I'm going to assume not many of us MMOGers here wear urban clothing, but here's a great site for just that:
DrJays.com Urban Clothing: Akademiks, Apple Bottoms, LRG, Ecko, Rocawear, Sean John, Pastry, Baby Phat, Coogi, Dereon
This is my favorite place to shop online, as you can get up to 70% off on brand name clothes (Adidas, Timberland, Avirex, Rocawear, etc). Over the past two years, I've dropped over $3,000 worth of clothes on the site. Love the place, and I don't see myself shopping for clothes anywhere else (minus the few odd times I see a nice shirt in a mall).
EDIT: Ew, massive date gap between this and the last post. Oh well, topic is stickied anyway.