be yourself and dress for success...most of the "cool" kids from when i was a kid ended up as druggies, drunks, are working for the nerds.
dress what makes you feel comfortable.... don't try to be something else.
Why care about the image that other people have about you? It is irrelevant. Develop your own style. Whatever makes you happy and feels good on you. "Cool" is an ambiguous term. What I consider to be cool is not the same as what you do. Be yourself.
I wear clothes that fits my style and are comfortable.