Never Been Kissed Fashion Moments

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

Image Source: Everett Collection

Oh, Josie. A white feather-boa top is never a good choice for blending in "undercover."

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These Classic '90s Outfits

Image Source: Everett Collection

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

Image Source: Everett Collection

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

Image Source: Everett Collection

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

Image Source: Everett Collection

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

Image Source: Everett Collection

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

Image Source: Everett Collection

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.

8 / 9

This Soft Pink Dress

Image Source: Everett Collection

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.

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