I think it's pretty simple, some people can pull of some looks, some people can't.
Of course men can wear eyeliner, on some it will look great, for others they'll just look tragic. Some guys can wear what are considered to be womens clothes and still look good, and some can't.
It really just depends on your body shape. It's true that alot of guys look ridiculous in a holter top, but then again, so do alot of women.
Actually, mens shoes with heels have been supposedly comming into fashion for the past few years, which I think can look really good aswell.
Oh, and for every man who looks 'gay', there's just as many women who look butch.