Bullish Q&A: Should I Step Up My Wardrobe to Succeed at Work?

Should I Step Up My Wardrobe to Succeed at Work-

Hi Jen! My question is about the importance of office attire and appearance at work. I work at a company where the dress code is very casual. Most days I just wear jeans and sometimes dresses, but I don’t wear much makeup and usually put my hair in a bun. Recently, however, I was promoted to a more senior position and have found myself in more and more meetings with higher-ups. Most of them are much-older men and many don’t dress casually every day even though they can (they usually wear slacks, dress shoes, and button downs, no ties except for special occasions). I like dressing casually and feel it suits my personal style better than a business casual wardrobe would, but I’m beginning to feel that I just don’t seem as professional as my colleagues with whom I’m finding myself in meetings, even though my clothes are always well within our dress code. Do you think it would make a big difference in my career trajectory at this organization if I ignored the casual dress code like these guys do, and stepped it up a few notches? And what do you think about the makeup thing? I find myself a little indignant that women are expected to wake up earlier to take time out of their mornings to put on makeup and do their hair while men aren’t; I also just hate waking up early so maybe I’m looking for excuses not to.


Yes, I definitely think you should take your clothing up a notch or two. “Dress for the job you wish you had,” etc.

You can do this and still be comfortable (although not as fun, if fun is your thing). Look at what you’re wearing now. What if it were the same, but mostly navy and gray? If you have some kind of white shirt and some kind of navy or gray thing over that and also on your bottom half, you now look more conservative. (Does that seem like the way to go at your company?) Try some stud earrings.

Here’s a pic of me with MOGUL CEO Tiffany Pham. I’m wearing navy corduroys, the most underrated of pants and looking fairly businesslike because of the navy-on-white thing. The blazer is silk and looks dressed up without being stiff or uncomfortable. (I call that half-ponytail my “math genius” look.) This was just an average day when I got dressed in a hurry. I would feel completely comfortable meeting with stuffy old dudes in this outfit.


I don’t think you have to wear makeup. I think people (some people, not the good kind) sometimes react badly to women without makeup because some of those women are seen as failing to perform any femininity whatsoever, and if you stop doing femininity, you’re obviously an anarchist who wants to blow up the government. (Real anarchists mostly do not want to blow up the government.) One pair of little pearl earrings, though, and you’ve satisfied that bullshit requirement, with little time or discomfort, if you feel comfortable with that.

(As a side note, here’s an article for people who are super not willing to do that, or who want to do that but society tells them not to, or a variety of other difficult situations: Genderqueer in the Office? A Few Thoughts on Building a Career.)

Or sometimes the issue with not wearing makeup is that you look too young. If you actually can be mistaken for a teenager, that’s usually easy to fix with more professional clothing styles, or a good haircut, or a pair of glasses.

Not wearing makeup can also look a little weird if your clothes are very dramatic and feminine. If you are wearing a full-on skirt suit (maybe with a peplum!) and a pair of pumps, it does look a little weird not to wear makeup. But if you are wearing neutrals and a really artsy necklace — like a long pendant with an antique clock hanging from it — you can do that Brooklyn/San Francisco “maker culture” look, where no one expects eyeliner (or pumps).


When I was teaching the GMAT, I sometimes affected a look I call “super intense genius physicist!”, which involved button-down shirts, ultra-long hair, no makeup, and PROMINENT GLASSES. Fun story, when the Margaret Farquhar episode of The Wonder Years aired (here, scroll down to #4), people at school called me Margaret for months.

Personally, I find that a bold pair of glasses and a five-second swipe of lipstick are more than enough stuff on my face for most occasions. I don’t have time for blowdry rituals or eyeliner either.

Finally: Just get a good blazer and keep it in the office, on the back of your chair. (A lot of mine are BCBG Max Azria.) Put it on top of whatever you’re wearing every time you have a meeting, meet someone, etc.

I picked up this tip from a very old book: John T. Molloy’s New Women’s Dress for Success. This book is twenty years old (the original was actually from 1977!), but the thing I liked very much about it was that it was research-driven. Molloy took photos of the same woman with and without a blazer (for example), and asked people to guess her job. Or in one study, a woman employee was asked to go to another department while the boss was out for lunch, and request a document from an administrative assistant. Women in certain outfits got the document; others didn’t. (Suits and separates worked better than dresses, but a dress with a blazer over it was much better than without.)

I can’t imagine how many of the specific fashion suggestions (about which Molloy was often apologetic!) would hold today, although a lot of people in positions of power are plenty old enough to still have 20-year-old views about women and women’s clothing. Personally, I learned a lot about natural fibers and “traditional business colors” from this book. And, obviously, blazers. If you were actually going to read this ancient old book, I might make it into a drinking game – for instance, drink every time you read about “traditional business colors.”

Of course, many self-employed people count “dressing however I want” as a perk of the job. And if your work is very valuable to others – especially if it makes money for a company in a very direct way – you can get a lot more leeway to do what you want. But if career advancement in your current field is the goal, there are relatively easy and painless ways to do that. You might even start to enjoy looking like (someone’s idea of) a boss.

Also see: Social Class in the Office


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