18. Shinichi Kudo/Jimmy Kudo
Anime Series: Detective Conan/Case Closed
It's too bad this master detective found himself reverted to the age of a child, but at least he knew how to clean up respectably. That means throwing on a bowtie and blue sportcoat, and some smart-looking round glasses. Sometimes he switched it up with contrast-collar shirts and even hoodies and T-shirts, but the round glasses and cow-licked hair remained style staples.