I was bcc’d on an email to my boss about his unprofessional outfits

A reader writes:

I work at a very small nonprofit with a very casual dress code (i.e. jeans and t-shirts are fine, although most of us dress business casual by choice) and am known around the workplace for having good taste in clothes and being well put-together. My boss, however, regularly wears performance fabric/bike gear to the office, as well as to meetings with possible grantors/investors. Our COO has been on a long crusade to get him to dress better as well, and my boss himself acknowledges that he’s “a bit of a slob.”

There have been a few times that I’ve gently reminded him about upcoming big meetings beforehand, with the aim of getting him to dress more professionally, mostly because I often am included in these meetings and don’t want to upstage him. He seems fine with me reminding him and does clean up a bit on these occasions, but sticks to very-casual-casualwear the rest of the time, despite the general opinion around the office that his style needs work.

We just launched a project that requires the boss to meet with important partners and high-net-worth individuals on a daily basis. Today, the COO bcc’d me on an email to our boss calling him out for his unprofessional wardrobe — in general, it was a long, bizarre, and frankly kind of rude email. I emailed her back to say “oops, I think you accidentally copied me,” but she confirmed that I was intentionally included because she trusts my style instincts and wanted to know if I had any thoughts.

While I do agree that improving his wardrobe will help him (and our organization) appear more professional and serious, I’m uncomfortable with the way she handled this issue and with the fact that she included me in the conversation without my boss’s knowledge. I’d be happy to advise my boss if he asked me himself, but I feel put off by this whole situation and don’t want to be in the middle of what I suspect will be an ongoing issue. My plan right now is to tell him that I was copied on the email, because I think he deserves to know that I was privy to what was essentially a dressing-down (pun intended) from the COO. Any thoughts on how I should proceed?

Yeah, the COO shouldn’t have bcc’d you.

In general, bcc’ing should be reserved for reasons that aren’t sneaky. Bcc’ing is useful if you want someone to be aware of something but they don’t need to get the resulting back and forth about it, or where someone just needs to know “this was sent to X,” or where you’re keeping your manager in the loop about where something stands (“I addressed this issue we talked about,” “I received a testy response from the client,” or whatever). A good litmus test is “if the person I’m sending this to found out about the bcc, would it be a big deal?”

But bcc’ing you on a rude-ish email to your boss isn’t really appropriate. It’s undermining your boss, and it creates kind of an us vs. him dynamic, which is never good.

That said, I wouldn’t tell your boss that you were bcc’d on the email. If the COO starts regularly bcc’ing you, then you should talk to her directly and ask her not to, explaining that it’s putting you in an uncomfortable position with your boss. But if it’s just a one-time thing (which so far it appears to be), I’d let it go. The COO made a questionable choice, yes, but she’s senior to both of you and you don’t really have standing to undo her choice without her okay.

As for the larger dress issue, I’d keep doing what you’re doing: reminding him about upcoming important meetings, but leaving the rest to him and management above him. (And since it seems like now important meetings are going to be happening daily, I’d assume that this will come to a head one way or another — but you should stay generally out of the fray.)

Updated to add: The letter-writer clarified in the comments section that his boss is the head of the organization, so the COO reports to him, rather than being senior to him. My advice is still the same, other than that it might make sense to more quickly say to the COO, “Hey, I don’t feel comfortable being pulled into this.”

{ 84 comments… read them below }

  1. ThursdaysGeek*

    This sounds like a case where the COO should talk to the boss and tell him he needs to change: do the management she’s responsible for. But instead, she’s trying to push that off on an underling, hoping that the person under the boss will do the management that she wants to avoid. Sorry OP!

  2. OP*

    Thanks so much for your answer! I probably should have been clearer about this in my original email, but by “my boss” I mean the executive director of the nonprofit — the COO and I are both junior to him. That’s one of the things that made this exchange so weird.

    1. Ask a Manager* Post author

      Oh! That’s an interesting twist. I don’t think it really changes my advice though, other than that you might more quickly say to the COO, “Hey, I don’t feel comfortable being pulled into this.”

      1. ThursdaysGeek*

        It does completely change my understanding of the issue, however. (I guess that’s why we pay you the big bucks. Or something like that.)

    2. fposte*

      This is kind of mindboggling to me. The COO wrote a wild critical letter to her own boss and bcc:ed you to make you part of her, um, initiative? That sounds like an attempt to create that favorite passive aggressive attack of “The whole group thinks you need to change,” with the extra frosting of it being used on the boss.

