Wear what makes you feel good than look good. Or set up a wardrobe of clothes that covers both quality, so there wouldn't be any noticeable bias. I know that's an easy say but it's the best I can come up with. :)
Oh my god this is a 2012 post...
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.