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What worked for me...
Join a gym, or exercise a lot. I don't have a clue what you look like or anything but it isn't really about looks. You just feel better and more confident when you're in good shape/fit - or at least, I do. However you look at the moment, you'll probably look better after exercise.
Henry Rollins had a decent piece about how weightlifting gave him confidence. I'm not talking about weightlifting as such, but lifting weights, exercising regularly and eating the right foods made a massive difference to my confidence and my outlook on things in general. I do believe the benefits of exercise are more than just physical -- I'm in a better place mentally too now.
Good luck, anyway!
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