Prom of the past was a way more awkward affair than it is now.
Where teens these days have access to Instagram, makeup artists, and a plethora of fashion sites, some of us only had wedding formal wear stores and the MAC fashion counter. So, yeah. Awkward.
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Let’s take a look back at some of our favorite celebrities attending prom, and hope that we don’t cringe too hard.
Taylor Swift
Taylor Swift attended prom via MTV. No, really!
MTV’s Once Upon a Prom made a fan’s dream to take TSwift as his date come true.
Eagle-eyed Taylor fans will notice that his jersey number is “13” in the episode, which is Taylor’s lucky number.
Drake
Cousins are ride or die. For Drake’s cousin, Jalaah Moore, that’s more than true.
Drake hooked his cousin up for her prom in style, paying for a Rolls Royce and matching outfits for she and her date. He was definitely a hit.
Bella Thorne
Bella Thorne was already famous when her prom rolled around, but that didn’t stop her from wanting to do the night right.
She told People, “Being a part of high school and having every normal teen experience is one of the most important things to me.”
Jason Derulo
Jason Derulo didn’t attend his own prom, so he did the next best thing: he crashed one!
Students at Culver City High School were treated to a performance by Derulo, and got to see him help crown the prom king and queen.
Demi Lovato
Demi Lovato keeps her promises.
When she was in kindergarten, she promised her friend, Nolan, that she would go to prom with him.
Fast forward to prom of 2010, and Demi was there as Nolan’s date!
Tupac
Tupac fan Tashaunna Howard wrote a letter to his fan club talking about how much she loved his music. And the end, she threw in a joke: if he read it, would he take her to prom, since her boyfriend dumped her?
He took it seriously. He paid for her dress and picked her up in a limo!
Brandy and Kobe Bryant
Brandy and Kobe Bryant met at the Essence Awards in 1996. He was still a high school basketball player, and she was fresh off of winning a Grammy.
Kobe asked her to prom, anyway, and she accepted! She even kept the corsage.
Jaden Smith and Amandla Stenberg
This photo is so full of style that I’m at a loss for words. Legends only.
Not only did Jaden Smith attend prom, he did so on the arm of Amandla Stenberg. Yaaas.
Lady Gaga
See, this is the kind of awkward I was talking about.
Turquoise dress? Check.
Oversized, dangly earrings? Check.
A fake tan? Check.
Aviator sunglasses? Double check.
Choices were made, and now I feel way better about my own photos. (Still love you, Gaga.)
Amy Poehler
Amy Poehler’s prom picture is straight out of an 80’s rom com.
From her hair to the many, many folds and ruffles in her dress, I’m gonna go ahead and say that this is what art truly is.
Natalie Portman
Luckily for Natalie Portman, being famous didn’t stop her from having a totally normal prom experience.
Less lucky? Her date messed up their hotel reservations, and they slept in the car. Yikes.
Brad Pitt
Okay, let me know: do we think that this suit is closer to blue, or is it grey?
Because guys…I really want it to be blue.
Brad Pitt’s prom photo has all the best throwback touches, including some classic brown carpeting, an abundance of plants, and…that hair.
Blake Lively
Is any prom complete if it doesn’t involve tiaras?
Answer: no, and I will not hear otherwise.
Blake attended her prom in a bejeweled pink and silver gown that just screams early 2000s.
And I kind of love it.
Rihanna
Once Upon a Prom strikes again! This time, Bobby asked Rihanna to his prom — and she said yes!
That dress is so early 2000s, but I can see Rihanna bringing it back just for the nostalgia.
Harry Styles
Harry Styles hit up prom in style.
Kinda!
He went for a full suit, and paired it with a massive pink flower that honestly would look cooler as a pattern on a suit jacket. But that’s just my opinion.
Robin Wright
President of the United States, Warrior of Themyscira, Ethereal Prom Photo Taker: just three titles Robin Wright has held in her lifetime, all of which are fictional.
And one of which was given to her by me. But I’m allowing it, because it’s my article. Ugh, what an angel.
Gigi Hadid
Gigi Hadid knew what she was doing when she planned out her prom experience.
The daughter of a Real Housewife, she avoided cliché prom looks and went for a simple, red dress. There isn’t even a tiara in sight.
Halle Berry
Of course Halle Berry was prom queen. What isn’t she the queen of? (Don’t answer that.)
I genuinely thought this was a wedding picture, before spotting tiaras on both women. This? Is fashion.
Carrie Underwood
Carrie Underwood attended her prom in 2001 looking cute as a button.
The future American Idol winner graduated near the top of her class, and went on to get her degree — in between winning Idol, of course.
Michelle Obama
Okay, how is it fair that Michelle Obama’s dress isn’t cringe-worthy at all.
In fact, it’s stunning. The satin dress, the blazer, and that slit up the side? This dress would be an amazing thing to wear now.
Britney Spears
Britney Spears’ ALYCE Paris dress was fire af.
The top beading part and halter are some classic prom realness, and her matching satin shoes just bring the whole look to another level. I don’t know if I love it, or if I’ve seen way too many prom dresses today.
Jessica Alba
I can’t find a single thing I don’t love about this picture.
The blurry, soft filter of the camera screams prom. The random placement of what I’m guessing are either pearls, or satin flowers is high art. Posing in front of those roses…we’re all lucky to be looking at this picture right now.
Kim Kardashian
Aw, baby Kim!
Her intricately curled up-do is a prom staple, and we all know it. Paired with a simple dress, it seems like Kim kept prom low-key, but fun and happy.
Ashton Kutcher
Absolutely no one is surprised that this is what Ashton Kutcher looked like at prom, right?
He’s the epitome of life of the party. The only thing better than his moves is everyone in the background, who all fully gave up wearing shoes. I respect them.
Last Updated on April 1, 2019 by Brittany Rae
