Top 10 Teen Movies with the Most Outrageous Fashion
#10: “Freaky Friday” (2003)
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When we saw this movie in the early aughts we were all introduced to Anna’s punk/skater girl vibes and absolutely fell in love. Lindsay Lohan’s character has a distinctly edgy style and puts a lot of effort into standing out as an individual (even if she’s not always successful). Remember when she turns her shirt inside out because another girl at school is wearing the same one as her? Her low slung pants, studded belts and red plaids were just about the coolest thing we had ever seen in 2003.
#9: “Hackers” (1995)
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1995’s “Hackers” isn’t your typical teen movie, considering that it focuses less on your standard high school shenanigans and more on well...computer hacking. But the characters are still teenagers, and aren’t immune to trying out some outside the box styles that actually came to define a trend called cyberpunk. There’s a lot of color, a lot of latex, and an overall effect that is alternative and undeniably intimidating. Also can we talk about the hairstyles? Angelina Jolie’s roughly chopped bangs are iconic and Matthew Lillard’s ridiculous locks are pretty awesome.
#8: “Jawbreaker” (1999)
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“Jawbreaker” is a dark and satirical comedy that didn’t get nearly as much attention as some of its contemporaries. The plot revolves around a group of girls who inadvertently kill one of their own, and have to deal with the consequences. But despite the somewhat morbid premise, the clothing is full of the bright and cheery colors that you’d find at a candy store. The girls keep up their preppy, popular looks despite what’s going on around them, and wear clothing that is clearly not appropriate for the classroom.
#7: “She's All That” (1999)
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Rachael Leigh Cook, who plays Laney Boggs in the teen rom com “She's All That”, is obviously adorable, so the costume department had their work cut out for them when they were tasked with making her look like a total dork. The end result is just a little bit over the top, as she shows off how “artsy” she is by wearing oversized and ill-fitting garments along with overalls. Of course, this movie is perhaps best known for its makeover sequence, where we get to see how gorgeous Laney really is with a little wardrobe change.
#6: “New York Minute” (2004)
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If you were obsessed with the Olsen twins as a kid (and who wasn’t) you were probably thrilled when they released a theatrical movie as teens. In “New York Minute” they play seventeen-year-old twins Roxy and Jane who couldn’t be more different. As always, Mary-Kate plays the “cool twin”, Roxy, and wears band t-shirts and newsboy hats throughout the film along with more flowy boho looks. Despite being in high school, Jane dresses like she’s running for president. And who can forget that towel moment?
#5: “Can't Hardly Wait” (1998)
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It’s not a coincidence that so many of the movies on our list were released in the ‘90s. Despite the fact that so many fashions from this decade have made a comeback in recent years, some of them have stayed firmly in the past - and for good reason. The fashion in “Can't Hardly Wait” isn’t quite as in your face as some of the other movies on this list, but the characters all wear outfits that are subtle yet questionable. There are a lot of shiny fabrics, crochet materials, and of course plenty of grunge looks.
#4: “Romeo + Juliet” (1996)
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In Baz Luhrmann’s interpretation of Shakespeare’s iconic love story, the characters may speak as though they’re living in the world of the Bard, but their outfits are rooted in modernity. And the setting is not Northern Italy but Verona Beach, which looks like a stand in for an American oceanside town. But the setting is ambiguous, because the characters don’t exactly dress like real teens in 1996 either. Mercutio’s outfits are especially bombastic. But we’ll never forget the getups that our two protagonists wear to the party where they meet and fall in love at first sight.
#3: “Confessions of a Teenage Drama Queen” (2004)
It may not come as a surprise that more than one Lindsay Lohan movie made it onto our list. In “Confessions of a Teenage Drama Queen”, Lohan plays Lola, a teenager who is forced to move from her stylish life in New York City to the suburbs. She brings her sense of fashion along with her though, and isn’t afraid to be overdressed among her suburban peers. She isn’t referred to as a “drama queen” for nothing, and proves over and over again that she wants to be in the spotlight with her look-at-me outfits.
#2: “The Lizzie McGuire Movie” (2003)
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Where do we even start with this one? In “The Lizzie McGuire Movie”, Lizzie has just graduated from Junior High and is heading out on a class trip to Rome. From the very first scene where we see Lizzie dancing in her bedroom wearing a newsboy hat and plaid pants, you know the fashion in this movie is going to be good. It gets even better when she meets Italian pop star Paolo - who dresses exactly how we imagine Italian pop stars of the early aughts did. The outrageous fashion peaks with their big performance when Lizzie teams up with her doppelgänger. Before we unveil our top pick, here are a few honorable mentions. “Not Another Teen Movie” (2001) For Making a Mockery of Teen Flick Getups “Stuck in the Suburbs” (2004) For Having SO Many Hats “Spice World” (1997) For Fun, Colorful Clothes & Oversized Platform Shoes “Loser” (2000) Because It’s Worth Watching For Jason Biggs’ Hair Alone “High School Musical” (2006) For Mid Aughts Theatrical Madness
#1: “Clueless” (1995)
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There’s a reason why this is considered one of the seminal fashion movies. Cher’s style in “Clueless” is on display from the very beginning as we watch her use her high tech computer system to help her pick out her outfit. The head-to-toe plaid is mind-bending and iconic, spawning copycat styles that have transcended the decades and are still out there today. Did high school students ever dress like this, even in LA? Probably not. But through “Clueless” we got to be part of a teen fantasy where everyone was impeccably dressed to the nines in the latest trends, even just for homeroom.
