I dig Brandon Burleigh's The Outsiders look. I know it's gimmicky, but he pulls it off.
As for Elijah, I know we all give him shit for his outfit changes, but I personally don't think he's going full Dylan, but more of a psuedo greaser/cholo look. And he pulls it off. Also, at least he isn't reverting to his wannabe Duffle look from way back when.
At the end of the day, he can go from AH18 in Dickies, to Santa Monica greaser, to kilt wearer, just so long as his skating style doesn't change.