In direct contradiction to Pythos, I have to say that we do live in a gender binary world and I don't see it disappearing, no matter how much we, as members of this community, (which I also consider myself a part of through my association with my SO), would wish it were otherwise.
If the gender divide were caused by an overly strict and stereotypical gender socialization mechanism and if it did not sit well with most of these male-socialized men, believe me there would be a much greater segment of the male population wishing to break free from it in adulthood. The internet expands everyone's choices and memberships in forums such as this one would increase 1,000 fold. And then there would be no need for them since we would all be androgynous.
Nothing will ever take away the fact that most boys want to be boys and most girls want to be girls (even if said girls wear blue jeans). It is not a stupid notion. It is simply a fact of life.
The best we can hope for is a broader recognition and acceptance of gender and sexual diversity, which can only be achieved through more research, media exposure, changing laws, and widespread education. But if or when this should ever happen, I seriously doubt it will make the testosterone laden men want to wear skirts as a fashion statement, although perhaps a few men who are more on the culturally creative edge might want to wear them to keep cool in the summer.
And if perchance skirts were to find their way into the mainstream, there would be just as great a difference between male and female styles as to make guys want to not wear the girly skirts that M2F TGs would continue to want to wear. The gender fashion divide would be the same as it is now, even though fashion will have continued it's evolution process as it always has.