"...Baby One More Time" Britney Spears
🎶 Hit me baby one more time 🎶 Sure, Britney was THE Y2K It Girl, but she dropped one of her most iconic music videos dressed as a school girl right before the turn on the century. So grab that pleated skirt, tie up that white button down, and don't forget the pink scrunchies for your pigtails.
2Shania Twain
Shania Twain blessed us with "Man! I Feel Like a Woman" in 1997, and you too can bless the Halloween party with an iconic look from the country music star's video. Hope you like leopard print!
3The Fresh Prince of Bel Air
Time to sit on your throne as the Prince of Bel Air while you pay homage to the classic '90s sitcom. When you're recreating Will Smith's look, don't be afraid to mix neon patterns and colors.
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4Toni Braxton
If Beyoncé dresses as you for Halloween, you know you're an absolute icon. Toni Braxton was IT in the '90s, and if you aren't signing "Un-Break My Heart" all night long, you aren't doing the costume justice.
5Storm from X-Men
Yes, Storm has been around well before the 1990s, but she plays a huge part in the '90s cartoon, X-Men: The Animated Series. Just make sure to rock some silver hair, icy contacts, and practice harnessing the power of the weather.
6Jessie from Toy Story
A little bit of yee and a lot bit of haw. Everyone's favorite cowgirl from Toy Story can be replicated with her famous red hat, pigtails, and of course, we can't forget her cow-print pants.
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7Mia Wallace from Pulp Fiction
It's amazing how recognizable Mia Wallace's bob and button up shirt combo has become. All you need are some dance moves and a cigarette (for aesthetic purposes, ofc).
8Catwoman
All hail Michelle Pfeiffer's version of Catwoman. Her stitched up catsuit reigns supreme in our book when it comes to who portrayed the famous character best. For this look, you'll need an all black ensemble and of course, her detailed face mask.
9Pamela Anderson from Barb Wire
We've got an unlimited amount of fire emojis for this costume. You can recreate Pamela Anderson's character from the 1996 movie by rocking blonde tresses, a black corset, some fishnets, and a bold smokey eye.
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10The Matrix
The Matrix had everyone questioning reality when it was released in 1999, and even years later, the film's all-black outfits are as timeless as ever.
11Romy and Michele's High School Reunion
BFF duo Romy and Michele were the stylish characters we all wanted to be back in the '90s. Dress as a reimagined version of the dynamic duo by wearing colorful monochromatic outfits. Add on some choker necklaces, platform heels, and Post-it sticky notes to complete your look.
SHOP RHINESTONE CHOKER NECKLACE
12Ed and Dexter from Good Burger
Welcome to Good Burger, home of the Good Burger. Grab a bestie, striped shirt, and paper hats to recreate this iconic fast-food duo.
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13Gwen Stefani from No Doubt
Rock out this Halloween with a look inspired by the singer's style in her band's music video for "Spiderwebs." Pair a cropped tank with low-rise plaid pants, and combat boots to complete the look.
14Men In Black
You want easy? Then this costume is for you. All you should have on hand is a black suit (a black blazer and trousers will totally do), a white button-up shirt, and black sunglasses to channel that whole "I investigate mysterious alien encounters" energy.
15Carmen Sandiego
Take a cue from Pedro Pascal at the 2023 Met Gala and pull out allllll your red for this look. Of course, you'll need a red trench coat and a wide-brim red hat to go full Carmen, but for your base, you can just wear some plain black basics (think a long-sleeve shirt and leggings).
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16Titanic
First of all, there was 10000% enough room on the door for both Rose and Jack!!! But I digress. Bust out your finest beaded dress and opera length gloves to transform into the lovestruck Rose.
SHOP HEART OF THE OCEAN NECKLACE
17Missy Elliott
The hip hop icon gave us some memorable songs and looks, including the black balloon-like outfit she wore for several performances in the '90s. Recreate a costume inspired by this number with a couple extra large trash bags, white sneakers, and silver hoop earrings.
18Meredith Blake from The Parent Trap
Name a more stylishly iconic villain, I'll wait! While she threatened to ship her would-be step-daughters to boarding school and was generally not the nicest person, her wardrobe was *chef's kiss*. Case in point: The look she was wearing when she's first introduced in the movie, which only requires a ~fancy~ black hat, white sheath dress, some dainty gold jewelry, and color-coordinating your red mani with your lipstick.
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19Selena
Selena Quintanilla-Pérez, known by beloved fans simply as Selena, was a musical and fashionable force. She had glamorous performance style and could rock just about anything and turn it into a fly 'fit. For this classic Selena ensemble, reach for her legendary purple jumpsuit ensemble.
20Ms. Frizzle from The Magic School Buss
Didn't we all want Ms. Frizzle as our teacher growing up?! Not only was she smart and wise AF, she also had truly impeccable style. Just find a blue shirt dress and stick on a bunch of planetary-inspired appliqués to channel her quirky vibe.
Mekita Rivas is an editor at Cosmopolitan, where she primarily covers fashion, culture, and lifestyle. She writes about everything from the best leather totes and books she can't put down to plants, podcasts, and politics. Prior to joining Cosmopolitan, she was a senior contributing fashion editor at PopSugar and Bustle. Her writing has been published in dozens of publications including The New York Times, Vogue, Harper's BAZAAR, Women's Health, Refinery29, and others. She currently splits her time between New York City and Washington, D.C. Follow Mekita on Instagram, where you'll typically find a mix of her snapshots from fashion week and various editor travels.
I'm Cosmopolitan's Associate Fashion Editor and write about any and all trends, major celeb fashion moments, and why wide-leg jeans are basically the best. I originally moved to New York City to audition for RENT, only to find out that the play closed 10 years ago.
Chaise Sanders is an Associate Editor at Cosmopolitan, where she covers anything from lifestyle and beauty to entertainment and style. Wanna upgrade your skincare game? She's got you covered with the best facial cleansing brushes. Or maybe you're in need of a new true crime show to binge? Got that covered too! Prior to joining the Cosmo team, Chaise was an editor at Country Living (also part of the Hearst fam) where she interviewed celebs like Dolly Parton, LeAnn Rimes and even Martha Stewart. Now, as one of the Big Apple's newest residents, there's a good chance that you can catch her checking out an Insta-worthy cafe or spending way to much $$$ in vintage stores.
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