Kanye West's 100 Best Outfits

24. The Late Show with David Letterman

WHEN: 2008

Kanye was the musical guest on David Letterman's show in November to promote 808s & Heartbreak and he stunted in a Pastelle varsity jacket and Aqua 8s when he arrived on set. As always, he was on the raw denim trend before the masses got with it, and the camo Louis Vuitton duffel just upped the whole outfit to another level.

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