Depends.
I'm a gay male, yet I wear girl clothes. (Nothing too girly though, just jeans, sweatshirts, sweaters, t-shirts [not the really girly ones], and even belly shirts, like basic apparel) Like the things I wear could pass for guy clothes. (Other than the belly shirts of course

)
But guys in skirts + dresses, wigs or whatever just weirds me out a little.