Move to Berkeley where you can scavenge 4 thrift stores within a 0.5 mile radius and get all the cool stuff for cheap.

Sounds like you have a pretty good idea how to shop: buy what you're "feeling." It won't matter how stylish your clothes look if you're not comfortable sporting them, ya dig? I know what you mean about vans, which are in my opinion the perfect shoes - they have become somewhat mass produced and can look pretty high school. Of course, you're in high school but I know what you're trying to do Ace. Vans recently collaborated with Marc Jacobs (pretty high fashion, all the dumb sluts like him), and churned out some sweet limited editions. Just make sure to get enough talc powder if you're going to go the whole sockless route, which is very "in" these days.

In my opinion, the backbone of style is function. First, make sure it fits, like a canvas on a frame. Than you can begin to paint.