1. The Notorious B.I.G.
Approximate Weight: 395 lbs.
Beyond the red and black lumberjack with the hat to match, The Notorious B.I.G. was a sartorial force to be reckoned with. Hands down one of the most stylish rappers of all time, he knew what worked for him and also how to upgrade his style without sacrificing his street cred. He looked every bit a viable thug whether throwing dice in a flannel shirt and Timberlands, or decked out in a custom white suit and hat. From the Coogi sweaters, topcoats, and ever-present canes, there's no doubt that his style reigns eternal for portly gentleman everywhere.