'I'm not ashamed to dress "like a woman" because I don't think it's shameful to be a woman.' - Iggy Pop
So there's reason #1: men who dress as women don't hate women. They just don't.
Aesthetically it's fun. It trips up your expectations of beauty, it makes you question what you find beautiful about a man, about a woman. It trips up your notions of what a man or a woman is, where the lines are drawn (hint: there aren't any. If there are, you're exploring a map, not a country).
Cross-dressing requires a lot of courage, because women are second-rate citizens, and anyone who may deviate from the "normal" hetero sex model is also a second-rate citizen. A man who chooses to dress as a woman - even in a small way - will provoke a special layer of hatred in some men, and some women. Likewise a woman who is uppity enough to dress or behave like a man receives a particularly bitter type of abuse. You don't get any chicken-hearted transvestites or genderfuckers. Those guys and gals know how to handle themselves, whether that's a sharp tongue or a smack in the mouth. If you want to break them, you'd better have brought a tank.
AND
anyone who lives on the fringe, who isn't dead centre "normal" and who has suffered the slings and arrows of outraged Daily Mail readers, often develops a layer of humour and self-knowledge which is generous, which is not precious or defensive, which is comfortable with itself, not delicate... not about putting people down. There's an acceptance of self and therefore an acceptance of other people's weirdnesses.
As a weird creature, I need that open heart like roast turkey needs gravy.
AND
what IS "sexy"? Is it the shape of someone's body? Or what they're wearing? For me, it's the knowledge that inside someone is a cathedral of variety, creativity, depth, myths, a sense of theatre and fun, and that gives me licence to be all that I am with that person. Not just how I look or sound or seem, but all the other stuff (and there is a lot of me). I don't necessarily mean cross dressing. I'm as happy for you to be a bird comma aves, as a bird comma at a bus stop. Let's not limit ourselves, here.
AND
because I like my genders and sex roles bent. I like them blurred, smudgy, ill-defined, transgressional, subversive, iconoclastic, idiosyncratic, provocative, a little bit "fuck you", a little bit "come on in and try it", playful, confident, expansive. The first thing people notice about me when they meet me is how very female I am. And I'm not. It squashes me into a role I'm not suited to. I'm a gender bender trapped in a very female shaped body. I wouldn't be one iota different as a person if I'd been born with a cock.
What's really fun about that is that most straight guys who know me well kind of dig that about me, and kind of dig how it affects them, because it's very freeing.
So let me share a few beautiful men and one beautiful woman with you:
^ Jude Law, John Leguizamo, both utterly stunning.
^ Rufus Sewell - I mean, seriously, LOOK.
^ OMGOMGOMG Heather Cassils.