i'd say just all around bad ass.
brandwise, i wear alot of american apparel, diesel jeans, levis type ones,  cheap monday jeans, alot of polos from various labels, alot of local screen print artist shirts, vintage "cowboy" shirts, band shirts, lots of "urban outfitter" type clothing, but generally not from urban outfitters, some boardshorts. shoewise, several pairs of flipflops, i have some crazy pairs of airforce ones and dunks,  some onitsuka tigers, creative recreations, some chuck taylor lows, i have two pairs of adidas raquetball shoes from 82, two pairs of cowboy boots, and some loafers from aldo. generally its all complimented with either some large sunglasses, or black framed glasses, a watch(either omega, mont blanc, vacheron constantin, or pateke phillipe) and stuble on the face.