If you have a cool look, it doesn't matter how expensive your clothes are. Find your own personal style and stick to it. Maybe a grey pocket tee, chinos, and simple sneakers are definitively you, and that's OK. You won't have to take stupid style risks and spend a bunch of wasted money just finding who "you" really are. Don't be afraid to look cool, but once you find what works: play that record until it skips. Your wallet will thank you, and now, you can focus on the things that really matter, like having fun.