Nike Air Max 1 

Year: 2006 

For the first few years, Kanye West's urban-prep attire was the look. Yeey's love for runners has always been prominent since his first days on TRL and BET — in '06 Kanye's go-to shoe was the classic Nike Air Max. Nothing crazy, not special releases, just consistent changes of colorways to match whatever shirt he rocked. Even on the red carpet, Kanye's casual was better than anything other celeb's stylist could put together.