So.. I'm pretty active on Facebook and in our local LA community and I talk to a lot of crossdressers that are new to this, or go out very rarely, or are entirely closeted. And I often hear the sentiment that crossdressing is "unfair." As in women can wear things like jeans and men's button-up shirts, but men can't wear dresses and skirts.
I've thought a lot about this topic and I feel that it's a false equivalence for a few reasons:
1) There is a big difference between a woman wearing women's jeans and a woman wearing a three-piece suit and tie, using makeup to simulate forehead wrinkles and beard shadow, and giving herself a male name like "Steve." Crossdressers and genderfluid folks are clearly doing the female thing to a radically larger degree.
2) The clothing dichotomy is rooted in gender roles. From an early age, girls are praised for their appearance. Boys are praised for their accomplishments. It makes sense that women would have a radically larger pool of wardrobe choices, as their visual presentation is so much more important than a man's. It's a lot more work and expense too.
3) I believe that women don't "crossdress" in the same way that men do because they already have the ability to express themselves in wider scope than the traditional man. It's not necessary for them to inhabit a male persona to be "badass".. they can just do that as a female. Many people in our community (me included) are yearning to express a softer and more sensitive side.. and we find it easier to do within an entirely femme persona.
4) Point #3 is not to say that women have it easier and are more free. Quite the opposite. I think that women have this freedom because society still values them less and sees them as more frivolous than a man. If a grown woman wants to be girly and paint her nails with glitter and dance and cry, it's no big deal. If a man does that.. people freak out.. because he's supposed to be in charge of things.
Just some thoughts. I've been at this for about two years, and it's really given me a lot of perspective on how women are perceived and treated.. especially as I've gotten better and more serious at presenting female.