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The 10 Most Fashionable Teenagers In Movies (PHOTOS)

Sarah Michelle Gellar in a scene from the film 'Cruel Intentions', 1999. (Photo by Columbia Pictures/Getty Images)
Archive Photos via Getty Images
Sarah Michelle Gellar in a scene from the film 'Cruel Intentions', 1999. (Photo by Columbia Pictures/Getty Images)

In only a few days, our tears will be unleashed en mass as "The Fault in Our Stars" opens. And with it, a brand new teen hero will be delivered.

So far – according to our multiple viewings of the trailer per day – it looks (beyond) promising. Shailene Woodley completely epitomizes the wise and amazing Hazel, and in terms of wardrobe, she’s already inspired some of us to re-embrace the effortless style she’s seemingly blessed by. (Hoodies, jeans, and t-shirts will always be okay – we promise.) So with that in mind, we’ve assembled the 10 most fashionable and/or influential heroes of our favourite teen movies (and "Spring Breakers").

1) Kat Stratford ("10 Things I Hate About You")

Bianca may have had her Sketchers and a Prada backpack, but Kat brought the most important style trait to the table: her unwillingness to adapt to social and/or gender conventions. If she wanted to dress up for prom, she dressed up for prom. If she wanted to wear an enormous leather coat to a party, she went for it. And if she wanted to wear camouflage despite the protests of Joey “Eat Me” Donner, she abided accordingly. Kat’s style reflected Kat, and Kat alone. Bianca could keep those pearls.

2) Lainey Boggs ("She’s All That")

Now that we’re older and wiser, we can agree that before Lainey Boggs “got popular” (ie. cut her hair and took off her glasses), her style was still on-point. First, she performed onstage wearing a bodysuit, which any of us can do now since bodysuits are available at literally any 20-something-targeted chain store. Second, she rocked everything from overalls to oversize button-ups with the grace of a woman who dressed to suit her personality: creative and unique. Frankly, it was a blessing Taylor ruined her dress with a drink – Lainey looked better as Lainey, anyway.

3) Cher Horowitz ("Clueless")

Behold: the master. Cher may have set the tone for her high school and those in attendance, but kudos are still in order because she made the rules. She and Dionne may have been each other’s reality check, but ultimately, only they could carry off matching plaid without looking disastrous (thanks to confidence, self-belief, and that crazy computer program). As for second place? Amber, always. Never discredit the power of novelty hats.

4) Kathryn Merteuil ("Cruel Intentions")

Yes, this movie is . . . something. But aside from Kathryn and her stepbrother’s dysfunctional dynamic (and her drug habit, and the fact that no single character in this movie is likeable), we must credit her wardrobe: in addition to great one liners about the double standards of sex, Kathryn brought us dark neutrals, Victorian gothic influence, and lady blazers before Liz Lemon delivered them, mainstream-style. She was private school chic before even Blair Waldorf (but please don’t tell Blair we just said that).

5) Candy and Brit ("Spring Breakers")

That’s right, we’re including "Spring Breakers" – a.k.a. one of the most interesting teen films of the last few years. “But!” you protest. “They didn’t even wear much!” Correct – they wore next-to-nothing. But not only did they re-enforce the importance of neon in what they chose to wear, they used a lack of fashion to reclaim their power. Style doesn’t always have to be about how much you have on, you can still take over the world Florida in a bathing suit.

6) Janis ("Mean Girls")

Behold: the "Mean Girls" character who gets the least amount of fashion attention. While Janis was not actually wearing a wig made of anyone’s mom’s chest hair (though that would’ve been amazing), she did nail counter-culture style with a Lindsay Weir-like grace, opting for everything from layered t-shirts, to high top Converse to an oversize military jacket. Ultimately, she epitomized mid-2000s art school chic – and wore a tuxedo to prom (like a freaking hero).

7) Chenille ("Save the Last Dance")

For the record, Julia Stiles’ "Save the Last Dance" character will never make it onto any sort of “you did well, teen!” fashion list because girlfriend almost wore a Gap sweater set to the bar. (And that’s just nuts.) But thank goodness for Chenille a.k.a. Kerry Washington a.k.a. Olivia Pope who swoops in for a fashion intervention since she herself wore hoop earrings, turtlenecks, and faux fur collars better than any of could ever hope to. Chenille was the cool big sister we would’ve been lucky to have (and we can’t believe she was so okay with hanging out with Julia Stiles, whose character’s name we choose to forget).

8) Juno ("Juno")

We'll keep it simple: a striped t-shirt, a hoodie, and a mini-skirt worn over pants. The 2007 dream, or the smartest choice of all if you needed to walk home from anywhere in the winter and planned on wearing a skirt. Juno knew, you guys. She knew – she got it.

9) Anna Coleman ("Freaky Friday")

In an alternate universe, Anna Coleman and Janis are friends like they are in "Mean Girls" – especially since it would make so much sense. But where Janis brought an “art school” (ish) aesthetic to the ’04 teen movie landscape, Anna gave burgeoning “hipsters” (hear us out) their first wardrobe essentials in 2003. While still piggybacking on the Avril Lavigne-esque punk look of the early 2000s, she re-introduced baseball t-shirts, plaid dresses (what’s up, ‘90s resurgence), every bracelet in the world, and combat boots. Now, they were for everybody. And while some of us still dressed like Gretchen Wieners, it was a step in the right direction for anyone with a penchant for distressed denim jackets.

10) Gina ("Empire Records")

We hear so much about Corey, but for the first time, let’s look past the combat boots and kilt. (No offense, Corey – we’ll come back soon.) Gina brought just as much fashion relevance to "Empire Records" as her Harvard-enrolled friend – more, arguably, since she was labeled according to whom she slept with and (according to Deb) how short her skirt was, giving her clothes some social currency. However, Gina dressed like every other person does now, and closer to Corey than most of us think: aside from clogs vs. boots, they both stuck to a similar mid-‘90s aesthetic – despite Gina’s penchant for Music Town smocks which, honestly, could work with leggings.

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