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    26 Outfits From Teen Movies, Ranked From "Oof" To "This Is Worth A Billion Dollars"

    You should know what #1 is.

    26. Heather's crop top outfit from John Tucker Must Die.

    wearing low rise pants and a very small crop top
    20thcentfox / ©20thCentFox/Courtesy Everett Collection

    I understand the '00s were a tumultuous time for ensemble choices, but this crosses a line.

    Not only is there a teeny tiny shirt ‚Äď with white low rise pants, dear lord ‚Äď there is another teeny tiny shirt underneath. The fake undershirt thing and the button situation are so weird and bad. Also, her scarf-belt doesn't go though the belt loops, and that is really bothering me.

    wearing low rise pants and a very small crop top
    20thcentfox / ©20thCentFox/Courtesy Everett Collection

    Best Element: The purse and how it matches the outfit.

    Worst Element: The shirt.

    25. The dress Viola from She's the Man changes into and out of a million times.

    Viola wearing a midi dress with small straps
    Dreamworks Pictures

    It feels amazing to me because of the stellar scene Viola wears it in, but when I look at the dress on it's own, yeah, it's a nah.

    Small straps don't do it for me in general, and there's no part of the dress good enough to make up for them. Like, the outfit is just kind of there. I'd probably keep it if someone gave it to me as a gift, but I wouldn't try it on in a store, you know what I mean?

    Viola wearing a midi dress with small straps
    Dreamworks Pictures

    Best Element: The color.

    Worst Element: The tiny straps.

    24. Emmett's baseball outfit from Twilight.

    Emmett wearing a velour tracksuit and a backwards baseball hat
    Summit Entertainment

    It forces me to genuinely ask: What is going on?

    I could stare at this for hours. Is the angle of the plaid cap sending me a message? Is the zipper's placement a hint? Is the black bracelet a cry for help? What about the blue bracelet I just noticed for the first time? What does the lack of shirt imply, and is it horrible? This outfit is a portal into a world of uncertainty, and I tip my sideways plaid cap to that.

    Emmett wearing a velour tracksuit and a backwards baseball hat
    Summit Entertainment

    Best Element: The confidence it exudes.

    Worst Element: The sideways plaid cap.

    23. Sam's dress at the Halloween party in A Cinderella Story.

    Sam wearing a strapless ballgown
    Warner Bros / ©Warner Bros/Courtesy Everett Collection

    We must give thanks to the outfit that inspired a perfect line: "Love her dress. Hate her." 

    Alright, there are layers to this one, so strap in. Obviously I love this dress because it's perfect...except for the sparkly middle bit, which I think is 100% ugly. I never registered it while watching A Cinderella Story, likely because I was transfixed by the magic, but once you see how freaking big the sparkly bit is, it comes close to ruining the whole dress.

    Sam wearing a strapless ballgown
    Warner Bros.

    Best Element: The skirt.

    Worst Element: The sparkly middle bit.

    22. Mia's school uniform from The Princess Diaries.

    Mia wearing oxford like shoes, knee high socks, a skirt, a shirt, and a blazer
    Walt Disney Pictures

    This isn't related to the outfit, but I just had the thought that if they ever made a gender-swaped Princess Diaries, Timothée Chalamet would play the prince, and he would fucking nail it.

    Mia's uniform is not disgusting by any means, but the shoes are clunky blehs and the blazer is too big for it. (I know Mia doesn't always wear the blazer, but I'm considering the entire look, which includes it.) Also, I love a plaid skirt, but pleats have never been a path I chose to walk down.

    Mia wearing oxford like shoes, knee high socks, a skirt, a shirt, and a blazer
    Walt Disney Co. / ©Walt Disney Co./Courtesy Everett Collection

    Best Element: The bow on the shirt.

    Worst Element: The shoes.

    21. Viola's green dress at the end of She's the Man

    Viola wearing a mermaid-y dress
    Dreamworks Pictures

    This dress will be on my mind at least a little bit until I die. Don't ask me why because I don't have an answer more complex than it's green and happy.

    I'm of two minds. Mind One believes the dress is sort of badly 75% mermaid, and the top isn't beautiful. Mind Two believes the dress isn't even my usual style, but look how pretty!!! Mind Two is still six-years old, and she makes a solid argument. A #21 ranking was the compromise.

    Viola wearing a mermaid-y dress
    Dreamworks Pictures

    Best Element: The color.

    Worst Element: The sort of badly 75% mermaid silhouette.

