2009 - Nike Air Yeezy
As DJ Clark Kent has said, the Air Yeezy (and its even more-hyped successor) isn't a performance shoe, it's a performer's shoe. But at this stage, that seems like a more and more irrelevant distinction. Sports and entertainment seem to edge ever closer, and someone who performs as much as Kanye can certainly be considered some type of athlete. But it's the shoe that matters here, and the Yeezy, even with the easily recognizable Air Jordan III sole tooling, was something completely new. Even separated from the considerable Kanye cult of personality, this was a design that could (and did) hold its own.