The 15 Most Embarrassing Celebrity Prom Photos

I don’t know about you, but there are times I go through old photos and try real hard not to throw up a little in my mouth. You have to admit to yourself that some of those photos from back in the day can be absolutely cringe-worthy. You think why on earth did I wear that, and my hair, was that really in style back then? When you think of your prom days, you can’t help but appreciate the times, and the horror stories they brought to your sense of style. Of course back then you thought you looked cool and it isn’t until you look back on it that you shudder in disgust.

Thankfully we mere mortals aren’t the only ones that have horrific prom photos; in fact, celebrities have to deal with the same photos. It may even be worse for them being in the limelight, forced to be gorgeous all the time only to have old prom photos leaked. Whether these celebrities were popular or not it does not save them from the embarrassment of the outfits they wore - and, God those corsages! These embarrassing photos will never leave the internet, and like the rest of us, these celebrities will have to live with them. Check out these embarrassing photos of celebrities at their prom!


15 Jennifer Aniston

via theCHIVE

We love this girl, and she rocked her career on the TV series Friends but there’s no doubt about it - this picture is horrific. The black dress isn’t too bad, in fact wearing black is probably the safest thing you can do because black is always in style. Her hair though is something else entirely. Aniston has admitted that she went through an awkward stage before she became one of the hottest actresses in Hollywood. She struggled with her weight and always had trouble staying in style. In this case, her date was feeling just as awkward as she was. I wonder how he feels knowing that he used to date a celebrity that has been linked with Brad Pitt. She’s certainly not feeling awkward these days with a successful career and a boyfriend who adores her and although she is over 50 now she appears not to have aged, and her body is as exquisite as always.

14 George Clooney

Via Elle

Oh, that long hair! We can’t deny that George Clooney was always a handsome guy, but he looks darn right goofy in this picture. These days he looks suave and debonair especially with the gray locks he sports. However, he wasn’t always as slick as he is today. He must be reminiscing about his own youth these days as he was recently seen playing basketball with a boy that happened to be the son of the girl he took to prom once upon a time. Awwwwww! "Guess who just called me and asked if Brent could come to St. Augustine school and play basketball? My old friend George Clooney,” Laurie Laycock posted on her Facebook wall. “He said he had kept up with Brent's basketball and was very proud of him and wanted to play him a game. Still the same old George!! It was nice that he called to say hello and to talk about Brent. He said he was going to keep up with his college games too."

13 Danielle Fishel and Lance Bass

Via US Weekly

This couple couldn’t have been sexier as a couple, but they did not save themselves from the embarrassing prom photos. What was Lance thinking with that hair? The two dated for a period of time and who could blame Lance with such a smoke show as Danielle Fishel on his arm. The couple dated for a few years and broke up in 2000. Lance came out of the closet in 2006, but Danielle didn’t seem to be shocked, in fact, she said she heard rumors long before he came out. Their friendship is still solid, however, and she considers him a great friend. “Lance and I are very good friends. I absolutely adore him, and I support him in everything he does. I actually went to go see him dance at Dancing with The Stars a couple times.” Nothing seems to stand in Danielle’s way when it comes to supporting the people in her life and Lance is certainly one of them.

12 Blake Lively

Via Go Social

Yes, even Mrs. Deadpool cannot go unscathed when it comes to horrific prom photos. This stunner is huge into the fashion world with many designers that consider her their muse. She is considered to be one of the most stylish young female actresses in Hollywood today; she even sports some of the sexiest maternity wear that I’ve ever seen. In this photo, however, she wouldn’t be considered a fashionista by any means. The pale pink dress filled with bling is much too sweet for our taste and that crown... The tiara used to be quite popular when it came to preparing for the prom, but it’s not something you see much of anymore. Although us ladies always love to feel like a princess, these days the tiara is considered to be overdone. Sorry Blake, this prom outfit is one that was a complete fail.

