Eh. A skirt is a short tube of cloth. A dress is a long tube of cloth. Pants are two long tubes of cloth stuck together. Of all the many, many completely insane, imaginary prejudices humans love to throw at each other, "improper" clothing to me is one of the most ridiculous. It means nothing at all. Ironically, the people most vocally against it are being far more stereotypically girly, obsessed as they are over the correct fashion people should wear. It's not harming anyone, so do as you like. If the annoyance of reactions from others outweighs the benefits, then stop doing it.
What I'm trying to say is, there seems to be absolutely no actual advantage to "expressing yourself" and wearing what you want or acting how you want, but a laundry list of disadvantages. Which makes me continuously wonder, why do it? Sure, in the privacy of your own home it's fine. But why in public? There's no benefit to doing it in public. So I just don't understand why people still do it.
Reducing self-loathing can be a pretty substantial advantage. Are the foolish gawks and eye-rolls of strangers that much worse than constantly having to lie about who you are? It's up to the individual where the balance is, and if it puts them in actual danger, they often won't do it. Even then, sometimes they do, what with the whole "when good men do nothing" saying. If nobody makes any effort to defy prejudice, it's not going to go away anytime soon, and even those who are more accepting are likely to just turn a blind eye and pretend there's no problem if the problem doesn't make itself known. In lesser, everyday cases, though, if you're actively avoiding doing something you want to do, odds are good you're actively doing something you
don't want to, all the time. The advantage of changing that seems obvious to me.