24. Josie Grossie from Never Been Kissed
I can’t even contemplate the sadness of this outfit.
23. The Barbie Trio from Never Been Kissed
I mean, this isn’t even remotely close to prom attire.
22. Andie McPhee from Dawson’s Creek
Andie’s purple-on-purple-on-purple look isn’t so bad considering this was 2000…but it’s the hair and makeup combo that make this look really unattractive.
21. Britney (as “Lucy”) in Crossroads
Britney’s pink, shiny, floor-length prom gown was just blahhhhhhhh.
19. Lindsay Lohan as “Cady Heron” in Mean Girls
Because if you’re going to go to prom in regular clothes, at least wear your Mathletes jacket. (And actually in Mean Girls it wasn’t a prom, it was the “Spring Fling,” but that’s close enough, right?)
17. Kat from 10 Things I Hate About You
16. Bianca from 10 Things I Hate About You
This gets a mediocre ranking just because I wore this tulle ballerina skirt/top combo to my prom and I fully regret it.
15. Joey from Dawson’s Creek
Joey could have really done way more for her prom look. This all-black thing is classic enough, but meh.
14. Brenda from Beverly Hills, 90210
The hair is kind of crazy but Brenda probably felt pretty sexy in this slinky number.
13. Ariel from Footloose
A classic, feminine ’80s look that wasn’t too insane.
12. Josie (no longer Grossie) in Never Been Kissed
If you’re going to do a themed outfit, might as well make it something smart.
11. Andie Walsh from Pretty in Pink
So, I kind of feel like this is actually the ugliest dress ever, but you’re not allowed to say that because, you know, John Hughes and iconic pop culture moment. So, yay DIY ’80s dress!
9. Regina George from Mean Girls
That dress is actually kind of a safe move, but what’s really astounding me here is how we never noticed how far ahead of the trend curve Regina was. Flower crown?! See you at Coachella, bitch.
7. Janice Ian from Mean Girls
This definitely makes you one of the cool kids. This will be the greatest story ever to tell once you’re in your twenties and beyond.
6. Kelly from Beverly Hills, 90210
Kelly’s flouncy white dress may be dated, but in a kind of ’90s way that you’d probably see Urban selling a reproduction of it.
5. Cordelia from Buffy the Vampire Slayer
Damn, Cordelia. I ordinarily think your outfits are tacky, but your prom dress was pretty red carpet-worthy. And doing your hair in a simple, elegant bun was the way to go.
4. Rose McGowan as “Courtney” in Jawbreaker
Holy crap, this outfit is crazy but also really creative and rad.
2. Jen Lindley from Dawson’s Creek
Leave it to Jen to completely surprise us with a prom outfit that wasn’t at all “fast girl Jen” but was in fact a really feminine and vintage-looking cocktail dress. I’d still wear that.
1. Sandy from Grease
Can’t go wrong with a flirty white ’50s dress, now can we?
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