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13+ Awkward Celebrity Prom Photos That Hurt To Look At

Prom takes place at a point in our lives when we're unsure of ourselves, hormonal, sweaty, and just all-around not looking or feeling our best. So, it's natural that most prom photos are cringe-worthy.

It's only right that we look back and laugh, and thanks to the power of the internet, we can look back and laugh at celebrities too, and hopefully feel a bit better about ourselves.

Jaden Smith.

YouTube | What's Trending

Here's Jaden Smith wearing what looks like a white Batman costume? Not really sure what he was going for here, but it's definitely awkward.

Taylor Lautner.

Twitter | @PostsToAmuse

The tiara, the hair, the pinstriped shirt — where do I even begin? This photo has awkward written all over it.

But seriously, what's going on with Taylor's hair? Was he purposely going for the electrocuted look?

Kobe Bryant and Brandy.

Twitter | @afroliviaa

Who knew that Kobe Bryant and Brandy had a teenage romance. Small world, I guess!

But let's just bring our attention to the girl in the back for a second. I'm sensing a possible love triangle gone-sour, cause she looked angry AF.

Blake Lively.

Twitter | @JonahGreen

I'm really glad that tiaras were a trend at one point so that we can all look back and laugh.

I'm also laughing at the way her date is just hovering his hands over her shoulders. He must have been nervous.


Twitter | @AkanButNoJeezyy

Okay, normally I would object to ever criticizing Beyonce in any way because I basically worship her, but that dress is more than I can bear.

Bruno Mars.

Twitter | @racslife_

I seriously cannot get enough of this photo. I love Bruno Mars even more now because of this.

This photo is so ahead of its time, switching up gender-norms, flipping off society's prom-photo expectations, setting a major example for society.

Michelle Obama.

Twitter | @ILoveMelanin

I am living for this photo.

But I have questions. Like why is she sitting in a wicker chair? Why does her date look like he just saw a Bird Box demon?

Will Ferrell.

Twitter | @Know

At least we know that Will Ferrell has always been funny, since he was obviously wearing the tiara ironically.

At least I hope so.

But I am curious as to why his date is wearing a lei? Was that just to add a different element to the photo, or?

Jessica Alba.

Twitter | @JimBeamMe

Loving the fact that her prom dress looks like it used to be a Halloween maid's costume. So versatile.

So economic.

Also loving the look on her date's face. That is the look of genuine excitement.

Tyra Banks.

Twitter | @Just_Kandyce

Oh, Tyra, you've come so far.

This photo is giving me a very 80's soap opera vibe that I'm definitely digging. It's substantially awkward, in all the right ways.

Karlie Kloss.

Twitter | @peoplestyle

Mainly, I just want to know if the theme of this prom was magic, or if Karlie's date dressed like a magician on his own accord. Either way, I'm cringing.

Ellen Degeneres.

YouTube | TheEllenShow

I wish I could personally thank Ellen for sharing this photo, because it's everything I had hoped it would be, and more.

Taylor Swift.

Twitter | @SUKKAR

T-Swift, why?

Let's break this down. They're both wearing all-white — which, if done tastefully, can look nice. But in this case it only adds to the awkwardness.

Secondly, her date is wearing a hat and it's backwards — very classy.

But finally, the gang-signs. I really wish that wasn't happening.

Matthew McConaughey.

Twitter | @cole_richwine

The permed hair, the puffy, padded shoulders, and the presumably clammy hand holding, are everything.

But, alas, even when Matthew McConaughey is awkward, he's still cute. It's not fair.

Brad Pitt.

Twitter | @tullycorcoran

If Brad Pit likes girls who wear puffy sleeves, then I'm bringing them back into style. Plus, they're hilarious, and I want to laugh when I look back on photos of my younger self.

Wiz Khalifa.

Twitter | @ComplexMusic

This is only awkward because you can tell just by the look in his eyes that his mom forced him to pose for this photo.

Poor, Wiz.

Danielle Fishel and Lance Bass.


I am so glad this happened.

Boy Meets World and NSYNC. It's ever 90's kid's dream. But all things considered, it's definitely awkward.

Jennifer Aniston.

Twitter | @MyOldSchoolCool

I'm pretty well convinced that it's physically impossible for Jennifer Aniston to look bad. Even when she looks bad, she looks good.

It doesn't make any sense.

Then there's the celebs that somehow looked flawless at prom

Looking back at your prom photo and being embarrassed is a rite of passage. But there are a few lucky celebs that were able to skip the awkward ugly teen phase and go straight to being gorgeous.

Ariel Winter.

Twitter | @celebstylemag

Exhibit A: Ariel Winter and her date serving looks together, in front of a fairy-tale like view.

If I looked half this good at my prom, that would suffice.


Twitter | @Kornel73

Even though Fergie would have graduated high school in the early 90's, when fashion, hair, and makeup trends were spiralling out of control, she still looks like a pageant queen.

Kylie Jenner.

YouTube | hayu

If we were as rich as Kylie Jenner, or were at least born into extreme wealth like she was, we would have all looked this amazing at our prom.

Gigi Hadid.

Twitter | @teamgihadid

Just to rub her exquisite beauty in our faces even more, here's a collage of Gigi Hadid at her prom.

Demi Lovato.

YouTube | No1DisneyFan1

Demi has been slaying since day one, apparently.

Wish I could say the same thing about her date, but what is that pose?