Pete Wentz 

Fallout Boy was pretty dope—Kanye even jumped on a remix at one point—but we still can't figure out how Pete ended up with a pair of Yeezy IIs at the same time as many more deserving types (unless they worked out some sort of quid pro quo deal in advance). He's been getting laced in Supra and Commes des Garcons x Converse for years and we aren't actually sure why. Lately he's been more famous for being the ex-Miss Ashlee Simpson than anything else.