12. Neo-Prep

Something happened when the indie band du jour changed from The Strokes to Vampire Weekend. The tight leather jackets and white v-necks started disappearing from rock clubs and tailored khakis, boat shoes, and oxford shirts took their place. Blue blazers got slimmer and striped ties and bow ties became more prominent. Scott Sternberg's Band of Outsiders label became sought after, and he even landed a collaboration with boat shoe originator Sperry Top Sider. The Neo-Prep had arrived, and with it he brought with him all of the pastel colors and critter pants of the old money lifestyle, but left behind an air of exclusivity and horrible, baggy fits.