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 11 of 18 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 11 Princess Diana What to wear: A crewneck sweatshirt, preferably with a fun, vintage graphic; colorful bike shorts; crew socks; and sneakers. Bonus points for sunglasses. How to act: Like you are literally Princess Diana. Shop: New York Fashion Police Harvard University Sweatshirt ($35) New York Fashion Police Harvard University Sweatshirt $35 from amazon.com Buy Now Previous Next Start Slideshow HalloweenNostalgiaHalloween CostumesPop Culture Halloween CostumesThe '90sShopping