19. Ryoma Echizen
Anime Series: Prince of Tennis
Seigaku's tennis phenom had a style as strong as his forehand. The track jacket and hat he always wore was pretty cool, as were the Agassi-like colorblocked polo shirts he clowned fools on the court in. Besides that, he's also sported gear like white cafe racers and jean jackets, proving that even out of his uniform, he can still land some aces.