59. Kanye West for Louis Vuitton "Jasper"
Kanye Louis the King Jr. owned 2009 when it came to the shoe game. Fresh off a collab with Nike you may have heard of, Kanye dropped news that he was teaming up with French powerhouse Louis Vuitton for a series of pop-luxury sneakers. The shoes were brilliantly designed, named after his friends, and only cost around a grand. The Jaspers, named after Yeezy’s childhood homie and current barber/style consultant Ibn Jasper, was the pair that got the most attention mainly due to the colorway using pink accents (and the fact that they were the most expensive of the set). Pink in 2009? You can’t tell him nothing.