11 Rihanna

Via Teen Vogue

These were the days long before Rihanna ever met Chris Brown and delved into the controversy that would shape her romantic life. In this picture, she appears to look awkward while standing with her date for prom. It might have something to do with the tacky corsage that she is donning that night. Recently Rihanna was caught Tweeting about another girl's choice of prom outfits on Twitter, which is weird considering her look wasn’t exactly runway worthy. Alexis Carter created a low-cut green dress that had wings, a dress that was inspired by one that Rihanna once wore. Many people continued to share the original post spawning the hashtag #PromBat. Then Rihanna caught wind of it, and she started to make fun of it. She posted a side by side view of her dress against the one that Carter made and added a sad emoticon face to make the situation even more brutal.

10 Adam Levine

Via Jelly Share

Both Adam Levine and his date look like they are dressed for the next vampire movie. Why are you guys so pale? It’s as if they are both wearing costume makeup. She looks like she is about to get married while Levine looks nerdy in a white suit with a black bowtie. The suit is epic in the sense that it looks like something that Jeff Daniels would have worn in Dumb and Dumber. The suit had coattails which are certainly something you don’t see at prom very often. It’s hard to imagine the hot, tattooed rock star from this picture but he’s got to be in there somewhere. He looks as if he might be too young even to grow the beard we see on the right-hand side. Despite the horrendous picture Levine moved on to be a popular musician and dates hot girls all the time.

9 Angelina Jolie

Via LifeBuzz

It definitely took Angelina Jolie awhile to grow into the beauty that she is today. Men for many years have hailed her as one of the sexiest women alive, and she was able to steal Brad Pitt from a seven-year marriage to Jennifer Aniston. When she was younger though she went through an ugly duckling period; though that didn’t stop her from any of the weird behavior she was part of growing up. In this prom photo, there is so much wrong that it’s hard to zero in on just one thing. She looks almost like a child bride because of the white dress and bouquet of flowers. Talk about a large corsage. But if that isn’t bad enough, she has this bulky necklace and plain Jane hairstyle. What’s the most shocking part is that her parents are Hollywood veterans and it appears as if there is no wealth behind her outfit at all?


8 John Stamos

Via theCHIVE

John Stamos has always been considered a heartthrob in Hollywood, and it’s produced a successful acting career for him. He’s been known for his head of hair especially during his time on Full House when he used to care for his locks like they were one of his children. He’s never been afraid to leave his hair long, and it’s not something that has ever hurt his career in Hollywood, in fact, it probably improved it. Even in his prom photos, it proves that he always loved that hair. There’s no denying however that he was always easy on the eyes. He also proved that sexy men can wear ruffled suits, though the case could be argued that they probably shouldn’t. John Stamos, however, is not ashamed of his prom photo, in fact, he posted it on Instagram recently captioning it with, “#TBT, #Prom, and #Hair.”

7 Taylor Lautner

Via Smosh

It’s hard to imagine the guy in this photo having the rock hard abs that he donned in the Twilight series. In fact, the guy in this picture would have a hard time inspiring the Team Jacob craze. Taylor is looking particularly dorky with really spiky hair and a button down shirt. It appears as if the actor decided to forgo the suit for prom and just wear a dress shirt. His date is wearing a tiara just like Blake Lively donned and it’s not helping the situation. He’s got that winning smile, however, and that’s what got him to Hollywood. Lautner grew up in Hollywood however, being a child star first before getting his big break in Twilight. So dating was probably always an awkward stage for him. It can be hard for any actor to date while working so imagine how difficult it must be trying to get a prom date for a kid in Hollywood.

6 Elizabeth Banks

Via Zimbio

We can’t get enough of funny girl Elizabeth Banks; she has made a career in Hollywood through a series of comedies that had laughing. She was the star of Pitch Perfect and even went on to direct the sequel. Her prom photo shows a fresh-faced girl holding a bouquet of flowers. She is wearing the typical prom dress with a little bit of bling and oh that hair is definitely from the 90’s. The picture was taken during her prom in Pittsfield, MA. Her prom was in 1992, and that night she was voted prom queen. We congratulate you Elizabeth Banks on your prom queen honor, but you must still go down with the rest of us for another silly prom photo.