    20. Paulie Bleeker's sweatshirt outfit from Juno.

    Paulie wearing running shorts, a sweatshirt, and a headband
    Fox Searchlight / ©Fox Searchlight/Courtesy Everett Collection

    Of all the outfits on this list, this is the one I'm most likely to wear, and that says more about me than I'd like.

    If there were any more pizazz present, Paulie would rank higher. It's a classic look, but it doesn't stand out like a winner or even a near-winner does. Though, to be fair, the headband stands out hard. Shoutout to the brilliant costume designer who was like, "Get me a headband STAT."

    Paulie wearing running shorts, a sweatshirt, and a headband
    Fox Searchlight / ©Fox Searchlight/Courtesy Everett Collection

    Best Element: The headband.

    Worst Element: The looseness of the shorts.

    19. Seth's party outfit from Superbad.

    Seth wearing sneakers, pants, a long sleeve shirt, and a t shirt underneath
    Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection

    Not including the detergent containers filled with beer.

    I'd buy this shirt and these pants. I'd wear them together. But I would not wear this shirt untucked, and Seth should not have, because it can easily make legs look too short for their body. The short legs throw off the whole ensemble. (But the outfit succeeds in its characterization/story purpose, which is making Seth look like a kid trying to be cool.)

    Seth wearing sneakers, pants, a long sleeve shirt, and a t shirt underneath
    Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection

    Best Element: The pants.

    Worst Element: The length of the shirt.

    18. Regina George's "a little bit dramatic" outfit from Mean Girls.

    Regina wearing flip flops, a mini skirt, a the little bit dramatic t shirt, and a sweater
    / ©Paramount/Courtesy Everett Collection

    Susan from Planned Parenthood called and she wants this outfit.

    I don't like it much, I'll be honest with you. The skirt is solid enough, but, outside of context, I'm not into the rest of the outfit. However, the Mean Girls context makes the outfit legendary. Unlike Seth's famous look from Superbad, here the context outweighs the bad-ness. It's so on-brand for Regina. We know everything we need to know from this outfit alone.

    Regina wearing flip flops, a mini skirt, a the little bit dramatic t shirt, and a sweater
    Paramount / ©Paramount/Courtesy Everett Collection

    Best Element: The "a little bit dramatic" tank top.

    Worst Element: The flip flops.

    17. The two-piece Bianca wears to prom in 10 Things I Hate About You.

    Bianca wearing a crop top and a poofy skirt
    Touchstone Pictures

    10 Things I Hate About You? More like 10 Things I Love About This Outfit, am I right?

    Once I push past the voice in my head who, for some reason, keeps saying this isn't cute, it's cute! Pink is the bomb, and a two-piece, with a big skirt? I'm in. I wish the top were tighter and a different fabric, and I wish the bag never existed, but I'll take what I can get.

    Bianca wearing a crop top and a poofy skirt
    Touchstone Pictures

    Best Element: The fact that it's a two-piece.

    Worst Element: The Lilliputian bag.

    16. Juno's slinky outfit in Juno.

    Juno wearing jeans, the slinky t shirt, and a sweatshirt
    Fox Searchlight / ©Fox Searchlight/Courtesy Everett Collection

    If the hamburger phone were part of the look, we'd have a #1 contender. I don't even know if I'm kidding.

    I have a personal connection to this shirt that I am not going to explain ‚Äď which is annoying, I know, apologies ‚Äď so that's playing a role in the outfit's placement. Also, the plaid jacket is fully fantastic. I want it on my body right now. But I am strongly negative about the scarf and the pants.

    Juno wearing jeans, the slinky t shirt, and a sweatshirt
    Fox Searchlight / ©Fox Searchlight/Courtesy Everett Collection

    Best Element: The shirt.

    Worst Element: The scarf.

    15. The "Jingle Bell Rock" outfits from Mean Girls.

    Gretchen, Regina, Cady, and Karen wearing miniskirts and tank-tops
    Paramount Pictures

    They jingle bell rock. They jingle bell knock my socks off.

    This is another one that succeeds because of context and context alone. The whole thing is purposefully "sexy baby," "we're minors and hot," which is gross, and the movie knows it. That's why the costumes work flawlessly. This is the Plastics exemplifying their "We're the hottest girls in school" vibe, and I love it for that. They are perfect (and hilarious).

    Gretchen, Regina, Cady, and Karen wearing miniskirts and tank-tops
    Paramount Pictures

    Best Element: The whole deal.

    Worst Element: The low waist band of the skirts.

