About this blast from the past, Jimmy Fallon said, “my date didn’t tell me she was getting tan and high heels for the prom. Standing next to her, I looked so pale and so small.”
It’s always a good idea to coordinate with your prom date, but this planning mishap surely made for an unforgettable photo! Poor Jimmy, though he’s grown into himself quite a bit since then…
Before she was one of the top pop stars of all time, Britney Spears was just like any other average girl who, at one point, had to dress for the prom. And here, she looked super glamorous with her jeweled, coral halter dress.
Britney sported brunette locks before her signature blond hair, but in many ways, she still looks like the young beauty that she is here.
Here, Jenn doesn’t look anything like the Hollywood megastar that she is today. But she still looked ready to have a great time at prom with her brown updo, timeless black dress, and simple, elegant jewelry.
And her date (who quite frankly has strong Ross Geller vibes) kept it traditional with a tux and bow tie. We can’t help but wonder where Jennifer’s prom date is today and if he ever thought that his prom date would eventually become one of Hollywood’s biggest sweethearts.
The stunning actress was already famous at the time of this photo. Natalie Portman began her film career at the ripe old age of 12, and though fame infiltrated her early life, Natalie was still able to enjoy the simpler things like going to prom.
She chose a sparkly, strapless blue dress, and the look was sealed with a sheer shawl and glittery silver bag. Natalie looked happy to just be a normal girl for a night!
Before she was an “SNL” cast member and comedic actress Amy Poehler was just a teenager on her way to prom. The look? 80s chic complete with curly bangs, pearls, and a ruffled strapless dress. The lovely bouquet really pulls together the entire look.
Though this way before she was a household name, it’s undeniable that this really is Amy Poehler. We bet she was as funny in high school as she is today!
Sure, she and her husband Ryan Reynolds often look like deities on screen. But, like everyone else, she’s had her awkward moments too. And this photo proves that Blake Lively, who’s often on everyone’s list of best-dressed, is a human being and was once as awkward as you.
The pink sequins of her dress and that tiara tell us this happened in the early 2000s. Also, those side bangs!! In any case, the smile on Blake’s face tells us she had a blast at her prom. And, ultimately, that’s all that matters!
Before she was a member of Destiny’s Child and later a solo artist, Beyoncé was simply the daughter of a small-town preacher from Texas. She went to the event with her longtime boyfriend (who apparently, later made a horrible mistake and cheated on her).
But Beyoncé, who clearly would even look beautiful in a potato sack, looked like she was enjoying this night. Little did she know the bright future ahead of her, and we’re pretty sure her date is counting his losses now.
Long before “A Star is Born,” Lady Gaga was your average New Yorker. But, can you spot Lady Gaga in this photo? We’ll give you a hint; she favored the “bronzed” look.
Though she is super tan, Lady Gaga still looks striking in her aqua blue dress, simple updo, and pretty corsage. Compared to what she wears today, this is a rather understated look.
At first glance, this looks like Reese Witherspoon’s look-alike daughter, Ava. But if you study the photo closely, you can see a very young Reese. It’s a bit of a challenge to see from the black and white photo exactly what her prom look was, but it looks like she chose to keep her dress, hair, and jewelry simple and beautiful.
What is incredibly clear from the photo is that Reese has barely aged, and her elegant class has stayed the same through the years.
Here we have one of the most legendary acting icons in Hollywood today – Meryl Streep. Fans know that Meryl doesn’t do any of her performances halfway and, years ago, she even went all out for prom!
While managing to let her natural beauty shine through, she chose a graceful dress that included arm-length gloves. Meryl is certainly sporting a ’60s debutante look here, but it looks lovely on her — and so does her date.
Brad Pitt chose an unconventional grey suit and tie for his prom. And underneath his almost mullet hairstyle, you can still see the makings of “People” magazine’s Sexiest Man Alive.
As for his date, she chose a white dress that, at first glance, makes this look like a wedding photo shoot. Today she must be star-struck looking back at this photo.
Robin Wright is pure elegance in her prom photo and, with her delicate tiara, you might even say she looks like a princess (pardon our overt nod to her iconic role in “The Princess Bride”).
