During the fall and winter I wear jeans, usually with a button-up and/or sweater/cardigan, with a plain t-shirt underneath. I rarely wear jackets, mostly because they're a hastle to take off and on every time I go insides and outside.
During the summer, it's simple. T-shirt, cargo shorts, and van's or flip flops. Pretty much every day.
A mixture of preppy/urban. I get compliments a lot on my sense of style. Urban Outfitters is where it's at. I often mix **** together and still come out fly.
I causally dress similar to that. But nothing too metrosexual.
I'd probably wear those shorts... If not for some personal reasons. Kids at my school pretty much expect it.
But on that guy specifically, they do not look too good.