    14. Marty McFly's "I'm in 1955" outfit from Back to the Future.

    Marty McFly wearing sneakers, jeans, a-t shirt, a button-up, a jean jacket, and a vest
    Universal Pictures

    I'm counting Back to the Future as a teen movie because I really want to cover this ensemble.

    It's so '80s. In addition to the shoes and the jeans, which I don't have it in me to unpack, Marty is wearing four things on the top part of his body. Four. I mean, you've got to have a vest over a jean jacket! I dislike said vest and love it in equal measure. I respect it, I'm thrilled it's here, and it's highly unattractive.

    Marty McFly wearing sneakers, jeans, a button-up, a jean jacket, and a vest
    Universal Pictures

    Best Element: The vest.

    Worst Element: The vest.

    13. The Toros' uniforms from Bring It On.

    The Torors cheerleading outfits
    Wonderworks Films

    They are sexy, they are cute, and they are popular to boot.

    With the cut of the top, I want the skirt to be a bit longer and higher-waisted, but it's not a big deal. The outfits are so fun, which, obviously, they should be, they're cheerleader uniforms, but they really succeed. (I'm only talking about the girls' uniforms. I do not enjoy the boys' uniforms.)

    The Torors cheerleading outfits
    Wonderworks Films

    Best Element: The red.

    Worst Element: The length of the skirt waist.

    12. Bender's outfit from The Breakfast Club.

    Bender wearing boots, pants, a long shirt, and a t shirt over it
    Universal / ©Universal/courtesy Everett / Everett Collection

    Claire's outfit is stellar, but it's less famous, so we're discussing Bender's deal.

    Both with and without the jacket, there's a grunge here that I'm a fan of, though no to the vest. Plaid is the shit, and the boots, while overly angsty, work very well. Bender sucks ‚Äď yes, he has awful family stuff happening, but he still sucks ‚Äď so I'm going to paraphrase A Cinderella Story: Love the outfit, hate him.

    Bender raising his fist at the end of The Breakfast Club
    Universal Pictures

    Best Element: The plaid shirt.

    Worst Element: The jean vest.

    11. Let's take a moment to honor Jenna Rink's famous dress from 13 Going on 30.

    Jenna wearing a mini dress and a butterfly necklace
    Columbia Pictures / ©Columbia Pictures/Courtesy Everett Collection

    I should wear sparkly butterfly necklaces more.

    I have no clue if I'd ever wear this out, but I kind of don't care either way, because as a dress for a thirteen-year-old in a thirty-year-old's body, you could not do any better. And I would feel joyous in this because of that. The dress is so inherently young and optimistic, it would rub off on you.

    Jenna wearing a mini dress and a butterfly necklace
    Revolution Studios

    Best Element: The stripes.

    Worst Element: The jean vest.

    10. Mary (Lola)'s outfit at the end of Confessions of a Teenage Drama Queen.

    Mary slash Lola wearing pants with ruffles on the bottom and a tank top with one big ruffle
    Buena Vista Pictures / ©Buena Vista Pictures/Courtesy Everett Collection

    I'm not including Lola's red party dress, but remember that one? Wow!

    There is so much going on. I am required to adore it for its nerve alone. This outfit proves that what they say is true: that girl was a one time teenage drama queen. A hot, tough everyday wannabee. But she'll have changed her destiny. Now she's a somebody. And guess what? That girl was her.

    Mary slash Lola wearing pants with ruffles on the bottom and a tank top with one big ruffle
    Walt Disney Pictures

    Best Element: The ruffles on the pants.

    Worst Element: The cut of the shirt.

    9. Wei Wei's leotard for her beam routine in Stick It.

    Wei Wei wearing a long sleeve unitard with flames
    Buena Vista Pictures / ©Buena Vista Pictures/Courtesy Everett Collection

    I am 1,000,000,000% sure that the brilliance of Wei Wei's beam routine is affecting my ranking, but I'm fine with that. What a scene! What a movie! How is Jeff Bridges in it? Anyway, back to the outfit. It's cute, with the flames, and green is an unexpected choice.

    Wei Wei wearing a long sleeve unitard with flames
    Buena Vista Pictures / ©Buena Vista Pictures/Courtesy Everett Collection

    Best Element: The flames.

    Worst Element: The specific shade of green.

    8. Dionne's plaid look from Clueless.

    Dionne wearing a matching plaid outfit and a very large hat
    Paramount Pictures

    Cher's looks are rightly celebrated, but I think Dionne's looks should be acknowledged more.

