slacks…or a casual dress with a cardigan and boots, but then the dress can be formal when paired with closed-toe heels and opaque nylons.

      there’s always some bit in women’s magazines about ‘taking a look from day to night, from the office to happy hour’ which really shows the subtle variances for women’s clothing. don’t see stuff like that for dudes.

      1. Elizabeth West*

        the office sends out ‘office wide reminders’ when customers visit, but we all know it’s really just for sticky steve who has perpetual jam hands like a 5 yr old.

        This made me giggle.

    7. Hillary*

      My boss wore a pair of khakis held together with a safety pin for a couple months. They didn’t disappear until I had a humorous opportunity to ask him to not wear that pair during a VP-level business review with a strategic partner.

  12. Katie the Fed*

    3 comments over the course of a career probably isn’t something I’d mention. It’s annoying, but the benefit gained by saying something is almost non-existent, especially compared to the risk of coming across confrontational or argumentative. I’d just ignore it.

  13. BetsyTacy*

    Genuine question- can you get a friend whose professional and fashion advice you trust and ask them to look at what you’re going to wear?

    I ask this with love because I have known/worked with/had as my mother a number of people who thought they were dressed perfectly professionally when in fact, they were not. It may be an issue of styles changing or norms- a blazer plus slacks may be totally okay with one boss whereas another may see a formal suit as the only option.

    If this is my mother writing in, I know that you’re a hippie but you can’t always wear long skirts and drapey sweaters with clogs in every situation.

    1. OP*

      I am not your mother, but I have been doing as you suggested — asking a co-worker for advice. It has been working well.

        1. OP*

          Her opinion is that there is no problem with what I have been wearing to the meetings. What I am wearing fits in well with what others are wearing. However, I like the idea (that is somewhere else in this long thread) of asking my boss if his idea of “nice” and my idea of “nice” are two different things. Perhaps he expects me to dress up more than the people I am meeting with — I have been been meeting them where they are.

    2. OhNo*

      It wasn’t my mother, but I definitely have known a few people who follow the “hippie dress code” for every occasion. One of my professors in college, for example, was well-known for wearing flow-y, tie-dyed skirts under the graduation gowns every year.

      More to the point, however, I second the motion. Before you say a word to your boss, just ask someone to double-check your wardrobe choices. It’s possible they’ll see something you don’t that might be throwing up red flags for your boss. It seems unlikely, given that your boss sounds a wee bit sexist, but it never hurts to be sure.

  14. Maggie*

    Comments like that can be annoying because they are quite patronising. If we are professional something like dressing smartly is second nature if we work in a more formal environment. I’ve learnt to try and brush off annoying comments with a light-hearted comment of my own, e.g. “OK, I’ll leave my jeans at home then”.

    Old-fashioned male bosses can be a bit funny about clothes though. They are used to men wearing suits and ties but aren’t quite sure how women fit into this. This may sound a bit daft, but do you talk to your boss through Skype or videolink? If not, maybe he doesn’t even realise how smart you normally are.

      1. Formerly Bee*

        (Changing my name so that I can find conversations by Ctrl+F more easily. Bee -> Formerly Bee.)

        He probably has no idea how you usually dress, and he could be simply trying to make sure everyone’s dressing appropriately. Or I might be too optimistic about this.

    1. OP*

      I think, perhaps, if he had said “Please remember to dress professionally for this meeting.” I might have not had as adverse a reaction as “Remember to dress nice.” Then again, it is possible that I would’ve been just as annoyed by it. It’s hard to know.

  15. AB*

    Having worked in a diplomatic office has kind of skewed my viewpoint on this. There were tons of events every month in various stripes of formality. It was absolutely normal to send out invitations and then get 50 phone calls or emails asking what people should wear. I mean, I would get people asking “is this a tie/ no tie suit event” or “Is this pantyhose and heels business or loafers business” “Is this black tie tux formal or black tie suit formal”. These questions came from other diplomatic offices, mayors, governors, you name it. When I got an invite for my boss, one of the first things I would do is find out what the acceptable level of dress was.

    When I moved to corporate, I just kept it up, and my boss really appreciated it. I never thought of it as inappropriate to put a note on my boss’ calendar that a meeting was suite and tie or khakis, and if his reports were going to a meeting where there was a certain expectation for the level of dress, I would send out a reminder email.

    1. aeldest*

      But I think there’s a difference between clarifying the formality level of an event and simply saying “make sure you dress nice!”–one is helpful information, and the other is what you tell your 10 year old on picture day.