      If I were your boss, I’d have some words for the COO. And if I were you, I would basically ignore this going forth and not even bring it up to your boss.

      1. Ask a Manager* Post author

        See, I read it as small nonprofit where the COO and ED probably have a very close working relationship and the COO knows she can take him to task over this kind of thing. (I totally could have sent an email like that to my ED, although I wouldn’t have bcc’d anyone and I also wouldn’t have done it in email.) And she’s bcc’ing the OP to convey “look, I’m going to take this issue on and get it handled, and I know you approve.”

        It’s totally inappropriate, but I think that’s what’s happening.

    3. snuck*

      Ok… so is this one of those really small offices where normal professional boundaries get blurred? Because I can totally see this happening in one of those offices… I’d much rather not have an email chain about it, but if they want you to help wrangle the Dress Offender then come and talk to you and say “look you have a way with Mr Sweaty Yeti, can you please help us here?” rather than a BCC on an email which is shady and leaves a trail.

      I’m not sure what your role is… or the relationship you have with the CEO… so take that into account with this…

      Can you say to the CEO “Hey mate, can I help you with anything about these daily meetings? Not just the reports etc, but … would you like me to arrange a place to store a jacket or similar for when you have to meet someone a bit more senior?”

      And … maybe that’s the crux of it. He doesn’t care enough to have a change of clothes at the office? If you looked at his style is there a simple way you could bring it a few steps forward? A smart sports coat? A pair of chinos? A change of shoes? Is it possible he’s wearing these clothes because he exercises on the way to or from work and doesn’t have anywhere to put his work clothes (and doesn’t need to care because he’s the CEO) – can you make that easier?

      Also… I’d point out to the COO that the funding came in, and the organisation is getting more funding, with the current sartorial status … it’s not harming anyone yet, so long as you are meeting goals and getting funding then it might be ok? (Not knowing the norms for your specific industry)

  3. ChelseaNH*

    If you have the right kind of relationship, you could suggest that your boss keep a change or two of “meeting” clothes at the office for those times when he needs to look more presentable.

    1. OriginalEmma*

      That is exactly what I was thinking. If he’s coming into work in bike gear, likely he’s a bike commuter. OP can recommend keeping a few pieces of professional clothing that all work well together (compatible button-down shirts, ties, trousers, two pairs of dress shoes, etc.) in the office so that the ED doesn’t need to remember them. Hygiene supplies might be helpful there too…but as a bike commuter, he may very well be aware of all this (because it’s common advice on every “I want to bike to work but not be smelly” question on the internets).

      1. kkcf*

        This is what I do when I bike commute. It helps when you work in a bike friendly area (but considering OP works at a startup I’m pretty sure bicycles are not some foreign object in their area). This is the second time reddit has been suggested as a resource in as many days but I really like /r/bikecommuting as a resource get new commuters into it and provide advice.

      2. Koko*

        “If he’s coming into work in bike gear, likely he’s a bike commuter.”

        Now I’m imagining some coworker who drives in but just enjoys wearing fluorescent Lycra capris and jerseys.

        1. Dr. Johnny Fever*

          Never considered that. My job is too long to bike commute, but there is nothing more comfy than a good jersey and a pair of compassion bike pants.

          Well, at least comfy everywhere except the crotch when not on a bike.

    2. Ihmmy*

      Precisely this. Since the OP already reminds sometimes about dressing up for meeting, it’s pretty easy to say something like “hey I know I sometimes remind you of upcoming meetings where fancier dress is recommended, do you think it might be easier for you if you kept a suit / slacks and a top here just in case something comes up?”

      My last CEO always kept a couple spare blazers in her office just in case she needed to extra fancy up, and she usually dressed very nicely

    3. BananaPants*

      Pretty much all of the managers and executives in my office keep a sport coat or suit jacket in their office – they’ll typically wear dress slacks and a button-down Oxford to work, so if they throw on the suit jacket it dresses up a business casual outfit immediately.

      Our 2 or 3 female managers/executives all do something similar with a blazer, but coordinating colors can be more difficult – a black blazer may not look so hot with navy slacks, you know? They seem to dress up specifically for events when they need to do so rather than winging it.

