This time of year always gets us thinking: You know one thing that we really don’t miss about high school? Prom. From finding a suitable date to scoring an invite to the best after-party, it was an all-around stressful experience. And don’t even get us started on the misery inherent in searching for the perfect dress — an epic quest which, looking back at photos over a decade later, appears to have been in vain. But we’re not the only ones who have suffered through this classic rite of passage; luckily, some of your favorite film characters have gone through this crazy dog and pony show, too. Click through to check out our ranking of their sartorial choices from best to worst, and let us know if you agree with our picks in the comments.
#1. Romy and Michelle in Romy and Michelle’s High School Reunion
It doesn’t get better than these coordinating odes to Madonna — specifically, her Blonde Ambition period and the Boy Toy years. The choreographed dance routine to Cyndi Lauper’s “Time After Time” is really just icing on the cake.
#2. Lux Lisbon in The Virgin Suicides
Ah, the lovely, if ill-fated, Lisbon sisters. They really charmed us all, didn’t they? And admittedly, the most magnetic of the bunch was Lux. It might have been all downhill for her after prom night thanks to that dangerous combination of Peach Schnapps, pot, and sexy Trip Fontaine, but here, frozen in time, she looks absolutely happy and perfect — not to mention, effortlessly stylish in a simple sheath dress. This could totally be a Marc Jacobs ad, and not just because Kirsten Dunst and Sofia Coppola are involved.
#3. Buffy Summers in Buffy the Vampire Slayer
Buffy’s hair says Grace Kelly, her retro white halter dress nods at Marilyn, and that dead dude on the floor screams kickass vampire slayer. Does it get more bombshell than that?
#4. Josie Geller in Never Been Kissed
Yay for costume prom! While it’s certainly no DNA Double Helix (god bless The Denominators), Josie’s Juliet-inspired prom ensemble is definitely a step up from that metallic pink French maid number that she was planning to wear the first time around. Having her braces off and Michael Vartan as arm candy helps the cause, too.
#5. Deb in Napoleon Dynamite
Dear god! We know that Deb isn’t intentionally being ironic here, but we’ve spotted similar dresses on the sidewalks of a certain neighborhood in Brooklyn and the catwalks of Ms. Betsey Johnson.
#6. Laney Boggs in She’s All That
How can someone who just witnessed a choreographed dance to Fat Boy Slim look so sad? (Maybe it’s because she can’t see without the glasses that got ditched in her makeover.) Regardless of how she’s feeling on the inside, Laney looks great on the outside here in an elegant, form-fitting black dress.
#7. Carrie White in Carrie
Carrie’s homemade slip dress was actually pretty chic — before that bucket of pig’s blood transformed it into a whole lot of look.
#8. Cady Heron in Mean Girls
Does wearing your Mathletes uniform with a varsity jacket even count as getting dressed for prom? Frankly, we’re far more impressed by Janice’s subversive choice of an eggplant-hued tuxedo, and Regina George’s ability to make a neck brace work so well with eveningwear. So totally fetch!
#9. The entire cast of Drive Me Crazy
The ’90s called, and they want their awful prom fashions back. The painful part is, these outfits were actually totally on-trend at the time.
#10. Annie Walsh in Pretty in Pink
Blasphemy! We know, we know. We’re supposed to love Annie’s DIY dress because she bravely cobbled it out of that monstrous thrift store number that her bumbling dad bought and the vintage one that Iona lent her. But really, it’s soooo ugly, even by ’80s standards. We’ve always wished that she’d just worn Iona’s as is. Now that was a great dress.