I don't know man you seem to have the kind of complexion where I didn't really have much of a problem with any of the shirts but I'm not a huge expert.

As far as the hair, long is good but I would get it layered or change up the style just a little bit. When I was in middle and high school I was very self conscious of my big nose and big ears then with time I realized as long as I wear them with pride no one really cares let alone myself anymore. So yes I would layer it up a bit, expose some ear, a little more forehead and you would have yourself a bronze achilles do.

The fit on the t-shirts is golden. The long sleeved shirts and the sweaters seem a little large but I dont' blame you.

And not that it matters but another note, I'd have to say the DBs look best on you. The converse too generic and the vans too immature, but my are those DBs good on you, even with just jeans and t-shirt.