With her flowing hair, strapless dress, and a single strand of pearls, the overall look is timeless. And Robin still looks as beautiful today.
Will Ferrell was pulling classic Will Ferrell moves by stealing his date’s tiara for himself. Other than that, Will kept to the typical attire — except that he was missing his suit jacket and stuck with the shirt and bowtie for this picture.
His date chose to accessorize with some unique necklaces to compliment her black dress, but her best accessory that night was her beaming smile. After all, having Will Ferrell as your prom date hardly makes for a lackluster night.
Coral is a great color on Demi Lovato, and it looked even better in this strapless dress. There is a touching backstory to this photo of her and her date. Apparently, Demi went to her friend Nolan’s prom to fulfill a childhood promise she had made.
And here in 2010, Demi had already secured celebrity status, which may have caused a stir at the event. But she still looked like she was having a blast just attending a friend’s high school prom.
Fergie was sporting a very glamorous vibe in her sparkly, black prom dress. The spaghetti straps cemented the 90s look, but what really set her apart were the over-the-elbow black gloves.
Now a household name, Fergie has definitely retained her glamorous style through the years.
While you may expect Jessica Alba to wear a glamorous, sequined dress to her prom, she chose a very different dress. The bodice looks to be velvet with little white flowers around it.
And with the delicate headpiece, this look is a very fairytale princess (or alpine milkmaid). But milkmaid or not, Jessica looks happy with the date she chose and excited for her prom.
George Clooney and his date looked like they were excited for prom night. The 70s strike again with another prom photo that could be mistaken for a wedding photo.
One of the things you notice first is his date’s white dress; the second is George’s hair! And if you look closer, you’ll see that George is wearing a classic, ruffled 70s shirt.
Here’s Gigi Hadid’s prom look in 2013 is definitely more understated than what we’re used to seeing her in, even on a casual weekday!
Being a supermodel, you may be used to seeing her in high fashion on magazine covers and the runway. But even in her bright coral dress, she looks stunning.
You’re often used to seeing Jon Hamm in suits from his role as Don Draper on Mad Men, but here you see a more approachable Jon. Jon is all decked out in a tux, and we can forgive his messy hair for the bashful smile.
His date had a red carpet style with her black, scoop neck dress and white choker. Both he and his date looked very glamorous and, honestly, a little bit “Mad Men” inspired.
Alright, alright, alright! Matthew McConaughey has the same beaming smile today as he had in his prom photo. The couple did a great job of coordinating their colors (and overall 80s vibe) for the event, with Matthew’s blue bow tie and his date’s royal blue dress.
Judging by their seemingly authentic smiles and hand-holding, they may have been more than just prom dates.
The absolute first thing you’ll notice about Taylor Swift’s prom photo is the lack of a traditional prom pose. While it’s mind-boggling why her date chose a white ball cap for his ensemble, the two at least matched in all white.
Taylor was also sporting kitten heels, which, being 5’ 10”, might have been, so she didn’t make her date feel too short. Though she was already a star here, it looked like she wasn’t having a boring time just being a regular teen.
Judging by the expression on Josh Duhamel’s face, this may have been a candid photo. He went all out for his prom suit to include a cummerbund, although the fanciness ended with his hair.
But considering everything below his hair seems to be on point, perhaps we can give Josh a pass.
The former member of One Direction and now solo artist kept his prom look simple yet put together. Harry’s signature wild mane added interest to his otherwise traditional look.
His date also looked very polished with her one-shoulder dress and graceful updo. Little did this girl know there would soon be so many others wishing they could be in her shoes.
There is a lot of hair happening in this prom photo! It’s hard to find John Stamos under all that hair, but he’s there.
All of the ruffles shared between the two indicate the 70s, along with Stamo’s white suit and his date’s Farrah Fawcett-inspired hair. Maybe after prom, they headed to the disco.
Long before she graced the stage, dancing, giving interviews to famous people, and making us laugh till we cry, Ellen Degeneres was just a regular girl. Between her and her date, the two are really competing with each other with their outfit colors.
Ellen selected a floor-length, plaid dress for her prom, while her date chose a deep red suit, a light pink shirt, and what looks to be grey pants. These appear to be bold (and even outrageous) choices now, but at the time, they were on-trend!
