43. Chris Farley
Approximate Weight: 296 lbs.
Chris Farley's disheveled style channeled John Candy's classic, put-together menswear looks and infused them with a frat-like, party boy sensibility. You'd nary find him suited up, opting for open buttons and printed Hawaiian shirts under suit jackets instead. And if he did wear a tie, you bet it hung low rather than stay knotted up. There was always a dash of unkempt sprezzatura to Farley's kits, and we remember him fondly for that, as well as his hilarious body of work.