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.
Find Your Style, and Stick to it