You can’t have a list of most iconic rom-coms without including Never Been Kissed, and you can’t have a list of iconic movie fashion without it, either. The Drew Barrymore-led comedy is full of moments that really bring us back to the wild world of late-’90s style and all that entails: the good, the bad bad, and the glittery. Who could forget Josie’s shiny pink prom dress or her epic white feather-boa ensemble? We certainly never have – and you probably haven’t, either. Ahead, we’ve picked some of our favorite looks from Never Been Kissed that we still remember perfectly after more than 20 years – even if we never got to dress like that in high school!
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These Mismatched Shirt and Skirt Combos
Where even to start with these outfits? The blue crop tee with a pink skirt? The gold glitter pencil skirt for a school day? The tiny accessories? There’s just a lot going on here, and we’ll never forget it.
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This Attention-Grabbing White Feathered Top
Oh, Josie. A white feather-boa top is never a good choice for blending in “undercover.”
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These Classic '90s Outfits
This trio represents pretty much every late-’90s to early-’00s trend we remember seeing in lunchrooms: wavy striped tops, chokers, polo shirts, and cami-and-cardigan combos.
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This Huge Flower Top
The huge single flower on Josie’s top is attention-grabbing, but soft and sweet at the same time – just like Josie herself.
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These Vivid Green Pants
We have to hand it to Jessica Alba: not many people could pull off the bright green jeans look, especially when paired with more shades of green on top (and that spiky hairdo). But she carries it with total confidence!
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This Black Dress and Dangling Necklace
We love how confident Josie is in this straightforward (but never boring) black dress. The spiky, dangling details on her choker just add an extra boost, showing how she’s coming out of her shell at last.
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These Wildly Colorful Outfits
Totally over-the-top and totally memorable are the best ways to describe this trio of outfits. They’ve got big, bold patterns, bright colors, belly-baring cuts, and some seriously wild accessories. You’ll definitely never forget seeing these!
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This Shiny Ruffled Prom Dress
This one goes up there with Pretty in Pink in terms of prom dresses that are more sentimental than stunning, but Josie’s enthusiasm more than makes up for all the shimmer and ruffles.
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This Soft Pink Dress
Josie is at her most stunning when she’s just being herself. – Herself, in this case, is reflected in this timeless, fluttery pale pink dress – perfect for a romantic final scene.
