How is it wrong to crossdress?

Answer 1

It all depends. Women can wear mannish apparel such as Trench Coats-with a tight Garrison belt accenting their figure, no problem, same with Levis, t-shirts and for a time in the thirties it was downright Chic for women to wear men"s shirts (not merely Middie Blouses) and ties. but if a Guy dons female garb- he is in the hoosegow before the nail polish is dry on his fingers, it is an odd paradox.

Answer:

Society sees women as the weaker and less important sex. For a woman to try to "increase her status or class" is considered both a good thing and an understandable, but for a man to 'lower' himself to the 'level of a woman' is below him and not something that makes sense. This leads to an attitude by women that any man who wears women's clothes must be gay or trying to become a woman. I say by women because men will follow what women do*, it's up to women to see and show that clothing has nothing to do with what or who you are.

* If women suddenly told men they had to wear pantyhose, bra's and teddies to get sex of any kind, within 3 months, maybe less, all men would gladly be wearing any piece of women's clothing that was 'required.'