Will and Carlton From The Fresh Prince of Bel-Air What to wear for Will: An oversized windbreaker and some slammin' '90s jeans. What to wear for Carlton: Black trousers, white dress shirt, and a classic tennis jumper. How to act: If you're Will, like you're the coolest dude ever. If you're Carlton, like you're pretty much not the coolest dude ever. Image Source: Everett Collection