There's no debate...everything is a question of style, to each his own. (not talking about the "no style" guys that don't give a shit about clothes, no hate, they must have their reasons)
Some people wear sized up or loose jeans and it looks perfectly ok, others wear them fitted and it looks perfectly ok.
Some girls don't even care about how a guy is dressed, others do and they can have a preference for a style...that's all, as I myself have my preferences about how girls dress even if it's not determining.
I went through skater style when I was in highschool : oversized baggys, loose tees, skate shoes and stuff...girls liked my style ;) ...well at least the ones that were onto that style.
Then I made a crappy transition, when I look back, I was dressing like crap...
Now I think i'm starting to settle on something and i'm happy with it.