      1. PurpleMonkeyDishwasher*

        This is why my office blazer is charcoal gray instead of black – dark enough to be appropriately “business” in even formal circumstances, but it’ll still match navy. (Also, this is why I stopped wearing brown, because my matching abilities do not extend to appropriately pairing brown with gray, although the fashion internet assures me it’s possible.)

    4. Europa*

      My boss used to do this. He’d arrive in his bike clothes and if he didn’t have anything big going, he’d pad around in his socks and spandex all day. He did, however, keep a whole rack of dry cleaning nearby so he could change when needed. He had an office, but he didn’t like to use it, so it was basically used for meetings and to hold his dry cleaning.

    5. KR*

      This! We are business casual to casual here at my work (a town office building). My supervisor does not like dressing up so he keeps a coat/blazer thing hung up in the office for when he needs to look more dressed up.
      In this letter, it seems like the boss knows that his style needs some work. I’m wondering if, instead of challenging him, a more helpful approach would be for someone to gently suggest some easy and basic business casual wardrobe staples for him. He may simply not care enough to go shopping for clothes or figure out a style for himself. Whoever does this could be someone whose opinion he trusts and who has a decent rapport with him, and it could be suggested with links so that he can simply order the clothes right then and there without having to actually go to the store and try it on and go through all that mumbo jumbo (can you tell I hate shopping most of the time).

    6. Spooky*

      That was what I came here to say as well. Seems like the easiest solution.

      On another note, is the atheleisure trend moving into the workplace? I recently had a senior colleague who exclusively wore atheleisure clothes to work, but we work in fashion PR (and it’s very in right now) so I had simply written it off as an industry thing (I know we tend to fall outside the norm for most general business practices). Have other people seen this trend in their offices?

      1. anonanonanon*

        I’ve also noticed this, but I work in publishing on the East Coast which, in my experience, sometimes falls outside the norm. We’re also a region very fond of the atheleisure trend, so I’m not really surprised to see it happening.

    7. MKT*

      I do the opposite of this!
      I work in an office(generally on the more casual but nice end of the clothing dress code) but as a project coordinator for a construction company, some days I go in the field and some days I don’t, most of the time I don’t know which way my day will go. As a woman, that means that I need to have jeans, sneakers and an extra shirt with me at all times, in case I’m wearing a dress or slacks and blouse. I also have started carrying an extra jacket in my car for these cooler fall days, since I generally wear jeans to work, but I definitely don’t wear a heavy enough sweater for the office to go out and walk on a job site in.
      The funniest part is my project manager hasn’t yet caught on that I bring clothes/shoes to work for job site visits, so if he comes to the office in the morning or afternoon, he’s like, were you wearing that color earlier?

    8. Lucky*

      And if the Big Boss is bad at shopping, send him to a personal shopper at Nordstrom or set him up with a subscription to Trunk Club. His appearance is important to the company and they may need to put some money behind it to get it up to snuff.

  4. The IT Manager*

    What a mess! It seems like it would be responsibility of a person’s boss to tell them to dress better. Sounds like the sloppy dresser is the big boss with no one to correct him. The Executive Director’s subordinates – both the COO and LW – agree he should dress better for the good of the organization but obvious they haven’t had any long term improvement. Uggg! I think you need to let it go now or make one last ditch effort to sit down and talk with Executive Director before you let it go. He completely acknowledges the problem and refuses to change. You can’t make your boss change.

    1. Allison*

      Yeah, I agree with this. You can’t really “manage up” when it comes to someone’s work wardrobe, so if OP’s boss doesn’t have anyone over him, there’s not really anything anyone can do here.

      1. Bostonian*

        Well, there’s a board of directors who might be able to talk to the boss, depending on the type of board, but there’s no appropriate way for the OP or the COO to loop them in. It’s something they’d have to notice on their own through their interactions with the boss and decide to make an issue of it.

        The people best positioned to keep gently managing up may be those with some kind of admin role. When I was an executive assistant for a nonprofit CEO who liked to dress casually it was actually part of my job to remind him when one of his meetings for the next day would be at one of the golf clubs in our area that didn’t allow jeans or that he was going to be on camera for something and should therefore avoid shirts with narrow stripes or small patterns. I could easily have offered to put reminders on his calendars the day before big meetings if it had seemed necessary. It would have been pushing the boundaries a little to mention dress code type stuff when handing him materials or going over the week’s schedule or suggesting that he leave a change of clothes at the office, but if I were in OP’s position I would have done it.

