| For your teeth, gauge it once the braces come off. If they're off color, then go for it, because you're going to want to flaunt those bad boys once the shackles come off... However, I'd start slow and go to the drug store and pick up a nice whitening toothpaste first. Go for the professional thing if the toothpaste doesn't do the trick.
For the clothes, medium sounds right, but that depends on your style and the store (Boss medium is much slimmer than Hilfiger, etc.). Slim fitting is typically what you want though - if you need help finding what the right fit is for you, bring a female friend/relative with good taste along with you until you are able to gauge for yourself. Fit is probably the most important aspect of style - a guy wearing a well-fit $20 shirt will look better than some fool wearing a baggy or over-tight $200 shirt.
As for your question of wearing polo and other "nicer" shirts, the answer is yes, these look better. However, this really goes for all the style questions I've seen on this site: it's more important that your clothes have a consistent style that matches the image you want to present than whether or not you should sport any specific style. For instance, with my style (GQ casual) and image, I'd look pretty ridiculous sporting Affliction or the sort, as much as I like some of that stuff. Think of a personal style that you like and you want to go with (preppy, athletic, GQ, etc.), and start buying items that align you with that style. No matter what though, just make sure that the fit is good, the colors match, and that they are in line with YOU - dressing GQ doesn't work if you've got terrible posture, you stink, and are generally not a "gentleman".
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