Sara, I see many men who look terrible in male clothing. It helps not to have a beer belly or be obese. Same with women. You're correct the vast majority of women are going to want their husbands/boyfriends to fit the masculine mold, even if they are obese and not picture perfect.
When it comes to men emulating women not all men strike out. I have to assume many of those terrific looking crossdressers on YouTube are in fact men wearing women's clothing. If not, they sure fool me. Maybe the problem is men are not adept at presenting the illusion. Even on this site the critical eye is already aware the person is a male emulating a woman. That being said, I still think many are wearing their female attire well. Even better than many women I know.
I don't see the day when the women's section is going to be full of men buying dresses to wear. I believe one has to be born with that mindset and not suppressing it to conform to societal norms and expectations. All that being said, as I stated in other threads, there have been women's clothing stores in my immediate area which openly solicit patronage of cross dressers.
