20. Allen Iverson wearing suits that could fit three Allen Iversons.
When: 2005 - 2010
Everyone knows the NBA instituted a dress code in 2005 to combat Iverson's flagrant sartorial middle finger to David Stern, and to "improve" the league's image. Take that as you will, but it's pretty clear that AI either didn't know how a suit was supposed to fit or took style inspiration from David Byrne's comically oversized suits.