19 Pop Culture Halloween Costumes and Iconic Outfits
19 Iconic Halloween Costumes to Inspire Your Plans — Starting at $5
As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work.
The most iconic Halloween costumes from films, TV, and pop culture have also become increasingly stylish over the years, oftentimes even projecting onto more modern trends. Elle Woods's well-known looks in "Legally Blonde" would now easily pass for the Barbiecore aesthetic; >Cher Horowitz's yellow plaid from "Clueless" has trickled into our everyday wardrobes; and Blair and Serena's schoolgirl uniforms in "Gossip Girl" are pretty much the epitome of academia.
But these outfits also persevere as the greatest because people from all over the world have recreated them Halloween after Halloween. The best part about all 19 of the costumes gathered here is that they are easy to recreate using clothing you probably already own. Sure, you may need to pick up one or two added accessories, such as the proper striped sweater for Bert and Ernie or a red sequined dress for Jessica Rabbit, but for the most part, you won't need to break the bank.
Ahead, find 19 iconic characters you can channel with just as much cultural significance on Halloween night.
Anna Wintour and Grace Coddington
Cher and Dionne From "Clueless"
What to shop: Wolford Stretch Cotton Knee-Highs in White ($40)
Romy and Michele From "Romy and Michele's High School Reunion"
What to shop: Lulus Popular Invite Pink Sequin Mesh Feather Mini Dress ($68)
Frida Kahlo
What to shop: Lily & Rose Flower Headband and Ring: Colorful Frida Headpiece ($39)
Jessica Rabbit
What to shop: ASOS Design Scattered Paillette Sequins Scoop Neck Maxi Dress in Red ($139)
Bert and Ernie
What to shop: Zara Fruit Of The Loom Striped Knot Sweater ($46) and Tommy Hilfiger High-Rise Straight Jean ($149)
Holly Golightly From "Breakfast at Tiffany's"
What to shop: Azazie Casey Black Midi Dress ($119)
Björk
What to shop: Michaels Feather Boa Trim ($5) and Hollywood Fashion Secrets Gentle Double Sided Fashion Tape ($10)
Elle Woods From "Legally Blonde"
Madonna
What to shop: Generation Love Nicole Mesh Lace Bustier ($177, originally $235)
Miley Cyrus
What to shop: Los Angeles Apparel Garment Dye Tank Thong Bodysuit ($36)
"The Princess and the Frog"
What to shop: Cinq à Sept Kael Tiered Midi Dress ($198, originally $495)
Cinderella
What to shop: Rowie Annie Silk Mini Dress ($299)
Lady Gaga
What to shop: Haus Labs Atomic Shake High-Shine Longwear Lip Lacquer Lipstick ($28) and Ray-Ban Meta Zena (Gen 3) AI Glasses ($529)
Marilyn Monroe in "The Seven Year Itch"
What to shop: Tiger Mist Isabelle Dress ($79)
Cruella de Vil From "101 Dalmatians"
What to shop: Quince Faux Fur Long Coat ($134)
Blair and Serena From "Gossip Girl"
What to shop: Betsy Johnson Tartan Rhinestone Shoulder Plaid Bag ($98)
Joel Goodson From "Risky Business"
What to shop: H&M Studio Oversized Cotton Shirt ($90)
"Bride of Chucky"
What to shop: Pilcro Vegan-Leather Asymmetric Snap Moto Jacket ($40, originally $168)
— Additional reporting by Adelaide Giesey
Sarah Wasilak (she/her) is the PS Shopping Director and Social Host. With plenty of experience in the fashion industry and over 12 years as an editor at the brand, she enjoys writing, creating social videos, and interviewing talent across the fashion, beauty, health, and fitness categories. She is the host of the "Dinner for Shoes" podcast and has bylines at InStyle, Elle, Refinery29, Who What Wear, Elite Daily, Byrdie, and The Quality Edit.
Adelaide Giesey (she/her) is a shopping writer at Popsugar. With over seven years of industry experience, she is an expert in all things beauty and enjoys writing across fashion and lifestyle categories. Prior to PS, she helped shape the beauty verticals at Byrdie, Coveteur, and InStyle.