  16. LawBee*

    I’d let it go, or circumvent it with a “and I’ll be wearing a suit for the presentation” comment. but one comment once a year isn’t worth it.

    1. The IT Manager*

      By this point, I’d probably respond to the “dress up” comment with a “I was planning on it” which could be a bit snarky or not depending on tone, but still feels less confrontational that the direct question suggested by the LW and Alison.

      1. Ask a Manager* Post author

        I didn’t intend mine to be confrontational! (Although I suppose it could, depending on the tone.) I meant it to be delivered in a tone of genuine, polite curiosity.

        1. The IT Manager*

          Tone can make a big difference, but perhaps “direct” is the best term. I am wimp about having difficult or uncomfortable conversations which I know is a problem, but I am also not sure I could pull of the the genuinely curious tone.

    2. jag*

      If this is something he says only rarely, and only for things that are very important for him, you should let it go and perhaps say something like what LawBee said. Yes, it’s condescending. But he’s also probably nervous about the meeting and wants stuff to be perfect so he’s saying stuff that probably isn’t necessary.

      If he was frequently saying this to you, it would be a bigger deal. For every three months or so? Let it go or better yet, confirm to him that you do that with something like what LawBee said.

  17. OP*

    Thank you, everyone, for your perspectives. A few things:

    1) He has only been my boss for the last few years, so we don’t have a relationship going back years.
    2) I agree with whoever suggested (or it just might be in my mind) that he sees me as a reflection of him when I am presenting and therefore wouldn’t want anything I do (or wear) to reflect poorly on him. This makes a lot of sense because he it very focused on appearances. I can handle the comments if they are coming from this place.
    3) I do plan to ask him sometime, just casually, if he has heard concerns about my general appearance. I am a casual dresser, but so are most of my colleagues at this location (picture jeans and a nice top on a regular basis). His location tends to dress up more (khakis and dress shirts for men), so that may be part of where the friction is coming from.
    4) I am also, in general, amping up my personal wardrobe because I have noticed that those who are higher up in the organization tend to dress up a little more than the rest of us, so I figure that if I do it, too, it might make it easier for people to see me in that role.
    and 5) As for his gender bias, I have been addressing it with him through HR. It is more covert than overt, so there are few things I can point to and say, “See, sexism!”, but HR has taken his comments and overall attitude toward me seriously.

    Thanks, again.

    1. some1*

      I think this is probably all about #3. He probably doesn’t have an issue with the casual dress most of the time, but just wants to reiterate that you dress up more for the presentations. And that’s probably a little mico-managery of him but probably not worth pushing.

      1. OhNo*

        I think it definitely has something to do with #3. Especially if he is aware of the difference in dress between the two offices, and an appearance-aware sort of person, it seems like he just wants to make sure that you know what his expectations are for you in this circumstance.

        Not that it makes the comments themselves any less annoying, but at least it doesn’t sound like they are deeply rooted in sexism or anything like that – just unfortunate phrasing surrounding a legitimate expectation.

        1. jag*

          Yes, reading this, I’d assume he wants you to be at the top of your game, as in 3 and 4. He’s trying to be certain.

          He might be a male chauvinist, he might be obnoxious, but if you’re routinely in a more casual office and your clothes are not (yet) at the top of what is appropriate in the company’s most formal situations, him saying that to you before a key meeting is reasonable, even if it’s probably not necessary.

    2. Not So NewReader*

      I grew up around family members that were all about appearances. Reality was irrelevant- and appearances were where it was at. It can be difficult to respect someone who seems so concerned about superficial things.

      I would let him have that- you can use it to beef up your game. (Everyone can beef up their game- goodness knows I could!) It’s only a feather in your cap, when you can turn to HR and say “Look, he told me to do X and I did; he told me to do Y and I did; etc”.

      I get that this is a very annoying person, I can see that. However, pick your battles. Make sure that the battles you pick you will win. As others have pointed out, this particular battle does not look like it will be a strong course to pursue, for various reasons.

      I am kind of avoiding the issue about his concern about how things appear because that works into an endless discussion. And the bottom line is that sometimes annoying people say things and mean it to the extent that it is said- they do not have an underlying negative nagging message, even though it sounds like they do. Follow up where you have substantial basis and let the rest of the stuff go.

      1. OP*

        (snip) I am kind of avoiding the issue about his concern about how things appear because that works into an endless discussion. (end snip)

        This would open up a huge can of worms with this guy, but thanks for letting me see his comments as part of a larger pattern.

