Wearing a dress for the first time was really liberating. Not, mind you, because I have longed to express a suppressed aspect of my gender of sexuality. It's just that my ass really enjoyed the breeze. I was also wearing it in a very safe place - the home of a queer friend where everybody, male, female or otherwise, was raiding her closet and trying on all of her (unbelievably fabulous) clothes. In fact, the outfit I bought today is for a party at her house as well. I can't say that I'd necessarily be comfortable wearing it anywhere else, even most queer spaces.
Now I ask you, what the fuck is that? I mean, yes, some of that is probably self-censorship and a lack of daring, but as much as I wouldn't be ostracized (too much or loudly) in a gay bar for that, I bet I wouldn't get picked up either. Let me tell you, though, I may look even hotter in a dress than whatever gender-role-conforming clothing I'd usually wear. For example, my chest hair is shown of beautifully in a strapless halter, and as nice as my legs look in cargo shorts, I think that a tulle skirt provides a lovely contrast to my super cut calf muscles. So the question is, if dresses are comfotable and look good on me, why don't I generally want to wear them? Well for one thing, a lot of the times we forget the whole blessing of being queer men and instead of challenging gender binary, partriarcy, misogyny and instead think of ourselves basically as the same as straight guys only we put our dicks elsewhere and are somewhat more likely, on average, to have a substantial knowledge of musical theater.
However much I reject gender binary in actions and am as happy to tell people that I bake cupcakes as I am to say I played rugby is college, dressing outside of gender normitive clothing takes examining my gender and my gender in relation to a society one layer deeper, to a place that's finally a little bit edgy for me. Possibly it's because I don't have any role models for men in dresses. I don't want to be a drag queen, it's not a sexual fetish as in transvestism, and I'm not doing it as part of a skit or pagent. I'd be one of the only guys out there saying, yep, I'm a dude, "I'm not trans, not a drag queen, don't get off on this (sidenote: all lovely and legit reasons for a man to wear a dress, just not my reason); I'm just a hot guy who wants to wear a dress today because after a number of decades I'm simply over pants at the moment."
However, I think the question is much bigger than me wearing a dress or not. The fact that doing so would, indeed, incite some level of discomfort, mocking and possible assault means that we are still, as a culture, so locked into a strict binary gender with assigned roles and costumes that our reaction to obvious deviations is tends to be swift and negative. So while I'm not so worried that I will be inconvenienced changing into my dress once I arrive at the party, I do worry for kids and people of all ages, queer and not queer, who are hiding pieces of their soul and failing to reach their full potential becuase some dream of theirs is gender nonconformist. I want to wear my dress right down Market Street at noon (OK, maybe 3 when the school buses are out) just so more girls will end up in engineering programs and boys will take up ballet. I want to. But it's fucking scary.