LL Cool J and the Kangol Bucket Hat used to have one of the tightest relationships. Kangol started out as a British headwear company with the likes of Princess Diana repping the brand in Vogue. But when LL Cool J added this hat to the lineup of his already well-known hat collection, Kangol themselves note that sales had never been higher. This relationship soon blossomed into a beautiful polygamous ordeal and rappers like Run DMC, Eminem, and Rick Ross joined ranks. These were the first bucket hats to really make it big.