9. Jason Dill
Hands down Jason Dill has had the most transformations in skateboarding. But you know what, I can’t even hate on this dude. You know why, because yes his look changed a lot, but he never seemed to follow or imitate others. Dill was a pioneer. He wasn’t trying to look like anyone else, quite the opposite, people were trying to look like him.
Remember when he wore the capri shorts with yellow leggings in DVS’ Skate More? Yes you see it a lot now with Japanese skaters and even The Muska, but Dill did this in 2005, way before either were doing this. Yes, it’s true, Dill has worn some weird get-ups. But there is definitely something to be said about an originator, not an imitator. Respect due son!