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.