WHEN: 2011

The Balmain red leather jacket is the statement piece that has our eBay alert on, still, and the Balmain hoodie, Cartier shades, and leather pants are all great pieces on their own. But it's amazing how all these expensive pieces thrown together can look so laid-back. It's probably the occult and heavy metal-inspired brand, Actual Pain's hat that gives it that casual edge. His outfit's so good that we barely even noticed Keri Hilson and Vanessa Hudgens next to him.