Sometime ago I heard an acquaintance use the phrase "work drag" to describe another friend's professional attire (which was much more feminine than her regular not-at-work clothes). Other friends in earshot, mostly lesbians and older than me, seemed deeply familiar with the term - and at the fact that the friend in "drag" wanted to go change immediately before joining us. I got the meaning but was also fascinated by the concept - I'd never heard the work clothes conundrum described in this way.
At the time, I was privately struggling with work and interview wardrobe issues of my own. I recently wrote a post on gender codeswitching - the ways in which queer folks often must adapt their behavior to the circumstances they're in, either to protect their physical safety, or for professional or other reasons. Clothing is a substantial piece of this, since clothes play a hugely symbolic role in our social interactions. Regardless of sexuality or gender identity, everyone uses clothes to send signals to others - about what sports teams we favor, what kind of work we do, how much money we have, whether we're outdoorsy or bookish, or both. We use clothes to convey personality - an outgoing person who likes to experiment and bend the rules might wear loud, mismatched colors together. Someone who prefers to blend into the scenery might choose more muted colors. In addition to conveying information with our own clothing, we also try to gather information by observing what others are wearing. Uniforms often indicate an official role in public safety or health. People often interpret dirty or torn clothes as a sign of poverty or homelessness but the same could also mean the person has a job as a painter, carpenter, or gardener - occupations in which fancy clothes would be inappropriate.
For queer folks, clothes can simultaneously be a haven of self-expression and our worst enemy. In relation to work, I've found this to be true especially in situations where I have to dress up - interviews, fancy dinners, meetings with Important People. I'm fortunate to have a job at the moment where relatively casual attire is the norm - jeans or slacks and a button-down shirt fits the bill for pretty much any day.
Dressing up is another story. I don't mind it - and have actually come to enjoy it - when I'm dressing up for an affair with good friends. They get me and aren't usually surprised when I show up in a tie or the like. At a fancy work event, or worse, at an interview, what to wear requires a delicate calculus. A couple of years ago, when I was applying for full-time permanent positions in earnest, I spent a lot of time agonizing over how out I wanted to be when going in for an interview. I'm always out in the sense that I don't hesitate to refer to my partner and I don't purposefully hide things, but clothing also conveys a certain message. If I go to an interview in a men's suit and tie, that's a very different way of being "out," especially in terms of gender identity than going to an interview wearing a more gender-ambiguous outfit.
I don't think this is an issue with simple answers - it's part of the world queer and gender-non-conforming folks must navigate. For those of us who feel we're at a crossroads or identities, there are few places where the gender binary becomes more obvious than when it's time to dress up in nice clothes. My partner is an attorney and has found that some judges are very particular about this. Some essentially require female attorneys to wear skirt suits in their courtrooms (rather than pantsuits). I've never worn a women's pantsuit and imagine I'd be fairly uncomfortable in one. But a skirt suit? No way. I don't know what I'd do in a profession like that. Where do those of us in the middle fit? If a skirt is "dressy" for women and suits are "dressy" for men, what about the rest of us? Who gets to be told they look nice? So much of that is gendered. When we're surrounded by other queer folks, it's easier. In the wider world, not so much.