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It’s hard to choose just one outstanding Britney moment, but the singer’s look in “…Baby One More Time” is at the top of our list. To steal her look, all you need is a cardigan, a button-down shirt, miniskirt, socks, and—if you’re daring enough—an exposed midriff. As a bonus, you probably own all or most of those items already!
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Available in sizes XS to XL.
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Available in sizes 00 to 14.
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Available in sizes 14 to 24.
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Clueless
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Photo:
Paramount Pictures/Getty Images
While Iggy Azalea’s spot-on rendition will be hard to live up to, we still think a Clueless costume is the perfect easy-’90s throwback. Whether you copy Cher or Dionne, or dress up with a friend and channel both, just make sure you have a plaid blazer and plaid skirt on.
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Available in sizes 0 to 14.
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Available in sizes 0 to 14.
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Wednesday Addams
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Photo:
Orion/Paramount
If you think you can get away with not smiling all day, consider channeling the morose Wednesday Addams. All you need is a black dress, a white collar, and sleek braids, a look that also happens to be very Saint Laurent.
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Available in sizes 38 to 40.
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A Spice Girl
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Photo:
Ron Galella, Ltd./WireImage
This costume is particularly ideal if you can find four willing friends to accompany you, but the Spice Girls have such distinct and recognizable personas that no matter who you choose, any ’90s kid will instantly appreciate the idea (though we have to admit, our pick would be an LBD-clad Posh).
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Available in sizes XS to L.
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Romy and Michele
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Photo:
Touchstone/Getty Images
Grab your best friend and channel the dynamic duo of Romy and Michele’s High School Reunion. What you’ll need: blonde locks (or a wig, of course), a sparkly choker necklace, shiny pleather-esque minidresses (DIY anyone?), and heeled mule sandals.
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Available in sizes XXS to XL.
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Available in sizes P to L.
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Available in sizes 23 to 29.
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’90s Winona Ryder
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Photo:
The LIFE Picture Collection/Getty Images
We’re totally into this look for every day, not just Halloween! But if you decide to be ’90s-era Winona Ryder this year, try combining a Ramones tee with high-waisted Levis and a leather belt.
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Available in sizes XS to XL.
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Available in sizes 24 to 34.
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Available in sizes S to L.
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Reserved for daring dressers, the Baywatch costume is sure to stand out. If you’re not comfortable spending the night in a red one-piece, we suggest covering up a little more with denim shorts.
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Available in one size.
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Available in size 23 to 32.
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Clarissa Explains It All
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Photo:
Everett Collection
To re-create Melissa Joan Hart’s look in Clarissa Explains It All, mix and layer every print in your closet, whether it’s polka dots, paisley, stripes, and plaid. Finish off your outfit with a side ponytail and Doc Martens!
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Available in sizes XS to XL.
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Beloved cartoon character Daria conveniently wore the same thing every day, so this costume’s a no-brainer. Shop for round glasses, a green jacket or blazer, a pleated black skirt, and combat boots to make sure you’re instantly recognizable.
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Never Been Kissed
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Photo:
Everett Collection
Who could forget Josie’s cringe-worthy feathery white outfit in Never Been Kissed? While the costume version doesn’t require you walking around with a lunch tray, for maximum impact, we do suggest imitating her hairstyle as closely as possible. It goes without saying that finding a blouse with feathery sleeves and a collar—or just accessorizing with a boa—is non-negotiable!
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Pretty Woman
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Photo:
Everett Collection
While this is one of the most iconic looks from Pretty Woman, if you prefer to have the larger portion of your waist concealed, we’d go with the polka-dot outfit that Julia Roberts’s character wears to the polo match. However, if you’re bold enough to rock a figure-hugging cutout dress, don’t forget to accessorize with thigh-high boots and oversize hoop earrings!
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Pulp Fiction
Pinterest
Photo:
Everett Collection
To channel the memorable Mia Wallace from Pulp Fiction, all you need is a crisp white button-down and flared black trousers. If your hair doesn’t already happen to look like Uma Thurman’s, we definitely suggest a cropped black wig with bangs!
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There’s Something About Mary
Pinterest
Photo:
Everett Collection
The one thing you need to channel Cameron Diaz’s character in There’s Something About Mary? You guessed it: hair gel—and lots of it! To get your hair to stick up, our friends at Byrdie recommend using this product.
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