15th September 2011 23:20
For the most part, you need to start developing that confidence. Some girls strongly like that in guys, so once you've got that down, you can get almost any chick.
It depends on the girl, but she probably won't care about your shoes and whatnot. Just approach her at the right moment, strike a small conversation and go from there. If the first encounter goes astray, try again, and again and again for more experience. It helps if you know what you're doing.