29 Most Awkward Celebrity Prom Pictures

May 06, 2019

There is something really endearing about watching celebrities do everyday things. Of course, it makes sense that stars do normal things; they’re human beings, after all. They go grocery shopping, attend weddings, take their dogs for walks, and even pick up dog poop. They might be famous, but they’re still people!

We know this, but it’s still fun to see A-listers have just as many awkward moments as everyone else. Most famous people take stunning red carpet photos, but certain celebrity prom pictures prove they’re still human. Indeed, high school was hard for everyone.

While plenty of celebs skipped the traditional high school experience to make their way through Hollywood, other stars did the whole regular school thing. Accordingly, they went to prom. And lucky for us, there are pictures to prove it.

Many different sources shared these celebrity prom photos, and we’re thankful to all of them.

1. Blake Lively

Blake Lively looks exactly how you think she would look like at a high school prom. She’s decked out in a bedazzled pink gown (that was probably quite stylish at the time!), and she even accessorized with a little tiara. Really, the most awkward part of this photo is this pose.

2. Harry Styles

Just look at this photo of Harry Styles in an oversized tux with the classic early 2000s punk-emo haircut. That bang swoop is epic; the pose is unforgettable! All together, his photo is adorably uncomfortable.

3. Taraji P. Henson

It’s hard to believe a style icon like Taraji P. Henson would ever wear this prom gown! Between the hair, the hem of the dress, the gigantic sleeves, and the kitten heels, it’s just too funny.

4. Amy Poehler

It’s unclear who took this prom night photo of Amy Poehler, but the shot is pretty perfect. She looks like she just stepped out of the ’80s!

5. Bethenny Frankel

Is this really Bethenny Frankel, or is it a bridesmaid during a wedding in the 1980s? We love this look regardless.

6. Tom Brady

Did anyone else think that Patriots football star Tom Brady was incapable of an awkward moment, let alone photo? Let this old prom picture prove otherwise.

7. Britney Spears

Okay, honestly, Britney Spears looks more adorable than awkward in this prom photo. Her dress looks like a figure skater’s costume, but she’s working it!

8.  Jimmy Fallon

This picture of Jimmy Fallon on his prom night is absolute gold. Where are his hands?! Why is his hair sticking up the way it is? It’s bad, but it’s so good.

9. Candace Cameron Bure

As dated as this picture looks, it’s incredibly adorable that Candace Cameron Bure and Scott Weinger actually went to a real high school prom together. That’s a match made in heaven.

10. Danielle Fishel and Lance Bass

Speaking of celebs who went to prom together… Danielle Fishel and Lance Bass certainly tried it out. They may not have had such a great time together, but they looked adorable.

11. Gwen Stefani

We love the effort that went into Gwen Stefani’s awkward prom photo, but we still can’t get over this haircut. Somehow, though, she still managed to look amazing! Is anyone surprised?

12. Carrie Underwood

How adorably awkward is Carrie Underwood? We’re very here for her youthful look.

13. Ellen DeGeneres

Ellen DeGeneres just might have the most awkward celebrity picture of all time. Between the hair, the dress, and the pose, this is the stuff high school prom photos are made of, without a doubt.

14. Jessica Alba

Jessica Alba doesn’t really make this photo awkward. It’s more about the roses at the bottom, the unnatural looking pose, and the weird hand positioning.

15. Matthew McConaughey

You almost have to do a double take to realize the guy in this photo is Matthew McConaughey. He actually looks pretty good for a high school prom though!

16. Josh Duhamel

Actually, Josh Duhamel was on a totally different level. The outfit, the colors, and that facial expression are everything.

17. Will Ferrell

Is anyone surprised Will Ferrell managed to look both hilarious and majorly awkward at his high school prom? Nope, didn’t think so.

18. Taylor Swift

Is it just us, or does Taylor Swift seem like the opposite of the high school version of herself she’s always talking about? She doesn’t even look that awkward at prom!

19. John Stamos

You will never be able to forget this epic cringe photo of John Stamos at his prom. Seriously, it will be etched in your brain forever.

20. Fergie

Is it weird to say Fergie looks awesome in this very dated looking dress? She’s working the long white gloves, too.

21. Jennifer Aniston

Looking at this photo, you would never know that Jennifer Aniston would later have the most coveted haircut in the United States. That’s what we call a glow up.

22. Beyoncé

Who is shocked that Beyoncé looked good on her prom night many years ago? Probably no one! Queen Bey can do no wrong.

23. Josh Hutcherson

This photo of Josh Hutcherson (can you spot him?) at prom with his friends is so pure and adorable. It’s also way too relatable!

24. Lady Gaga

Between the deep tan and the little mini dress, it is very hard to believe this is the Lady Gaga we all know and love. This is amazing!

25. John Krasinski

We didn’t think it was possible, but this photo of John Krasinski with his prom date makes us love him even more. It’s just so painfully awkward!

26. Rihanna

Honestly, Rihanna looks like a star in this prom photo. It’s her date who is, uh, more on the awkward side here. Not to mention that pose!

27. Bruno Mars

Does Bruno Mars look the same now as he did in his prom picture, or are we imagining things? This is still perfect, though.

28. Gigi Hadid

Actually, it’s kind of annoying that Gigi Hadid doesn’t look awkward in any way, shape, or form at her prom. But maybe that’s what happens when you’re destined to become a supermodel!

29. Kim Kardashian

Can you imagine Kim Kardashian with this haircut today? Probably not, but it definitely fits her style back then!