  18. MaryMary*

    I agree with Alison that you should follow up the next time he says something. Like a couple other posters have mentioned, maybe you are a touch too casual, or he has an elevated sense of how formally you should dress. I work in a traditional office, our dress code is very conservative. Nearly all of the men wear suits, and the ones who don’t wear dress shirts and ties. I’m more comfortable in a dress than a suit, so I usually wear a professional dress and add a blazer if an event is especially formal. No one has told me I should wear a suit (most of the other women in the office don’t, and the ones who do don’t wear one every day), but it wouldn’t be out of line if someone told me that I needed to wear a suit to a a certain meeting. However, if they told me to dress up or make sure I dressed nicely, I’d be sure I wore heels and my good jewelry, not necessarily a suit or “interview attire.” Maybe you do have a disconnect.

  19. MK*

    OP, is it possible that your boss says “dress nicely” when he means “dress formally”? Could you be going for bussiness casual, when (in his opinion at least) the presentation requires a suit?

    Also, while gender bias in how men and women dress in the workplace is a reality, it’s also true that it’s easier for men to avoid a faux pas in that area. I would assume that your male colleagues would take it for granted that a presentation to the senior vice-president and his team means they have to wear a suit and tie, preferably in conservative colors and patterns. A woman might think that a long-sleeved business dress without a jacket is formal enough and be wrong-footed when everyone else present wears suits. (And don’t get me started on the fact that a man can get away with wearing the same three suits, while a woman is judged if she repeats an outfit twice in ten days ).

    On the other hand, if these were clients instead of higher-ups in your own company, I would consider the possibility that you boss might expect you to dress more expensively in order to impress them, some workplaces have that attitude.

    In any case, I don’t think there is any harm in responding to his reminder with a question about whether he has specific concerns about your attire or if it’s just an automatic reminder. Just don’t do it in a confrontational tone; make it a genuine question.

  20. Lisa*

    Reminds me of ‘smile’ – hate those people.

    I had my boss tell me I looked nice 6x one day. We had a client meeting that day, I wore a skirt. I didn’t have issues with telling my boss how I felt back then, but did as time went on and it was clear that he was a condescending jerk to all women and wore me down with his gender-biased comments. Anyway, at the 6x time of ‘you look nice’ in one day – I said – ‘how often do you tell Luke, he looks nice? how often do you throw a pen at him in a meeting? when is the last time, you jostled his chair as you went by his desk? stop doing it to me, its annoying’.

    I wish I kept that fearlessness, but he wore me down after 6 years.

    1. Not So NewReader*

      I have always wondered if the “smile people” realize how silly they look when they say “smile!”. They look like they can’t think of anything else to say.

  21. Annika Potato*

    Hmmm… I think it is possible that the relationship has deteriorated so much that fairly benign things are beginning to irritate the OP. Honestly, in her follow-up, the OP mentions that she is adjusting her dressing to be more formal, and that her manager’s office is more formal than hers.

    And the truth is that women’s clothes are more varied than men’s are and thus more easy to screw up. Most men think formal = suit. Suits are long sleeved jackets and full length pants in sober colors with a shirt and a tie and similarly colored closed toed shoes. Business casual basically means take off the tie and jacket.

    For women, formal is a suit, fine. But what a mismatched suit? Does it need a classic shirt? What about a shell? Or casual top? What about statement jewelry? Short sleeved jackets? No jacket? What about a shift dress in heavy suit material? Or a plain black dress? Above the knee is fine? Bright colors? Open toed shoes? Also make-up – is e.g. bright red lipstick conservative enough to be in business formal? And business casual is a minefield!

    1. Jamie*

      This is such a great point – and it is complicated. The men in my family (and most men I know) have 4 categories of dress:

      1. Casual (whatever they feel like)
      2. Semi-casual (chinos and sweater/pullover)
      3. shirt and tie
      4. Suit

      That’s it. We, on the other hand, have to evaluate each outfit and determine if it’s the right level of formality. Slacks? Maybe, depends what kind – could be too casual or too dressy. Blouse? Maybe – as long as it’s not too cocktail party-ish, or too running errands-ish.

      Like being freaking goldilocks – trying to find something that’s not too much one way or the other and hitting juuuuust right is tricky sometimes.

      1. sunny-dee*

        Also, what seems very acceptable to me — like, a Banan Republic wool sheath dress with pumps — doesn’t seem like a suit to my dad because it’s not a traditional skirt-blazer suit. Also, only stockings seem formal, if I wear black tights (winter) or go without stockings (summer), it doesn’t seem like business formal to my dad, just church dress. He’s pretty old school.

