Financial talk

I am not really the best fashion type guy around so I really need some people to help me. I going to get a job soon so that I can afford it. I'm dark skinned if that helps. I like to wear jeans with button down shirts a lot but I think it's hot when guys wear them with the sleeves up a little but I don't think it looks right on me. I like to wear jeans and then a vest or sweater and shirt. I also love the Abercrombie, AE, Hollister type clothes. Do you think it will look funny because I'm black? Since it's going to be summer, I want to get some shorts and polos and T's to wear but I always think that I look funny. I really like them but should I still wear them? I also need some nice watches and sun glasses. Money really isn't a problem and of course I would love to look like I had tons of money, who wouldn't? Any tips suggestion links or whatever would be greatly appreciated. btw I'm 16 and a little gay.