Prom season is in full swing and that means sparkly floor length gowns, box tuxedos, fancy updos, and inevitably cringe-worthy prom pictures. Thankfully, even our favorite stars aren’t immune to the awkwardness that goes with prom. From Jessica Alba’s Heidi-inspired prom dress to Adam Levine’s all-white tux, these 20 celebrity prom looks are bound to make your sides hurt.
Michelle Obama
Before she graced the cover of Vogue, our First Lady clearly went through some fashion—and furniture—don’ts. But check out that low-cut, high-slit dress! You go girl!
Will Ferrell
Someone had a great sense of humor, even back in high school. Lookin’ good in that tiara, Will.
Ellen DeGeneres
Have you ever seen so much plaid? Even in 1976, this seems like too much.
Wiz Khalifa
Why so serious Wiz?
Usher
Holy corsage! Usher really went all out. Perhaps he was making up for the fact that he did not coordinate with his date. At all.
Bruno Mars
The “Uptown Funk” singer has always had an infectious smile, but we are really questioning that plant around his neck. Like, why?
Adam Levine
Talk about looking washed out—the pair practically blends into their outfits! And we’ve got to talk about those coattails. Even for the ’90s, what was Levine thinking?
Jessica Alba
As dreadful as her dress may seem today, she was clearly very proud of it at the time.
Lizzy Caplan
It’s easy to see why Caplan was cast to play Janis Ian in Mean Girls.
Blake Lively
Would you look at those bangs? And that tiny tiara? Other than that, it doesn’t look like she’s aged a day. Not cool, Blake.
Paul Rudd
One word: Mullet.
Brad Pitt
All white everything should really be reserved for your wedding.
Ashton Kutcher
Kutcher has clearly always been the life of the party.
Ryan Seacrest
That awkward hand placement is EVERYTHING.
Snoop Dogg
Judging by the look on his face, prom just wasn’t his thing.
Tyra Banks
Damn! Tyra knew how to strike a pose, even back in high school, but the awkwardly placed plant is what really makes this picture.
Lady Gaga
After seeing her in a meat suit, Gaga—Stefani, back then—looks surprisingly tame in this thin-strapped blue dress.
Nicole Polizzi (Snooki)
Her date was really showing off his best tough guy ‘tude. It didn’t work.
Jimmy Fallon
“My date went tanning that night,” Fallon tweeted when he posted this picture to his Twitter. Either that or he was just trying to make up for the fact that he looked like a ghost.
RuPaul
We had to save the best for last. Even before he became one of the greatest drag queens in the world, RuPaul was already hard at work in high school.
