If a beautiful "womanly" (as in, long hair, boobs, slim waist) woman sang in a manly-looking tux but with high heels people would just think "Oh, smart, but maybe a bit boxy for her figure," ie it would be totally unremarkable and the focus would likely be on how she was covering up her feminine assets by "dressing like a man." At most it would be seen as a poor choice of fashion.
But for a clearly "manly" (ie bearded) man to dress like a woman, and show off a "womanly" figure is "brave" and remarkable. Why?
Because IMO women are lesser beings. The markings of "woman" - tight dresses, high heels, make up - mark you out as being of that lesser group. For a man to wear those marking is beneath his dignity - he is opening himself up to ridicule. He has come down off his manly pedestal and is wearing the clownish gear of the silly female.
For me a man wearing women's clothes and expecting adulation and praise for it is like a monarch digging a ditch and expecting to be seen as oh so benevolent and "down with the people." Playing at being a certain person and expecting recognition for it is incredibly patronising to that person.
Women have no choice in being women. We don't get recognition for wearing make up and tight dresses, in fact it's just expected and if we don't do it, then we're "frumpy" and "letting ourselves go." We dig ditches for a living, so to speak, and for someone to take time out of their privileged life to "join in" in an oh-so-jolly way (but still while wearing their crown beard, so everyone is aware they're not actually a lowly ditch-digger) is fucking annoying.