I don't think, it's a problem. Depends on a girls sexuality. I'd go on a date with you ^^ I think, crossdresding is cute and if someone looks more androgynous, it can be really attractive. Nothing to be ashamed of.
I have no issue if that is what he likes, but I am very much into men who are completely masculine. I'm not attracted to men who would dress in women's clothing because I am not attracted to femininity.
I have a friend who cross dresses. Nicest guy you would ever meet married with kids & completely straight. My advice is keep it to yourself unless you are completely sure of how friends or wife will react. My friends marriage almost came to an end when he told his wife.