      2. cuppa*

        Yes! I think back on one of the first office jobs I had — the dress code was formal — shirt and tie for men (easy!). But there wasn’t a whole lot of clarity on the women’s side, and although I was never talked to about it, I think back and cringe on some of the things I wore. They really probably weren’t formal enough.

  22. De(s)sert Duchess*

    A year ago, the good people at ExJob organized a lovely Christmas dinner. But unfortunately it was only lovely up to a certain point – that point being when a group of 5 people from my department announced they had a “surprise treat” for everyone.

    This turned out to be the five of them donning Santa hats and soulfully serenading our boss with what can only be described as a very … interestingly pitched … a capella rendition of “What A Wonderful World”.

    I had no part in it, had no idea they were organizing it, but as soon as it started my cheeks flamed and I cringed so hard in embarrassment that I basically folded in on myself.

    There was a long, long silence after they finished, and then my boss remembered to fix his smile back on his face and mumble something nice.

    1. Jamie*

      You win. I can’t even watch people sing badly on TV I cringe so hard in embarrassment for them – I cannot even imagine.

      If this is what they came up with I shudder to think at what ideas were rejected.

      1. De(s)sert Duchess*

        Afterwards – once I was able to look any of them in the eye again – I was told they’d considered a dance routine to go along with it, but there “hadn’t been enough time” to organize it.

        I’m pretty sure I managed not to say “oh thank f*ck” out loud, but it was a close shave.

    2. Judy*

      I did work at a place that had caroling on the last Friday afternoon before Xmas. They would walk through the building and stop in the rooms and sing a song or two.

  23. D*

    I do think the OP’s friction with her boss might be coloring the interaction, but I respectfully disagree with a lot of the comments that this is not an issue. OP stated that the boss doesn’t tell men the same advice and that there are other signs of sexism with this boss. If both of those things are true, this could be viewed as questioning her judgment and as subtle sexism. It’s similar to men telling women to smile. Although this particular behavior by itself could be benign, lots and lots of little behaviors like this can add to up a big deal if the boss views her as having bad judgment because she is a woman.

    I don’t think that the OP should say to him or HR, “You’re being a sexist pig by telling me how to dress!!!!!!!!!!!!!!!!!!!!!!!!!!!!” But asking whether there’s been concern about her dress is a good middle ground, in my opinion. She might learn something useful if she has been dressing inappropriately, or the boss might realize he has been a little patronizing if there aren’t any concerns.

    1. sunny-dee*

      I recently had a coworker quit, and one of her complaints was that our manager was sexist. They definitely had personality conflicts, he did single her out for certain kinds of criticism — but he did that to everyone. She just didn’t see it. (I heard him make some snarky comments about two other coworkers, both male, right along the lines of the comments that my coworker complained about.)

      Really, my manager just has a prickly personality and a tendency to push at people. But to ExCoworker, his prickliness and tendency to push were a sign of sexism, and it really wasn’t. It was just a sign they didn’t get along that well.

      1. D*

        That totally happens.

        My point (which I did not articulate very well) is that sometimes these little things are only directed at women and some bosses are jerks with gender biases. Certainly there are plenty of situations where there’s a misunderstanding or the person who feels aggrieved doesn’t have all the information. But if we give the OP the benefit of the doubt and believe that this is one thing in a pattern of behavior (that apparently HR has also taken seriously), then it’s not necessarily NBD.

        Most of the commentors seem to be saying that there are situations where this might not be gender bias. I just wanted to throw in a little support for the OP and agree with her that sometimes it can be gender bias, and she’s not necessarily reading too much into the comments, given that there are apparently some other circumstances that we don’t know.

        1. OP*


          He does only direct this to the women in the group, mainly me because I am the only non-administrative assistant at the corporate headquarters. I do plan to pay more attention to his patterns of behavior and our interactions.

          I am trying to improve my relationship with him and this was one of the upcoming things I was dreading either (1) not responding again, or (2) responding poorly. That is why I am asking for advice.

  24. HR Manager Here*

    You never know, he could be getting feedback about your attire, and other things, from your coworkers. That may not be a far-fetched notion considering he doesn’t see you very often.

  25. Vin packer*

    Suggestion: I would love to see a column about microaggressions in the workplace. (For those not familiar: They’re “micro,” but their demoralizing effects build up over time, and the perpetrators might not even realize they’re doing it. How do you effectively choose battles with a serial microaggressor, especially when each one is separately not big enough to fight? Sounds like that might be part of what this poster is dealing with.

