For me it's pretty simple. On an average day, I'd probably be wearing something along these lines:
Jeans (not skinny, but fitted)
TOMS shoes (or flip-flops, if weather obliges)
old t-shirt (or button up long-sleeve shirt)
On hot days, shorts come into the mix (plaid yesplz)
During the winter, I tend to stick to the long-sleeve button up shirts (typically white with designs on it, club-style I guess), a light military-style jacket (fitted), jeans, warmer shoes (like my white Adio shoes since skate shoes are decently thick), a visor beanie (got one in black and one in white), and my black-gray plaid scarf.
I guess that's pretty descript, maybe I'll grab stuff later to take a pic or something... e.e