I never wear jeans anymore, haven't since i was 12-13, now is just khakis/chinos. I never wear plain t-shirts really, usually a button down with a white undershirt and sleeves 3/4 rolled up, in the summer, pastel shorts and button downs or tanks, I wear nike mid-calf socks exclusively (They feel and fit nice). I care a lot about how I dress even though some people might have a differing opinion. If you dress nice, you go far in life. I also wear vans/polo lowcuts and sometimes my sperrys (both boat shoe and mid-tops).
Don't really know how you would describe it, Frat I guess would be close, I've also heard rich white kid, but I tend to ignore that statement.