overdressed / underdressed

A reader writes:

So I just started a new job last week. All my co-workers come to work in jeans and sweaters for the most part. Every now and then someone will wear a nice dress or a suit. I wear nice dresses and skirts nearly every day and get compliments from my co-workers.

Yesterday I heard my boss tell my other boss that I overdress. Upon hearing this, I dressed down today and put my long hair into a pony tail. I looked like all the others. One of the two bosses I mentioned came in today and said, “She looks bad. Don’t invite her to the meeting with X company today. I don’t want them to think that people who look like that work here.” What’s up with that ?

Either (a) your boss is ridiculous, rude, and petty, or (b) you dressed down too far without realizing it.

I’d just handle it head-on. Say to your boss, “I know this may sound silly, but I’m not sure I’m figuring out the dress code correctly. Is there anything I should be doing differently?”

But then I’m a confronter. What do others think?

{ 12 comments… read them below }

  1. Lisa*

    Go for it, give him the benefit of the doubt. Maybe you dressed a little too down for that particular day. See what you get. How does your boss dress? His peers?

  2. Rachel - I Hate HR*

    Wear what you’re comfortable in. Don’t go out and buy a new wardrobe just to fit in.

    I still wouldn’t wear jeans. But maybe instead of a suit wear dress pants with a more casual sweater.

  3. Anonymous*

    Thanks for the comments everyone. My boss actually parades around the office in shorts and flip flops at times which is why his remark is even more uncalled for. He is a high fashion designer and a bit of a diva.

  4. Tracy Tran*

    On your first week, always overdress, even for casual Friday. Have a feel of what your company does. In your first week, you’re trying to build a chemistry and cohesion, know the tells like a poker player.

    On the second week, if you’re still uncomfortable, do it again until you get most of the system. If you get it, then you can do whatever you want. Of course, don’t go too happy.

  5. Anonymous*

    I went through something similar once. I work in a similarly casual office in the arts. About 2 years ago, wanting to get noticed by the higher-ups I started dressing just a notch above everyone else.

    At first, there were some comments, most were joking, I know there were a few whispers from detractors. But because I just stuck with it, everyone stopped caring and moved on to other things. And when a client comes in, I am always called on because they know I will look professional.

    It’s early in your time at this place, so I would say, if you feel most appropriately professional in dresses and skirts, do it. You will also probably find yourself dressing them down just a little here and there after some time and the difference won’t be so dramatic.

    But here are some other questions to consider: Is “overdress” possibly code for something else? Dressing a little too sexy? Or maybe too dowdy for your particular field? You say your boss is a high fashion diva, how much does style matter in your field of work? (are you in design, fashion, arts, music, pr, or any other similar field?)

    The rec from anonymous to see what the women a rank or two ahead of you are wearing is the best advice, assuming of course at this place women are in those positions.

  6. almostgotit*

    If it’s important enough for all this running commentary by the bosses, and now you, it’s important enough to find out about. By asking.

  7. Julie O'Malley*

    I would have assumed that the boss was pulling my leg. If it’s a shorts and flip-flops kind of workplace, it doesn’t make sense that dressing like everyone else would truly be an issue.

  8. Sarah*

    How is it that you ‘overheard’ two different conversations about you? Do these bosses make a habit of talking about employees where they can be easily overheard? That is rude.

    Both of those comments were inappropriate. What is wrong with overdressing if you are comfortable? If it isn’t shiny or too revealing, it should be fine.

  9. Deepa Subbaraman*

    As someone who always dresses upat work, i would suggest the following :

    1) Ask HR/the BOSS if there is a company policy on DRESS CODE. Also discuss what is the impression we want to make as a company when we have customers/visitors etc.

    2) Dressing up or down would depend on the industry/company you work for. In case you work for say a CASUALS garment manufacturer then Dressing up might at times alienate against other colleagues esp. if they are not of the same opinion/. Casual Chique is also a fashion statement depending on the industry you work for.

    3) Would certainly want to know how did you overhear the bosses? If it was in passing/or was it informed by another colleague who overheard. if its the latter, perhaps you might want to take it with a pinch of salt and DRESS UP instead

    Last but not least, when in doubt just remember that dressing u, does create a good first impression/foot in the door for customer meetings etc.

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