Younger chicks high school and below care. You're surrounded by competition and girls expect you to be just as dope or better than the people in your school. You don't gotta be way ahead, just "with it." As for older girls, trust me dudes, I'm around women all the time and they don't know jack shit about men's fashion; they just kinda lose touch after all the school shit. Most of them just care about a man's physical features. In fact, if they find out how hard you try to look good, they think it's gay. I've found that most older girls just like a guy who looks good but doesn't try hard with his clothing (i.e. jeans and tees).
Basically, this goes with everything in life: don't try too hard; if you make everything seem effortless you get more people attracted to you. Oh, and don't discuss clothes with women to try to show off, lol.