Era of Prominence: Late 2006-Mid 2007

Appearing in LRG ads as early as 2004, this period saw Kanye really repping streetwear brands. From the LRG Dead Serious hoodie to gear from Crooks & Castles, A Bathing Ape, OriginalFake, and Billionaire Boys Club, he wouldn't be spotted in half of these brands today. That isn't to say he's abandoned the streetwear world forever, as he's known to mix in the occasional snapback or Supreme piece every now and then.