Popsugar Entertainment Halloween '90s Halloween Costumes From Pop Culture The Best '90s Pop Culture Halloween Costumes, From The Addams Family to Spice Girls September 10, 2025 by Britt Stephens View On One Page Photo 8 of 18 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 8 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. Shop: Wyeysyt Y2k Jacket ($30) Wyeysyt Y2k Jacket $30 from amazon.com Buy Now Previous Next Start Slideshow HalloweenNostalgiaHalloween CostumesPop Culture Halloween CostumesThe '90sShopping