Favorite brands: G-Shock, Kidrbot, LRG, Evisu, BAPE

Japanese brands like BAPE, Kiks TYO, and Evisu denim began to captivate the minds and bodies of dudes who just wanted to dress as dope as possible—and didn't mind dropping serious amounts of cash to do so. Before the fame, Kid Cudi worked at the BAPE store in NYC, where he met Kanye West after failing to take off an anti-theft device from a jacket he purchased. West's career was taking off at the time, as his second album Late Registration didn't succumb to the sophomore slump. Appearances in LRG ads and a style that favored Louis Vuitton backpacks and pink polos ushered hip-hop style into a preppier, more luxe phase—peppered with plenty of hoodies that zipped all the way up.

1. LRG Dead Serious Hoodie ('Cause Kanye wore it...)
2. Kiks TYO T-shirt
3. Evisu Jeans
4. Incredible Hulk BAPEStas (Bought from Scott Mescudi at the Busy Workshop)