Popsugar Entertainment Halloween '90s Pop Culture Costumes for Best Friends The 20 Greatest '90s Pop Culture Costumes for Best Friends October 29, 2017 by Maggie Panos View On One Page Photo 7 of 21 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 7 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. Previous Next Start Slideshow HalloweenNostalgiaHalloween CostumesGroup Halloween CostumesPop Culture Halloween CostumesTVMovies