It really depends.
Wear threads that fit 'you' as a person, and that say something about yourself. For best results with the ladies, wear clothes that fit your attitude and personal style, whatever that is.
For instance, if you're pretty quiet and don't really make yourself stand out in a crowd, don't use clothes to do that. It will just make you look unnatural and won't help create that aura that you want. If you're a sporty guy, throw in some sports jerseys and stuff. You get what I'm diggin' at?
Wear clothes that fit your personality, don't wear clothes and then try to fit the personality that goes with them, it won't feel natural to you and won't create a positive vibe.
Put abit of thought into how(or if) you are unique from the average guy, and incorporate those qualities into your threads.
My personal choice would be always to stick out from the crowd, although that is my personality so it doesn't seem unnatural to other people.
Here is what I'd do for the school year:
1. Buy 2 pairs of stylish shoes(white & black)
2. Buy 2 nice belts(white and black)
3. 2 or 3 styles of jeans(destroyed, bleached, dark)
4. several collared shirts(polos)
5. as many t-shirts as you want(throw in afew nice ones with pics or band names)
6. 3 or 4 nice sweaters
7. 1 or 2 sports jerseys(i hit up the rugby jerseys)
Try to coordinate what you wear(ie. if you wear a white belt, wear the white shoes to match, if you wear the black belt...black shoes.) and make yourself look decent, you know what I'm gettin at.
THe list above is what I've done in the past, it worked for me.