I think it's cool, I follow many androgynous makeup bloggers with their how-to videos and everything and they're more beautiful than most girls I see.
But the problem in crossplay rather than actual crossdressing is, and no offense, not many men (that I've seen) correctly do makeup and hair. Not that it's big or anything as ANYONE can apply a little makeup, I feel like some male crossplayers just need to look up a few tutorials and such. But that's only in cosplay, at least from what I've seen where issues like that arise.
My favorite though, is seeing boys in Lolita. Men tend to have different face shapes (I said "tend"), from girls, so seeing them wear Lolita, with the beautiful split wigs, when done correctly just looks gorgeous!
And I don't know if this was the question being asked but just throwing it out there, I think it would be sweet to date a cross dresser, whether they be male or female. I'm neither gay nor straight (dafuq am I? Nobody knows) but it all sounds pretty cool to me!
Now as I said, and don't think I'm being MEAN or anything, but as I said earlier, quite a few male crossplayers just don't know how to correctly apply makeup and/or work with hair/wigs. BUT there are some BEAUTIFUL, kind-hearted people out there who have more than enough tutorials!
I love Michael James and the group channel called "androgenetics". If you haven't heard of Michael or the AndroGenetics group themselves, I suggest checking them out. They're all really nice people.
I can't swag understand swag your accent