24. Jake 'The Snake' Roberts
Sometimes designing attire for a particular wrestler is as easy as falling off a log. Jake 'The Snake' Roberts' outfits featured (surprise!) a lot of snake imagery. Credit must go to whoever decided not to go over-the-top - potentially Roberts himself, given his characteristically understated manner. The reigning in of the snake theme on Jake's attire was a masterstroke, transforming his otherwise standard image with subtle flashes of snakeskin here and there. His boots could well be the best looking boots in wrestling history. A more overblown snake theme would have given the ultra-serious Roberts a disastrous comedic edge, something that was thankfully avoided throughout his career.