My judgment is your judgment is flawed. According to you men should feel free to wear dresses and high heels, what's the difference it's just clothes. My eyes are rolling out of my head here!
I wear jeans and boots all the time. In fact - I wear jeans and boots without losing femininity while I do it. How do I manage? What makes my jeans and boots different than my husband's jeans and boots? Color and a tailored fit.
When men think of wearing 'dresses' people usually think of doling up the feminine factor: dresses made for women showing cleavage, some skin at the waist, a cut for a feminine figure. . . and everything is extremely feminine: makeup - heels and all. This is what guys in the US think of when it comes to a 'dress' . . . If I were to try to dress up like a man I wouldn't wear clothing made to fit a woman or look femine.
So - when I wear boots and jeans to work on the house they're made for my female figure. They might have some pink or blue - but overall they're utility and serve a purpose: to get dirty without getting completely trashed while allowing me to climb around, do heavy yardwork and crawl around under the house doing plumbing. They serve the same purpose = men wear these clothes for that same purpose. For me I have extra things to fuss over: I can't have my boobs dragging on the sewage strewn crawlspace floor - for example - and if I'm wearing a regular bra they're too 'out there' in the way.
So: to the American Male mind: if a man 'wears a dress' he's trying to look like a female. But men all over the world wear 'dresses' - they're in the form of cultural clothing like kilts and thawbs (the traditional, long white 'dress' that men wear in some areas of the Middle East)
Men do not have to be feminine to wear 'a dress' - it makes sense that the clothing serves a purpose - and gender-clothing is defined by colors and the way it's designed to fit.
I don't look at a man in Thawbs or Kilt and think he's 'gay'
I don't look at a woman wearing workboots and some work clothes to be 'a lesbian' either.
The only reason why men in the US don't wear robes and 'dresses' is because our civilian cultural history sort of erased it out of our cultural history - leaving male 'dresses' in the US to purely be a religious thing: like my Dad and his sunday 'dress' - or the choir and their 'dress' - it's not a 'feminine dress' it's a 'religious dress' and doesn't denote gender: but has a status and purpose.
Men in this country don't even dress like they use to 200 or 400 years ago. :shrug: Have you become *more* masculine or something? No - male stereotypes have become *more* rigid.