I don't think there is anything wrong with the way you look, and I agree this is a confidence issue, rather than a looks issue. Regarding the clothes: just learn to dress for the occasion. It's okay to wear sportswear if you are attending a sporting event or playing a game, or even just hanging out on a Saturday morning around the house, but if you are going out anywhere else, you might want to ditch the jerseys, tennis shoes, and basketball shorts in favor of something a bit more sophisticated. And PLEASE do not wear emo clothing. You look a bit too old to dress like a Junior High kid.
I like that you seem smart and can type a coherent sentence without using text-speak. There IS a market for smart guys.
Relax... I'll need some information first. Just the basic facts - can you show me where it hurts?