"Homer the Great"
Season 6, Episode 12

When you're the leader of Springfield's illuminati-esque Stonecutters, you're gonna be rocking some serious dictator gear. Robes, giant shoulder pads, patches as regalia, and an enormous headpiece are all part of the deal. The power steez goes straight to Homer's head, leading to his downfall, but for a second there he was the best dressed supreme leader in the world.