        But my old boss understood business norms and wanted to be appropriate, he just needed reminders. (He actually had a finely honed sense of appropriate and often his just-slightly-too-casual was a conscious choice stemming from his personality and the type of work we were doing.) If he hadn’t cared at all, I’m not sure there’s any amount of nudging that would have helped.

    2. The Artist Formally Known As UKAnon*

      This exactly. OP can offer to help if they think it will be well (or at least not badly) received, but that’s it.

    3. Clever Name*

      Yeah. I agree with this. I had an old boss who frankly was a bit of a doofus. He would wear baggy sweatshirts and baggy jeans with holes in them. He wore white sneakers on a daily basis. He made a really big deal when he got a new pair; as if new sneakers really upped his style quotient (they didn’t). He once wore a new henley-style shirt (rather than the ratty sweatshirts and tees he preferred) to work, and my coworkers and I fell all over ourselves complimenting his shirt. We never saw that shirt again. :/ Some people just refuse to dress for anything but comfort.

      1. L McD*

        Bright white sneakers might be the only kind of shoes that arguably look even WORSE when they’re brand new. LOL. I’m just picturing him parading around proudly in his tacky shoes and it’s really brightening my day.

  5. voyager1*

    Honestly is the person BCC’d the same gender. I would be pretty ticked if someone though I need a junior employee to be basically my Mom for clothing choice.

    That being said I think Bcc is terrible and have only used it once. I am not a fan of it, mostly because how it can be used. My current employer does not allow one to use Bcc, it can be fire’ble offense.

    As for wearing tech shorts and shirts, well that is a little casual, but it isn’t the place of a junior person to tell a manger.

      1. Devil's Avocado*

        I’m not the person who brought this up: gender shouldn’t matter here, but I could never picture a junior male employee being tasked (or taking on the task voluntarily) to remind their boss to dress nicer for meetings. I’d bet everything on the junior person being a woman here.

      2. OhNo*

        Well, there is a certain risk of playing into gendered stereotypes with this issue, by assuming that all women are good at clothes, the LW is a woman, therefore the LW must be good at clothes. And there’s definitely some weirdness in the assumption that a woman would therefore be willing to “mom” their boss into dressing well.

        In this specific case, though, it doesn’t sound like it’s a gendered assumption – the LW specifically mentions that they are seen as a well-dressed person in the office. But I could see how, in a different circumstance, that could be problematic.

      3. Ann O'Nemity*

        One of the male managers once asked me to talk with his female assistant about her revealing clothing because he wasn’t comfortable having that conversation. Maybe that’s the thinking?

    1. JessaB*

      I only use bcc when it’s a mailing list where the other parties might not or should not have each other’s email addresses – IE some kind of party invite to a group where the individual members are not so close friends that they’ve shared possible work emails, but are close enough to me for me to invite them all. I use it as more of an information security thing not to hide that I’m telling someone something snarky.

      For instance I have friends who do not have my husband’s work email (there is no need for them to have it,) but if we’re planning during work time, I’ll bcc him.)

    2. Amy Farrah Fowler*

      I use Bcc for certain purposes. For example, I do hiring for my company and my boss likes to be in the loop about who I’m interviewing, so when I schedule an interview, I bcc her when I finalize the date/time, so she knows my schedule and can let me know if there’s any questions she’d like me to ask the candidate. I do think Bcc can be used in highly suspect ways, but that doesn’t mean it’s terrible all of the time…

    3. Angela*

      BCC is great for company wide announcements where tons of people might reply all when really only one person needs the response. Think internal promotion announcements – BCC everyone but cc the one promoted and then all the “congrats” emails only go to the person that sent the email and the one actually promoted. Also, my company frequently sends out emails looking for volunteers for various community service projects. If you BCC everyone, then only the person who sent the email gets all the replies on whether or not someone is able to volunteer. So their are valid uses, but to just BCC someone to be sneaky is ethically questionable to me.

    4. Koko*

      I use BCC occasionally when I need to email a large group of people who have not given me permission to share their email address with the group. The recipient sees that I sent it To: myself and that they were BCC’d and they don’t see any other addresses.

