17. Satoshi/Ash Ketchum
Anime Series: Pokémon
For every kid that wanted to be the very best, like no one ever was-that meant getting a pair of cuffed jeans, a trucker hat, and a vest. Fingerless gloves sealed the deal. Ash's style tended to mirror Justin Bieber's in a way, getting a little cheesy futuristic as the series went on. The first Ash outfit was hands down the best-and most memorable.