Urgh, I have a male friend who works at General Pants, he's such a fashion pony. He's all customized jeans and 'I braided my hair' and ksubi whore and geh. It's not attractive, it's just too metro to be manly.
I do have another friend, however, who is the most coolly dressed boy I know. I think the difference is that he's well-dressed, he's fashionable, he's just not trendy. He still looks like a guy. And it's damn attractive. I don't know how he pulls it off, but he can pull it off, if any of the other guys I know wore what he did they'd look stupid, but he's just cool.