      Conversely, in my previous role as a major gifts nonprofit fundraiser, I harvested more email addresses than you know from emails where the sender did not do this. You meet the CEO of one company, and he emails you along with 15 other industry CEO’s personal direct email addresses. I know other people will do it because I did it.

    5. Sarahnova*

      I kind of felt the same. There seems to be a slightly weird vibe in this to me of the COO wanting the OP to “mother” her boss.

      1. Sarahnova*

        Oh, the OP is male! Well, that admittedly surprises me, and does change the dynamics, interestingly enough.

        Honestly, I’d be prone to say that until the day my boss actually asks for my style advice, I am not saying word one about it. He knows he ‘should’ dress better, he clearly doesn’t care, he’s the boss and apparently his organisation is doing just fine.

  6. AnotherAlison*

    I’m usually on team “dress-appropriately for work”, but I guess I’m in a mood today. Maybe dressing in spandex is working for the ED and the subordinates need to let it go. It seems when it comes to dress, it’s easier to widely miss the mark than to be a little off. Wearing khakis when you should have been in a suit seems to be worse than looking like you were going to a totally different event. Both stick out, though, for sure.

    1. Mallory Janis Ian*

      Maybe dressing in spandex is working for the ED and the subordinates need to let it go.

      This is what I came here to say. Maybe what the ED is wearing isn’t hurting him as much as the subordinates think it will.

      My former boss always dresses in a black suit jacket, a black or white dress shirt, dark-rinse Levi’s, and expensive black leather Italian shoes. My coworkers used to get all over me to try to get me to “make him dress better” for certain events, such as the school’s honors banquet or the professional advisory board gathering. I always thought he was fine the way he was, so I never said anything. Plus, he has a very definite sense of style, being in a design profession, and the way he dresses is a deliberate choice to present himself in a certain way. He was inducted into the American Academy of Arts for his profession, and he dressed the same way when he went to that awards ceremony and all the commensurate banquets, etc. I think my coworkers were more off-base to try to dictate his dress than he was to dress that way.

      1. AvonLady Barksdale*

        That sounds like the ad sales higher-up uniform to me! I can’t imagine anyone objecting to that outfit, unless your former boss spends a lot of time in a courtroom in front of a conservative judge.

      2. Chinook*

        “My former boss always dresses in a black suit jacket, a black or white dress shirt, dark-rinse Levi’s, and expensive black leather Italian shoes. My coworkers used to get all over me to try to get me to “make him dress better” for certain events, such as the school’s honors banquet or the professional advisory board gathering.”

        This is an issue? Around here, it is called a “cowboy tuxedo” and is perfectly acceptable business wear in many head offices (in fact I think the president of my current employer, a major pipeline company, is wearing just that today but probably with a slightly cheaper version of the shoes).

    2. Devil's Avocado*

      I totally agree with you. If I was the head of an organization I’d be pissed if my subordinates were that focused on what I was wearing. This guy is making choices that work for him. He doesn’t report to either of the subordinates – he presumably reports to the board. If there is a real problem (ie: if his dress is affecting the success of the organization), it’s up to them to deal with it.

    3. Koko*

      In a former job we worked with a stakeholder who felt he did his best work late at night, so he didn’t wake up until noon each day. He also had a thing about airplanes and refused to travel. When we had stakeholder meetings every other person flew in, stayed in a hotel, and was in the conference room by 8:30 am each morning for a full day meeting. This guy would stay home and we’d set up a conference line for him, which he would dial into around 12:05 pm.

      As far as I could tell, nobody cared. His business was wildly successful and his opinion was one of the most respected among the group of his peers. The kind of guy that if he didn’t weigh in on something, someone in the room would say, “Let’s hear what Fergus thinks about this. Fergus?”

      Some fields just don’t care as much about traditional business formality. Start-up culture is one of those worlds. Maybe fluorescent Lycra is part of his Personal Brand(tm) that he uses to attract investors.

      1. snuck*

        Yeah. We don’t know the field here.

        Having spent a good few hours at Guide Dogs for the Blind the other week I was a bit… overwhelmed at the massive structures and business suited assistants everywhere full of corporate art. It certainly wasn’t being put on for the blind people! But to impress me?

        I was thrilled to discover the dog trainers and people involved in the front line Guide Dog work were in polos and jeans/chinos. That was much more… realistic and honest… and helped change my view of the organisation.

        Work clothes are particular to industry sometimes. And send powerful messages. And sometimes a big corporate huff and puff mightn’t be the best message to send?