What can be said about Jaden Smith’s prom ensemble? He made a truly unique choice when he decided to go to prom in a white Batman suit (yes, Batman). He at least did add a light-colored suit and champagne tie for some tradition.
His date looked beautiful in a white, cut-out lace dress and, based on her smile, had a wonderful time with her caped crusader.
Ariel Winter chose a gorgeous blue lace dress for prom. The floor-length dress also featured an open back, which was completed by a generously sized corsage. We love that Ariel let her lustrous dark hair down and is also pictured here with friends.
All three of them look like they are not only headed to prom together but celebrating their friendship. What is most beautiful about this photo is Ariel’s confidence.
Kim wasn’t a household name when this picture was taken for her prom memories. She went to prom with TJ Jackson, the nephew of Michael Jackson, and the two looked like they were happy about their choice of date.
Kim decided to keep the early 2000s trend of a curly updo while TJ looked uber polished in his tux.
Another former member of One Direction, Liam Payne, sported his iconic hairstyle for prom night. The group didn’t look ready to pose for the photo, but at least Liam and his date were coordinated with her purple dress and his purple tie.
No doubt this was one last everyday memory before Liam and his future One Direction bandmates left normal life behind.
Elle Fanning was already a star at the time of this photo, so she knew how to create a jaw-dropping look. Her dress looked like it was made for the red carpet and not for the halls of a high school, and that’s because it was.
Elle couldn’t actually go to prom because she had to attend the Cannes Film Festival. Her prom date then flew out to see her and do a photoshoot with her. It’s remarkable that Elle still wanted the experience of prom when she had a red carpet event to attend. What a memory!
Carrie Underwood flashed an authentic smile in this sweet prom photo. Before she unleashed her powerhouse voice to the world, she kept her small-town girl charm with her headband and the subtle waves in her hair.
Even here, so many years ago, Carrie looked like America’s sweetheart. And her date also looked very dapper in his white suit with black-tipped lapels.
Would you expect anything less from Ashton Kutcher’s prom photo than him being in the center of the dance floor?
It’s unclear if he had a date or not from this photo, but it is clear that he came to have a great time. It looks like he donned the traditional tux but ditched the jacket to get down to dancing.
Youtuber Tana Mongeau was already pretty well-known by the time she headed to prom. Today the internet celebrity has millions of subscribers to her YouTube channel.
The beauty kept her blond hair down and let her bi-color black and gold dress steal the show. Her date also looked great in his grey suit that was accented by a metallic bow tie.
Lance Bass took “Boy Meets World” star Danielle Fishel to his prom. Today Lance is married to Michael Turchin, but long before he came out, he dated Danielle. And a young celeb relationship like this one would have been a delight to fans!
Here Lance had the customary bleached hair for the time to go with his prom suit, while Danielle wore a gorgeous white dress with chunky silver heels.
Nicole “Snooki” Polizzi
The first thing we notice about Snooki’s prom photo is that she wanted to be tan…really tan. Aside from her startling skin tone, she looked beautiful in her Cinderella blue dress and tiara.
Her date decided to keep a more stoic expression but still looked striking with his long black suit.
Porsha Williams kept her look all black and classy with an elegant, high neck dress. “The Real Housewives of Atlanta” star shared this photo with fans that were taken in 1998. But who is Porsha’s well-dressed mystery date?
Whoever he was, he was apparently cute! “Wow, my cousin sent me this offline! Prom 1998 […] Who scratched my date’s face…he was cute,” she remarked.
Though he lacks star quarterback confidence in this photo, Tom Brady still looked like he knew how to properly dress for prom. We don’t know where his suit jacket went, but he at least had the shirt, vest, pants, and bow tie-down.
We hope he had a great date lined up for the prom but, if not, young Tom wouldn’t have to worry as he would later be an NFL quarterback married to Victoria’s Secret model Giselle Bundchen.
John Krasinski has come a very long way from the nerdy guy on “The Office” to the leading man he is today. There is such a variety of looks for the couples in this picture, but John chose a classic suit and a patterned tie for himself.
His date also looked lovely in her captivating pink dress. And underneath the endearing awkwardness of this photo, you can still see that adorable John Krasinski smile.