    1. D*

      Yes! This is what I was talking about above; I just didn’t realize there was a word for it. Thank you for the link.

      I agree this would be a great topic.

      1. Vin packer*

        Its a great word. Just having a label for it in your own mind can be steadying, even if you ultimately don’t push back.

    2. OP*

      Thank you! I think that this is what I was trying to get at with the “his sexism is not overt, but more covert” comment above. I am going to read more about this. Thank you!

    3. OP*

      I thank you, again, for this post. This week, I started listening for these microaggressions and my boss did not disappoint: “Please write this email (blah blah blah); I am sure you will be able to be direct, but with no venom…”

      I was so surprised, I wrote it in my notes of the conversation.

  26. Purr purr purr*

    I don’t think it’s that big a deal. I doubt it’s even that he feels the need to tell you; I suspect he used to work with someone who didn’t take it seriously and he’s just making sure that you and him are on the same page. I can see how it would be annoying though. My own cousin sent me a text telling me to wear something smart and black to my grandfather’s funeral. I think some people just don’t understand that the rest of us do actually have some common sense and can manage without them reminding us!

  27. Mister Pickle*

    This is just my naive opinion, but I think that when people say stupid stuff like “dress nice”, it comes from – laugh if you want – the person wanting to be helpful. It may not be appropriate, it’s almost certainly not appreciated, it may be sexist, it may be a form of micromanagement – but at the root of it all the guy is standing there, he wants you to do a good job, but practically speaking there’s not really much he can do to help – except give you the benefit of his sage wisdom: “dress nice!” There’s every chance the guy feels really stupid right after he says it, too.

    I’m not privy to the details of the relationship, but I wonder: if the boss says “dress nice!” again, OP should tell him “the tradition in theatre is to say ‘break a leg’ when you want someone to do well”. And maybe he’ll cut it out with the “dress nice” thing and say “break a leg!” instead.

    I could be wrong. But there’s something about this that seems less like the guy is consciously trying to be insulting, and more like he simply feels the requirement to say something – and he’s fallen into this habit of saying something annoying.

    (I prefer to think of this as coming from the realm of cognitive psychology – although if it sounds more like NLP, well … you’re not wrong)

  28. Office Worker*

    My boss does the same thing. I’ve worked with her for three years and she’ll still tell me when bigwigs are expected “Be sure you look really nice. You know, makeup and everything.” I look nice every day but wear minimal makeup as it’s not my thing (generally just foundation and powder, lipstick and mascara). I always just smile and say “Don’t worry. I was planning on looking EXTRA pretty.” And then I follow through–lipstick a little brighter than usual and wear eyeshadow instead of just mascara alone. It does get annoying sometimes but I just shrug it off and not make a big deal of it.

    1. long time reader first time poster*

      OMG I would flip if somebody suggested I *had* to wear makeup for anything. Flip.

      It is so none of anybody else’s business.

    2. OP*

      That is something I didn’t think of — I don’t wear makeup. It’s a personal decision I made years ago.

  29. Mallorie, the recruiter*

    We have a jeans office, so I do tell people to “dress professionally” when certain bosses are coming in. I also recently DIDN’T talk to an employee about dressing for an interview, and really wish I would have! They were dressed to casually, and looking back, I wish so much I would have specifically reminded them to suit up! These are not teenagers, most people on my team have several years of office and professional experience. But in a casual environment, even professional people forget sometimes what’s normal and what’s not.

  30. Mindy*

    Deja Vu. In my first job I was told by my supervisor to be sure and “dress up and look nice” for a particular event the next day. I thought I did, several other employees even commented on how nice I looked. Several months later I was docked on my performance appraisal for purposely disregarding/ignoring direction from a superior. Apparently she felt lipstick (I didn’t own any) was an essential part of looking nice. This has been a long time ago, but I guess some things never change. I agree it might be a good idea to find out what your boss has in mind.

  31. EvilQueenRegina*

    I had a coworker once who was asked to minute some important meeting, but the guy chairing it was worried in case she wore something low cut, as she sometimes did, so he asked another manager to have a quiet word to her about dressing up beforehand. She made a few jokes about getting the boiler suit out, but went along with it and on the day she wore a white shirt with a jacket. Problem was, on the day it rained heavily and in the time it took to get from the car to the building where the meeting was…well, let’s just say she wasn’t revealing any less by wearing the higher necked shirt!

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