  7. Merry and Bright*

    I agree that BCC shouldn’t normally be used but there are some occasions when it is useful. For example, at one old job we had customers who subscribed to a monthly newsletter by email, and we always used BCC to keep customers’ personal email details confidential. I help out with a couple of voluntary groups outside where we use BCC for pretty much the same reason. But I agree that for ordinary work emails it should be the ecxeption rather than the rule.

    1. Carrie in Scotland*

      I’ve used it with students’ personal emails (before they have uni ones) for the same reason.

      I recently used bcc in 2 emails so that the person who was asking me to do x,y,z knows I’ve done it (external to my work but we work with them so need to keep them onside).

    2. Chicken*

      Using BCC to email to a group, when it’s clear that everyone has been BCC’d is pretty much never an issue. In fact, I’d be pretty upset if I subscribed to a newsletter and then they *didn’t* BCC everyone.

      I most frequently use BCC to send emails to large groups of people when I want responses, but I don’t want anyone else to get them (for example, sending 15 people a “can you please send me your current address” type email).

      1. Ann O'Nemity*

        Completely agree. The only reasons I use BCC is when (a) I’m protecting people’s contact info on a huge list, and/or (b) I’m preventing unnecessary reply-all’s.

    3. Xanthippe Lannister Voorhees*

      I wish my old grad school listserv had used BCC for department wide emails to avoid the irrelevant “reply all” issue! It definitely has a time and a place.

  8. Cat*

    I am always a lot less concerned about someone being rude to their boss about something like this and the other way around. The COO is an adult and can take the risk that she’ll get penalized for (rudely) speaking truth to power. It may not be the best idea for her personally, but it’s not going to hurt the boss career-wise and the boss is perfectly capable of dealing with the situation however he feels is appropriate. It’s kind of obnoxious that she copied the LW, but it was a BCC – the boss doesn’t know about it and the LW is under zero obligation to weigh in.

    Also, nobody should be wearing spandex athletic gear at work. Why do people do this?

        1. Koko*

          Laziness and lack of interest in clothes.

          I would honestly wear the same leggings and t-shirt everywhere every day if I thought it would fly. Clothes (at least normal/work clothes) are so boring to me that I seriously feel fatigued and groan to myself a little every morning when I have to pick out yet another work outfit.

          When I leave my workout I partly don’t want to change back into the clothes I was wearing before because I’m still damp with sweat and I don’t want to get into a fitted top and jeans. Sometimes it’s also because I’m too hot from the workout to get back into long pants. So I just leave the gym in my gym clothes. If I need to stop at the grocery on the way home, I do. I couldn’t possibly care less what the people at the grocery store think of my clothes.

          So, I understand the impulse to just not change your clothes because you’re comfortable the way you are and you don’t care what others think.

  9. Stacy London*

    Too bad What Not to Wear isn’t on anymore — the COO could have staged and intervention/make-over. Ha.

        1. AnotherAlison*

          I always liked the results in theory, but I sure wouldn’t trade my casual Saturday hoodie and jeans for a layered blouse/blazer combo. So many layers! I don’t think Stacey’s Saturdays were the same as my Saturdays. Home Depot and Wal-Mart barely require changing out of pajamas.

      1. MissDisplaced*

        Even for the guy who built custom boats and yachts. He went from grubby slob to professional looking tradesman. I think I had tears!

    1. Blurgle*

      You see, I always saw that show as teaching people who dressed badly and cheaply how to dress badly while spending ginormous amounts of money. Like ten years of my clothing budget on one shopping trip.

      1. Mona Lisa*

        But one can still dress well and cheaply. The idea is about finding clothes that fit well, flatter the body, and are appropriate for the person’s daily life. I remember seeing episodes where they sent people to discount stores like TJ Maxx, Marshall’s, DSW, Nordstrom Rack, etc. in addition to big box stores and boutiques in order to give people who might not be able to afford more expensive stores a chance to shop and locate appropriate items in places that they would have back home. I distinctly remember an episode where there was a woman with huge sticker shock so she was sent exclusively to discount stores afterwards, and she ended up with the biggest wardrobe in the show’s history.

        Personally, when I started watching the show in high school, I applied the rules to my shopping trips to places like Kohl’s and H&M, and I still have some of those pieces 10-15 years later because I’ve taken care of them and they were good wardrobe building blocks that were able to stand the test of time.