Taraji P. Henson
There is nothing understated about Taraji’s prom dress! The future actress selected a dramatic, pink, winged-sleeve dress that sort of wore her honestly.
But, despite the overwhelming dress, Taraji still looks lovely with her angled updo and corsage. Thankfully, as a star, she has honed her style today.
Famous beauty Youtuber James Charles (unsurprisingly) had an absolutely flawless face for his prom. Just a few years after launching his makeup channel, Charles already has millions of subscribers.
Aside from his makeup, he kept his look simple with a black suit. His date’s bejeweled black dress coordinated well with Charles’s look, and the two looked ready to have a fabulous night!
Comedian Lily Singh has used her family background as rich material for her skits. And here she was full-on representing her Indian heritage for her prom.
Lily sported a beautiful Fuschia sari, an abundance of bangles, and a bindi on her forehead. The look was completed by complimentary Fuschia-toned jewelry.
The actor wore the traditional tux for his big night, but Kroll’s hair was another story! He decided to keep his hair long and wild for prom, but at least he kept the rest of his ensemble traditional-which included a corsage.
But what really stands out in this photo are the smiles that say they were having a great time.
Actress Yara Shahidi took off to prom in a stunning yellow dress with her cousin by her side.
The strapless dress with a pleated skirt was very complimentary next to her cousin’s Fuschia one. Shahidi kept the overall look classy with minimal jewelry and left her hair naturally beautiful.
The “Kissing Booth” star chose a striking black and white dress for her high school prom. Joey posted a photo on Instagram of her playful, knee-length dress alongside her friend, and the two had some special accessories.
The girls each had a piece of fried chicken on their corsages made, especially for them by none other than KFC.
In this fabulous 70s photo, the former president wore a white suit, dark shirt, and light blue tie for his prom.
He also decided to add a lei for an island touch, but since Barack attended high school in Hawaii, the look wasn’t out of place in any way.
We bet you’re guessing that Gwen Stefani was cooler than you in high school, and guess what? She was! At age 17, she went to prom, showing off her Grace Kelly-inspired gown and a cute bob at her high school prom.
This casual yet elegant look was a pre-No Doubt look, and we have no doubt that Gwen Stefani’s style has changed drastically over the years. Though these days, she’s seemed to return to her roots.
Candace Cameron Bure
This photo looks like it was taken on the set of “Full House,” but it was actually Candace’s real prom photo! She actually went to prom with none other than her on-screen boyfriend (Scott Weinger), who played Steve on the “Full House” sitcom.
Candace looked beautiful in a classic, black spaghetti strap dress, and Scott went all out with his silk-collared tux.
Award-winning actress Kerry Washington said she had attended a few proms (and therefore had a few dresses). But for this particular prom, young Kerry chose a colorful, flutter sleeve dress.
The floral print and empire waist were refreshing touches for the time. But honestly, Kerry looks like she has hardly aged!
The Australian animal lover said that Australia doesn’t really have prom, but Bindi was still able to attend the event with her then-boyfriend Chandler Powell.
She went with Chandler to his prom in Florida and chose an elegant yet fun short, black lace dress. Bindi was all smiles that night and what makes the story better is that she and Chandler had a true fairytale ending and are now married.
Rated as the most influential teen in 2015, you can bet your bottom dollar that the “Girl Meets World” sensation had a prom, and boy (or girl) Did she look lovely. Even in that very unconventional dress.
Though it looks like some combination pom-pom and lace creation, the young actress looks ready for a big night out as she poses in front of a gorgeous sunset. Her date isn’t anywhere to be seen here, but who needs ’em.
Yes, before she was accompanying her hubby, AKA, once the most powerful man in the world to stately events, she was just a girl in high school doing high school things. Attending her senior prom was one of them.
It would be adorable if that was Obama by her side, but alas, the girl had a life before him. Here we can see America’s queen-bee-to-be sitting in her thrown dressed in gold from head to toe. Fabulous.
“A piece for Gretchen Wieners, a partial Spring Fling Queen. A piece for Janis Ian…” Sorry, sometimes it’s hard not to confuse movies with real life. While we all know how Cady Heron’s prom ended up, Lindsey Lohan’s looked a little different.
