Jessie - Pokémon Yellow
The world of Pokémon is full of illogical and eye-catching hairstyles both on the battling monsters themselves and maybe even more so on their trainers. Despite all the competition, Jessie from Pokémon Yellow still has the hairstyle that stands out the most. Not only is it purple, ridiculously long, and crafted to end with a perfectly precise curl, but it also stands out behind her back on its own with no support. The gravity-defying look went from a funny detail of the game to a full on iconic aspect of the franchise when Jessie became one of the main villains in the classic cartoon series. If her Pokémon can’t get the trick done, at least she can always distract her competition with her bizarre slicked back look.