  10. Lily in NYC*

    Whoa, this guy is the COO’s boss! Not cool. I think boss should wear whatever the hell he wants and tell COO to back off. Poor OP should just say “keep me out of this”. My office is pretty conservative and we often have super-rich hedge fund guys come in for meetings – they dress like crap, even when the mayor or some other high official is there, and no one even bats an eye. Hey, Steve Jobs was the boss and wore dad jeans and the same ugly turtleneck every single day – can you imagine his reaction if he got an email from someone lower level than him telling him to dress better?

    1. Techfool*

      Absolutely agree with Lily.
      Boris Johnson could do with a haircut. But it’s also nice to see some personality.

  11. Erin*

    To address the larger issue at hand: I’m getting the impression he’s open to change (ie he admits he’s a bit of a slob) – is it possible you and the COO have been too subtle with your hinting and could benefit from being more direct?

    Obviously her email to him was probably pretty direct, but since it was also borderline rude, maybe he’s just put off by the whole thing at this point.

    Now, I going to go rogue and suggest something different from what Alison did. If you have a good relationship with your boss (and it sounds like you do), you could tell him you saw the email and use that as a jumping off point to really hit home that his wardrobe needs to change. Maybe you can phrase it like she showed the email to you and not emphasize the BCCing.

    “Bob, I want you to know Cheryl shared that email with me about your wardrobe. While I don’t agree with how she handled it, I do have to say…” And then be as direct as you’re comfortable being.

    A final thought: Maybe you could find an article on the importance of professional dressware and share it with him if you think that would resonate. Some people might be put off by that, though, but it could work if say…you know he reads Forbes religiously and you’re able to find a piece through them, or something like that.

    I guess I just feel like since this has come up several times before and nothing’s changed you might get more solid results from being semi-brutally honest, but of course this depends on his personality and the dynamics of your working relationship.

    1. Rocky*

      +1, for the perhaps weird reason that, if Boss knows OP saw the email, but OP didn’t agree with the bcc-ing, Boss can vent a bit. Venting is helpful because it gets him over any defensiveness. That might bring him round to thinking about the impression his clothes are giving.

    2. Meg Murry*

      Yes, I’m with this one. 99% of the time I’m on team “leave it alone” but I wonder if this is a case where the boss would like it if his “people” would handle it and just tell him what to wear, or even just make the right clothes appear. For instance, I work at a very small non-profit org (less than 10 people). Most days, we can (and do) wear very casual clothes, because we can get dirty or ruin our clothes in our line of work. But on occasion we have people coming in that the boss wants us to dress up for – and what some people were wearing wasn’t really up to par, but they had been significantly underpaid for years and the new big boss felt bad criticizing them. So instead, he had us each order 3-5 shirts that had our logos embroidered on them (paid for by the company, and he approved the final choices) plus a couple pairs of khaki or dress pants for people that wanted them. Then he could just say “so-and-so is coming tomorrow, it would be a good day to wear your logo shirts”.

      If (big IF) OP and COO wanted to tackle this, what if they just asked the ED if they want OP to order him a bunch of company shirts and some pants (he could get away with 3-5 pairs of the exact same khaki or black pants, no one would notice or care) and he could change in the office. It’s not a typical thing to do for your boss, but I could see it happening if the boss is an ” eccentric genius” type who lives/eats/breathes the job, and OP and COO are his right hand men who handle other tasks like getting his lunch and making his dentist appointments.

      Or, for a middle ground approach – OP could just suggest ordering a few company shirts for everyone. I’ve ordered embroidered shirts from Lands End before – they have both button up and more casual styles. I’ve also worked places where we ordered nice fitted polo/golf shirts in a wicking fabric – maybe something like that would work for the boss’s althleisure style since he could bike in it but still look decent? Or something like the pants from Betabrand that are supposed to look like dress pants but are made to bike in or to feel like yoga or sweatpants?

      I agree that this was a poor use of BCC, but if OP wants to be involved, those might be a way to help – the boss might be open to dressing up a little more daily if he doesn’t have to actually think about it, just have it magically happen.

