8. Shaquille O'Neal
Shaquille O'Neal was a bit of a cultural obsession of ours in the '90s, and for good reason. The massive Orlando Magic center was charismatic, hilarious, and, contrary to what the laws of physics dictated, somehow dressed well. Shaq very quickly became a veritable superstar who partied with A-list celebs and became nation's favorite gentle giant who could rock dope threads.
When he was wearing suits, Shaq seems to have preferred peak lapels, and was even dressed on the same level as Cindy Crawford with a rust colored double breasted blazer at the 1993 VMAs. But when the big man was lounging around at LSU or recording Shaq Fu: Da Return, he was more inclined to rock comfy athletic gear, including pieces from his clothing line TWIsM. It's hard for large dudes to usually look this good without looking like ill-dressed giants, but Shaq managed to pull it off, unlike his rapping career.