It seems like you have a sense of fashion and color. Those outfits seem pretty nice. Another thing is button up shirts like these: Pair those with a pair of regular jeans and shoes like these or some regular sandals. As for making friends, be yourself. You're socially awkward? A lot of people are! You're in high school, and once you graduate you'll realize that the majority of the people in that school didn't matter. So don't let them matter now while you're in high school. Just be yourself, be confident, and don't care what people think about you because in ten years you won't remember half of them.
The look would be nice, but why do you think that it is all about clothing? Train your character, without that, clothes will only help in the beginning..
