Notable partners: Khloe Kardashian

Lamar Odom and Khloe Kardashian say it was "love at first sight." But maybe Kardashian had her eyes closed, or just forced herself to ignore the basketball player's style. Odom often wears too-baggy button down shirts and trashy tees paired with jeans. In theory, shirts and T-shirts over jeans should work, but more often than not Odom's style is a pile of fails due to poor execution and poor choices, marking him as the least stylish Kardashian boo.