She’s no prom queen hero, just a regular girl in high school enjoying the special event with her friends. To be honest, that is way more relatable. While this photo isn’t the greatest quality, it looks like she’s having a good time.
Shailene Woodley was a Hollywood teen dream girl for quite some time. However, we’ll admit that the “Fault in Our Stars” actress looked a little different back then.
With her date towering over her and that shy smile, it’s hard to believe that she would go on and be a pretty big actress, as well as a serious political activist.
Looking at teen Snoop, one has a hunch that he would grow up to be a force. That “don’t mess with me” swagger has certainly carried him through the years, making him a hip-hop legend.
The young couple with matching corsage and boutonniere look seriously ready for their big night. When Snoop wants to, he can really suit up.
By the look of those puffy sleeves and that strawberry pink dress, the star of “The Real Housewives of New York City” enjoyed her prom in the 80s
The reality star toned her look down in later years and evidently also eased up in front of the cameras. With that slouch, young Bethany may have been a little nervous.
Tracee Ellis Ross
The year was 1990, and young Tracee Ellis Ross was ready for the prom! The actress shines in this simple yet gorgeous grey dress and dangly earrings, proving that it’s not all about the bows and frills—pure class.
To think that proud mama, the great Diana Ross was possibly behind the camera snapping her little girl is a wild thought in and of itself.
“My So-Called Life” depicted a slightly different teen from the one pictured here. Ditching the auburn hair, grungy plaid shirts, and teen angst, Claire Danes looked perfectly sunny on her high-school prom.
Her hunky date looks like he could have also made quite the TV career himself. He’s definitely the guy walking around with the football jacket stuffing nerds into lockers.
This is an interesting look for Courtney Cox. While we acknowledge that this was the 80s and special concessions are made for this, the “Friends” actress sweater-dress-combination seems weird, even for then.
While she looks slightly strange, there’s no doubt that she looks very happy, especially as she holds onto the arm of her sweet date.
Our beloved star of “Will and Grace” had her fun too. With that white satin dress, pearls, and 80s wave, Messing and her date (seen here mid-blink) are ready to awkwardly embrace the sweet sounds of Cyndi Lauper’s “Time After Time.”
Who knew that years later, she’d be one of our favorite sitcom stars and a total gay icon.
Country singer Faith Hill will always look her best. With that elegant high neck dress, it’s hard to believe that this was simply her high school prom and not some early red carpet event.
While some other awkward prom photos might embarrass some stars today, Hill looks perfectly classy, just as always.
Angelina always struck us as someone who wouldn’t actually go to prom, but this photo proves us wrong! Not only did she go, but she went all out with the lovely satin dress and an intriguing chunky necklace.
Who knew that once upon a time, this was Hollywood’s bad girl. We suppose things changed in later years because here, Angelina, she looks simply angelic!
You can’t get any cooler than this. Angela Basset and her date do not look like they’re in high school at all, though that marching band trombone brings us back to those high school days.
We simply love that 1970s cool, big hair, bellbottoms and all.
Magic Johnson here is killing it. At almost 7ft tall, the then basketball legend-to-be looks simply dashing. His date definitely thinks so too.
We love that frilly shirt and huge bow tie. Weirdly, his date is sort of dressed like Mrs. Claus. An interesting choice, though the two look wonderful.
As the frontman of the rock band “Maroon 5,” there’s no doubt that Adam Levine has swagger (and the moves like Mick Jagger?) Even in this classy white suit, we see a slither of bad boy future ladies man coming through.
His alt-girl date certainly seems to think so. In any case, this too-cool-for-school-probably sneaking cigarettes-in-the-bathroom high school couple rocked those traditional prom outfits.
Speaking of rockers, Stevie Nicks was roughly “at the edge of seventeen,” pictured her at her senior ball in the year 1966. However, it seems that she wasn’t as hip as she was in later years.
The same goes for the gentleman with the huge grin. That woman would soon be killing it as the face of “Fleetwood Mac.” Before that, it was all flowers and tiaras.
The queen of southern cooking has managed to more or less hold onto the same hairstyle for all these years. Only now, it’s silver (which is kinda cool.) Strangely, the southern bell looks a little like young Elizabeth Taylor here.
