I've heard an easy cure for acne is just to sleep with a clean towel over your pillow at night. Not sure the actual accuracy of this since my skin is totally clear.
As for your actual look, just find what suits you. One idea would be to grow your hair out long and they cut it/style it in tons of different ways until you find a way that you like. You will need to be ready to use product every day, but if its what you want, you might need it. What I have noticed with people is that once they have a set hair-style, the rest of their appearance just naturally sets into place. I mean if you have absolutely no clue on how to dress correctly, that will be a problem, but if you have some competency you should be fine. Like as for me, I usually just wear a plaid shirt with jeans and I'm sexy as fuck.