One of my favorite bloggers, Figleaf, of Real Adult Sex, posts on the problem with crossdressing: (it’s an older post but worth reading)
I don’t have a problem with cross-dressing per se. Whatever blows up your skirt, as my mother-in-law sometimes says. The couple of times I’ve tried it were interesting enough. It’s just that… well, it’s just that… women’s-cut clothes rarely look very good on men.
Case in point, check out this photo of former New York Mayor (and current Republican Presidential candidate) Rudolph Giuliani.
They took a bunch of women’s clothes that would fit him at the broadest point — his shoulders — and then padded the rest of him to fill in all the spaces women go but men don’t. Then they stuck a wig on him, which is fine I suppose, but then they threw on a bunch of make-up using patterns that might accentuate the geometry of the average woman’s face but kind of conflicts with Giulianis geometry.
Net effect? He’s not dressed *like* a woman, he’s dressing *as if* he really was a woman. It’s an unsuccessful deception.