8. Bill Belichick's Chopped Hoodies

Debuted: 2000
Famed Appearance: On the sidelines for the New England Patriots in Super Bowls XXVI, XXVIII, XXXIX

Bill Belichick's outward appearance resembles that of a telemarketer with sloth-like tendencies. Every Sunday he roams the Patriots sideline with his headset guarded by a drab hood, the sleeves long since abandoned on the sweatshirt like they were the tags. This look may scream, “bum,” but he's got the rings to prove that his style of dress in Lombardi Trophy-chic.