'90s Halloween Costumes: Will and Carlton From "The Fresh Prince of Bel-Air" What to wear for Will: An oversize windbreaker and some slammin' '90s jeans. What to wear for Carlton: Black pants, white dress shirt, and a classic tennis sweater. 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