After wearing dreads for nearly five years, John says his new look feels much lighter. "The clothes are great. My mom is as happy as she'll ever be, so it's awesome," he says. "It's very reminiscent of a long time ago."
Jacket: Calvin Klein, Dillards.com; jeans: Levi's 510 Super Skinny, Dillards.com; shirt: Tasso Elba, Macys.com; shoes: Johnston & Murphy Melton, Dillards.com; tie: J.Crew.com.
Tim Gunn makes over Santa Claus, Shaft and a modern-day caveman