  12. OP*

    Wow, thanks for the responses, y’all! Brief update: I did in fact bring up the bcc-ing to my boss at our weekly check-in last week (before I saw all your advice to the contrary, obviously). His response was to laugh and ask me if I liked the email. I said something kind to the effect of “I was a little embarrassed to be included on what looked like a private conversation,” and that was the end of the issue. It made me feel a little bit crazy, as I seemed to be the only person who thought this was a weird situation.

    Happy to post part of the text of the email if y’all are interested.

    1. Myrin*

      Huh? That truly is a bizarre reaction, especially asking you if you “liked” the email. I mean, what is there to like about this? It’s not like he gave you a present or something. Strange.

      I’d love to read an excerpt of the email, but obviously only if both you and Alison are comfortable with that.

      1. j-nonymous*

        I kind of interpreted that as asking if the OP agreed. Perhaps the ED has been picking up on the hints to dress up for certain meetings and knows the OP thinks the boss’s style is lacking.

    2. Random citizen*

      _Happy to post part of the text of the email if y’all are interested._

      Please do! I’m curious now that it didn’t seem to bother your boss at all.

    3. CanCan*

      I think I like your boss. Someone who is sure of himself and isn’t bothered by petty issues like dress and somebody making a big deal out of it.

      I had a boss (lawyer) who didn’t always dress the part. He didn’t own a suit. He wore khakis, short-sleeved shirts, and funky ties. He had funky green glasses. Sometimes he wore and old beige sweater with brown suede elbow patches. But! He really knew his stuff. His solutions were creative. He didn’t bore clients. He didn’t act superior to them (like many lawyers do). He listened to them (so that he knew not just what they wanted, but why – and could advise them on alternatives to their What). He didn’t drown people in paperwork whenever possible. And he was referred clients right left and centre – by his old clients, realtors, accountants, etc. The clothing worked perfectly to show (truthfully) that: he didn’t need to impress you with his appearance – his work would speak for itself; and he didn’t need to overcharge clients to support a lavish lifestyle.

  13. pony tailed wonder*

    I work at a university was asked to talk to a student assistant (SA1) by one of my student assistants(SA2) years ago about SA1’s wearing Hanes style white t-shirts without a bra to work every day. SA2 was upset that all the guys would sing SA1’s praises. I refused to talk to SA2 or go to SA2’s boss. I thought that it was not my place to say anything and thought that SA2 got praise because she was great at her job. I later found out that SA2 was one of the poorest students around and she just wasn’t going to spend money on a better wardrobe when she could get 5 shirts in a pack for cheap. I was so glad that I didn’t talk to her about her clothes. I just think that if it isn’t your place to say anything, then don’t. OP, please politely tell the e-mailer to cut it out.

  14. GrumpyandSleepybutNotDopey*

    I didn’t get the impression that the blind carbon copy was sinister of the COO. Maybe more like “just wanted to make you aware that I have put this issue on the table.” It doesn’t mean that the OP has a personal stake or needs to do anything otherwise. I would just acknowledge the message and leave it there. All parties are probably slightly embarrassed – it is most likely a difficult subject to broach, but, let the COO steer, here.

  15. Lee*

    Why not have dry-cleaned suits delivered to his work?
    That way he could change if a meeting happens on the spot, gets rescheduled or he if forgets appropriate attire. He could even change out of the suit once the meetings over.

  16. Chinook*

    The bccing thing is nuts, but I like how my mother dealt with the mayor when she was on town council. The mayor was my age and tended towards wearing golf shirts and khakis. My mother had been chair of a local school board and worked on national committees as a result before running for town council, so she had a more professional concept of what someone should be wearing when representing our community. A few of the other elder councilors discussed the mayor’s casual fashion sense (he owned the local car dealership and looked like a small town salesman) and my mother decided to take matters in to her own hands. She approached the mayor after one of the meetings and recommended he have a dress shirt, tie and jacket and dress pants in his car in case he ever has to address the media. He told her that he appreciated the tip and, as luck would have it, when he had to address the national media a month later when a child went missing on one of the town paths, he no longer looked like he just stepped off the golf course when having to address a somber issue. Since then, he only wore the golf shirt to about half the meetings and rarely when he had to represent the community.

  17. moodygirl86*

    I really don’t think you need to do anything, OP, apart from telling your colleague that you don’t want her BCC’ing you like that again. I mean, your boss is an adult and presumably is aware of any negative judgments people might make about his clothing. And if he’s not bothered, then why should it bother this woman what he wears? To be honest, she sounds like a busybody.

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