It sure is a classy look, and her date looks equally dapper. We must say we are enjoying the sweet romantic moment between these two ‘youngins.’
First off, we love Bruce with hair. It really changes a lot. It is still pretty strange to see him pose for his high school prom photo, but, as we can tell, he had a whole other life before he was chasing baddies in a white tank top.
Still, there’s something about the look on his face that tells us danger is around the corner. Any minute now, he’s going to carry his date to safety through some very cool explosions.
No, that is not a young Barak Obama. That’s an even younger Bruno Mars at his senior prom. We suppose the lei is a standard for proms in Hawaii. He is a native of Honolulu, after all.
Bruno’s casual pose really sets the tone. The super-smooth singer oozes cool. We’re sure that he was full of awesome dance moves that night.
The golfer certainly brought his A-Game to his high school prom. Looking dapper in his tux, smiling beside his lovely date, Woods’ smile is so wide; you would have thought he just won the PGA.
The athlete’s date also looks really sweet. We wonder how long they lasted after that picture was taken.
It’s hard to believe this isn’t from a photoshoot from an early 90s “Vogue” cover because Tyra Banks just looks as chic as anything. To be fair, the fashion icon did start modeling at age 15.
The earrings, the dress, the hair. Here, Banks proves that even though she spent many years modeling other people’s clothes, the style is all her.
The golden boy of the E! channel, Ryan Seacrest, is all about exposing the real lives of countless stars, so it’s only fair that we get to see a glimpse of his. Unfortunately, there’s nothing particularly juicy over here.
Just Seacrest’s camera-ready smile and perfect hair. And with that grin, his date looks starstruck before all the stardom even happened. Sometimes you just know.
Unlike other stars on this list, “Stranger Things” star Caleb McLaughlin had his prom not too long ago. In fact, we’re surprised it happened so soon. Just the other day, the kid was cycling around the burbs making a fuss about ‘the upside-down.’
Well, time flies, especially when you’re binging three seasons on Netflix. In any case, it’s great to see Caleb out of the 80s gear and looking dapper in something very 2020.
Kobe Bryant and Brandy
Rarely do we see two stars in one picture! The legendary Kobe Bryant will never be forgotten, and seeing this photo gives us all kinds of feelings. The two were high school sweethearts and, of course, went together to their senior prom.
Brandy’s gorgeous champagne dress and stylish clutch tell us that she had star quality even then. The beautiful R&B singer and legendary basketball player must have been the envy of the whole school.
The daughter of ABC queen Kelly Ripa and soap star Mark Consuelos, Lola Consuelos had her prom, and she looked simply stunning in that green satin dress.
It’s great to see the proud mama Kelly Ripa stand beside her. With her parents’ background, we assume that Lola might eventually make her way to the screen. Here’s hoping!
Scarlett Johansson and Jack Antonoff
Scarlett Jo has had a fascinating dating history, and this photo might be the start of that journey. Here she is with her prom date Jack Antonoff, the guitarist and drummer of the band “Fun.”
Years later, he would find love (as well as heartache) with Lena Dunham, and she would go on to star in a string of blockbusters as well as date many Hollywood hunks. But in this photo, they’re just two teens enjoying their senior prom.
Honestly, this candid photo of Sandra Bullock and her hunky date at their school dance looks as if it’s a scene from a typical Sandra Bullock rom-com, but, alas, this is totally real life.
This “Miss Congeniality” star can make anything look cinematic, even when she was just a teenager in the middle of an awkward slow dance.
Janice Ian’s look wasn’t terribly far all from the real Lizzy Caplan in her high school days. She was definitely rocking that heavy 90s alt-girl look. These two were definitely rolling their eyes through the whole event.
Even if the cool blue-haired couple did go “ironically,” we are loving the funky get-up and certainly appreciate the effort.
During his “Twighlight” days, Taylor Lautner was once one of the most crazed about teen actors in Hollywood, so we are definitely enjoying this throwback image of the actor in his high school years.
We love that classic 2000s hedgehog hairdo that little Lautner is rocking. It’s hard to believe that just a few years later, he’d be the hottest werewolf in cinema history.