    What a hat!!! Not that the outfit needs the hat, because it's fantastic without it as well. As you've heard, I am into plaid, so that's the biggest win in Dionne's ensemble for me. But the shiny, leathery, rain-jacket-y look of the cuffs and the lapel is awesome. I hadn't registered it before, and wow, very cute.

    Dionne wearing a matching plaid outfit and a very large hat
    Paramount Pictures

    Best Element: The plaid.

    Worst Element: The purse, I guess?

    7. Amy's jacket look in Booksmart.

    Amy wearing sneakers, pants, a jean jacket with patches, a sweater, and a shirt
    Annapurna Pictures

    If I were the kind of person who had mood boards, this would be on them.

    I would love to give off this exact vibe. It is what I want to be. My only complaint about the outfit is that the collar feels out of place, according to my eyes. I don't think a Western theme totally fits in. Although, that being said, I would definitely be able to be convinced otherwise.

    Amy wearing sneakers, pants, a jean jacket with patches, a sweater, and a shirt
    Annapurna Pictures

    Best Element: The jacket.

    Worst Element: The undershirt with the Western collar.

    6. The Clovers' uniforms in Bring It On.

    The Clovers uniforms
    Wonderworks Films

    They're cheermarvelous.

    Even if I had been a cheerleader, I don't think fourteen-to-eighteen-year-old me would have been comfortable wearing something so little, but adult me? Give me it! Give me Amy's jacket from Booksmart, a pair of converse, and this outfit! Those three parts may not go together but I will act like they do!

    The Clovers uniforms
    Wonderworks Films

    Best Element: The green.

    Worst Element: The neckline.

    5. Austin's outfit at the Halloween party in A Cinderella Story.

    Austin wearing a colonial-esque outfit
    Warner Bros.

    The gazebo scene is more romantic than the entirety of The Notebook.

    I like an outfit that knows exactly what it is, and this one is fully I'm-the-prince-of-the-story-and-I-want-to-look-cute-on-Halloween. I respect the lane it's built and chosen to live in. Plus, if I could find this outfit for a reasonable price, I would absolutely buy it. Image wearing this to a nice restaurant. The power.

    Austin wearing a colonial-esque outfit
    Warner Bros.

    Best Element: The vibe.

    Worst Element: The inner jacket/top thing, I guess?

    4. Molly's very put together outfit in Booksmart.

    Amy wearing tights, a mini skirt, a turtleneck, and a blazer
    Annapurna Pictures

    A high school gal in a blazer? Unstoppable! We're going to ignore the shoes because everything else is idyllic. The backpack adds such a layer of badass, somehow, and the yellow turtle neck ‚Äď a fucking big, brave choice ‚Äď is impeccable here! This ensemble alone proves why Molly deserved to speak at graduation.

    Amy wearing tights, a mini skirt, a turtleneck, and a blazer
    Annapurna Pictures

    Best Element: The blazer.

    Worst Element: The shoes.

    3. Olive's first "A" look in Easy A.

    ©Screen Gems/Courtesy Everett Collection

    This outfit is maybe the coolest thing I've ever seen. And I've been to Dollywood.

    It should go without saying that Easy A is a stellar movie, and everything around this scene makes the outfit even better. But you can take away the context, you can know nothing about Easy A, and still see how wonderful this outfit is. The confidence. The jeans with the corset. The A. The pearlsssssss.

    Olive wearing jeans, a corset with an A on it, a pearl necklace, and sunglasses
    Screen Gems / ©Screen Gems/Courtesy Everett Collection

    Best Element: The corset.

    Worst Element: The purse.

    2. Cher's Calvin Klein dress from Clueless.

    Cher wearing a mini dress
    Paramount Pictures

    I would like to wear this to a fancy seaside dinner, please.

    It's the kind of dress you speak French in. The kind of dress you win a game of baccarat in. The kind of dress you order sparkling water in. Zero complaints (about the dress, don't love the necklace). I even like Cher's tiny straps! I think about this dress, lol.

    Cher wearing a mini dress
    Paramount Pictures

    Best Element: The dress.

    Worst Element: The necklace.

    1. And finally, Cher's plaid outfit from Clueless.

    Cher wearing a matching plaid outfit and a small fluffy backpack
    Paramount Pictures

    Look, only a world-class bonehead wouldn't give Cher's yellow plaid winner #1, and I'm a slightly smaller bonehead than that.

    Cher wearing a matching plaid outfit and a small fluffy backpack
    Paramount Pictures

    Best Element: Everything.

    Worst Element: N/A.