26.Heather's crop top outfit from John Tucker Must Die.
Not only is there a teeny tiny shirt – with white low rise pants, dear lord – 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.
25.The dress Viola from She's the Man changes into and out of a million times.
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?
24.Emmett's baseball outfit from Twilight.
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.
23.Sam's dress at the Halloween party in A Cinderella Story.
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.
22.Mia's school uniform from The Princess Diaries.
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.
21.Viola's green dress at the end of She's the Man
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.
20.Paulie Bleeker's sweatshirt outfit from Juno.
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."
19.Seth's party outfit from Superbad.
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.)
18.Regina George's "a little bit dramatic" outfit from Mean Girls.
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.
17.The two-piece Bianca wears to prom in 10 Things I Hate About You.
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.
16.Juno's slinky outfit in Juno.
I have a personal connection to this shirt that I am not going to explain – which is annoying, I know, apologies – 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.
15.The "Jingle Bell Rock" outfits from Mean Girls.
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).
14.Marty McFly's "I'm in 1955" outfit from Back to the Future.
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.
13.The Toros' uniforms from Bring It On.
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.)
12.Bender's outfit from The Breakfast Club.
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 – yes, he has awful family stuff happening, but he still sucks – so I'm going to paraphrase A Cinderella Story: Love the outfit, hate him.
11.Let's take a moment to honor Jenna Rink's famous dress from 13 Going on 30.
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.
10.Mary (Lola)'s outfit at the end of Confessions of a Teenage Drama Queen.
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.
9.Wei Wei's leotard for her beam routine in Stick It.
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.
8.Dionne's plaid look from Clueless.
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.
7.Amy's jacket look in Booksmart.
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.
6.The Clovers' uniforms in Bring It On.
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!
5.Austin's outfit at the Halloween party in A Cinderella Story.
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.
4.Molly's very put together outfit in Booksmart.
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 – a fucking big, brave choice – is impeccable here! This ensemble alone proves why Molly deserved to speak at graduation.
3.Olive's first "A" look in Easy A.
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.
2.Cher's Calvin Klein dress from Clueless.
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.
1.And finally, Cher's plaid outfit from Clueless.
Look, only a world-class bonehead wouldn't give Cher's yellow plaid winner #1, and I'm a slightly smaller bonehead than that.
Share This Article
TV and Movies
Get all the best moments in pop culture & entertainment delivered to your inbox.