5 Jimmy Fallon


Jimmy Fallon has been very candid about how geeky he was in high school, and judging by his prom photo we can’t agree more. For a geeky guy, he still seemed to score a very pretty date for the prom, and we give him kudos for that. Although he’s wearing the standard black suit, you can’t deny the awkwardness of the picture. His skin is blazing white, and his hair seems to have a mind of its own. He’s a hilariously funny guy though that certainly has no problem poking fun at himself. Recently he and The Rock did a sketch together where the two of them went to prom together. Again it’s pretty obvious that the star has no problem laughing it up with friends and making fun of one another.

4 Fergie

Via StarCrush

Fergie is definitely all about being “Glamourous” and stylish in the fashion world. She is a highly successful singer that was made famous due to the band Black Eyed Peas. In this particular prom photo, however, she looks more like a pageant queen getting ready to go out on stage donning “formal wear.” She would have truly been the glamorous one that night, and despite the terrible dress that face is as striking as always. In 1993, she was voted junior princess in Hacienda Heights, California. These days Fergie is working hard on her own music. She is set to release her new album, “Life Goes On” in 2017. Regardless of her prom photos and the extra laugh we get when we look at them, the girl has certainly gone places, and we love her music.

3 Julia Roberts

Via Jelly Share

Julia Roberts is one of the most famous and beautiful actresses in Hollywood. She was a bit flighty in high school, never had much interest in going to class, but I bet the guys were just dying to take her out on a date. That smile, after all, must have sent them all chasing their tails. She always had that crazy hair that always seemed to have a mind of its own. Recently, she was on Jimmy Fallon, and he showed a few of his guests their old prom photos embarrassing them. I told you he was into that sort of thing and he probably showed his off as well. Julia Roberts was shocked to see her photo and got a good laugh out of it. Julia Roberts was 46 at the time, and it must have been a blast from the past for her.

2 Tyra Banks

Via Jelly Share

Va-va-voom! Tyra sure knew how to pull out all the stops when it came to this dress. My God girl, she sure doesn’t look like she belongs high school. Tyra is from the fashion world, of course, she’s spent her career modeling for some of the biggest names in fashion, so although the picture is funny, the dress is to die for. Tyra has since spent her time working on her show ANTM as well as The Tyra Banks Show. She invited an inspiring designer onto her show recently because of a dress she posted that almost broke the internet. “I am such a fan of you. I saw you on the Internet, and you blew me away with your talent, with your beauty,” Banks said. “This is the beginning of your journey and becoming the force that I know that you can be in the fashion world; this is not existing in the fashion world right now, and it is desperately, desperately needed.”

1 Taylor Swift

Via Mirror

This hilarious prom picture shows that Taylor Swift has always been a fun and quirky person. I’m not sure why anyone allowed her boyfriend to wear the gangster hat for prom but we’ll try not to look at it. It’s not every day you see gang signs by two people who live in the suburbs. Maybe the reason why the picture seems so silly is that the date between the two was platonic. “In my sophomore year (of high school), the place to hang out was the volleyball court. That’s where I got asked to go to prom by a guy named Cody … It was two days before prom, and both of us were dateless. So I was sitting there on a bench next to him, and he was like, ‘Well, my girlfriend broke up with me.’ And I was like, ‘Well, my boyfriend cheated on me.’ And he was like, ‘So, you don’t have a date for prom any more?’ And I’m like, ‘Nope, do you?’ And we both just looked at each other, and he said, ‘Wait a second, I need to make this special.’ So he gets a stick and draws in the sand: “Prom” — and then a question mark. And I said, ‘Yes! Of course!’ It was the most fun prom because we were just friends, and it was so spontaneous.”



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