#30. Fergie
Fergie, Black Eyed Peas member, chose an extravagant look for her prom night. I bet she had all eyes on her because she did look gorgeous, but there was an excess of accessories. She wore a big necklace and elbow gloves. The fact that they were matching doesn't justify her bad choice.
The dress had pearls on top of it, and she was wearing shiny earrings. She left her beautiful blond hair loose. Fergie firmly believes that she was following the fashion trend of the early 90s. We totally agree with her, but her look was quite excessive. Even if she had an excess of fashion, Fergie looked amazing!
#29. Brad Pitt
It's impossible to dislike a 70s look, considering who's wearing it. Brad Pitt wore a baby blue suit. He was very handsome (and still is) but there is a slight detail that we can't miss: that weird tie. Was it trendy? We doubt so. As for her date, she wore a vintage white dress.
If you dare to wear these outfits nowadays, you'll certainly call everybody's attention (for worse). But back in the 70s, they totally rocked! Brad's haircut was suited for that time, but we still prefer his actual and attractive look. The older he gets, the better he is!
#28. Demi Lovato
There is one not-so-vintage celebrity prom photo. Demi Lovato was already famous when she went to prom, due to her role in Camp Rock. She was in a relationship with singer Joe Jonas, but she decided to go to prom with a friend, just to keep an old promise.
This picture is from 2010, not so long ago. Demi wore a beautiful strapless dress, which suited perfectly, and big shiny earrings that matched. Noan, her friend, wore a black suit with a stripped shirt. Their looks were impressive! Though they weren't matching, it can't be denied that elegance was by their side.
#27. Elle Fanning
Another not-so-vintage photo, here Elle Fanning's dress is just too perfect to be true! We bet Elle dreamed about this dress her whole life, because it couldn't be cuter. There is a lovely story behind this picture. Unfortunately, Elle didn't have a prom night. Instead, she was at a red carpet.
Elle was working to promote her movie The Neon Demon at the Cannes Film Festival, so she missed prom. She couldn't attend but her date and best friend Class went to France with her to celebrate together. We all want such a supportive friend like Class in our lives!
#26. Ariel Winter
Modern Family star Ariel Winter was in the middle of the making of the ABC sitcom when she went to prom, back in 2015. Celebrities perfectly know how to choose a red carpet outfit, as was Ariel's case, because she chose a fantastic dark dress to prom.
The famous actress wore a sensational long mermaid dress. Her mermaid outfit and red hair made her look just exactly like The Little Mermaid, what a coincidence! Ariel was very attractive, a total diva! We believe she chose an outfit that could show off her sexy curves, and we love it.
#25. Meryl Streep
Coming across this old vintage look wasn't that bad. In fact, we believe that actress Meryl Streep was suited for the occasion! She was wearing a long white dress. Maybe the most shocking part of her look were the gloves. They look awkward because they don't cover her elbow, why are they so short?
Meryl's date was well suited, too. He wore a black suit and a bow tie, nothing out of the ordinary, but still great. We believe classics are always trendy. In fact, the couple did a perfect match! If only that man knew that his date would become a great actress one day!
#24. Ashton Kutcher
The That '70s Show star had a great time at his prom. Ashton Kutcher has always been incredibly funny and talented, and the picture is proof of this. He chose an elegant look to prom, but definitely the best part is his hairstyle! It's sexy and cute.
Ashton's attractive outfit and great dance moves called everybody's attention on the dancing floor. He was so into it that he took off his jacket and showed a fantastic outfit. We wonder what his date chose that day, but we guess that they made a perfect match.
#23. Ellen Degeneres
What we are seeing now is an anti-Ellen outfit. Certainly, people change over the years and Ellen changed for good! She left her old-fashioned hairstyle and weird dress to dress with elegance every day! Our favorite comedian of all times chose a long dress with a controversial pattern.
Ellen's hair was a trend back in the 70s. She was matching her date, since they both wore red colors. The couple made a risky choice but they totally rocked! What's funny is that, in 2015, Ellen invited her date to be on the show to discuss their prom outfits and their weird choices!
#22. Beyoncé
Long before she was known for her great hits, her excellent voice and coreographies, Beyoncé was just the daughter of a sheltered cleric in Texas. She went to prom with Lyndall Locke, her boyfriend at that time, someone who doesn't deserve our attention because he cheated on her!
However, Beyoncé gave him the fan's attention, because she was inspired by her sad experience with him to create Lemonade, one of her greatest hits. Back to her prom outfit, some fashion experts may say that it was quite awkward because it had weird swirls, but she was sensational! And so was her disgusting date.
#21. Jimmy Fallon
The great comedian and Saturday Night Live host has funny memories of his prom. Here we don't have anything to say about his outfit, which was perfect for the occasion. Jimmy wore a black suit and his date a pink dress that was a sensation back in those times.
Jimmy's date was wearing white gloves and white tights, which matched Jimmy's... skin! He was as white as snow. When he was asked about that day, he said "my date didn't tell me she was getting a tan and high heels for the prom. Standing next to her I looked so pale and so small." A night to remember!
#20. Gigi Hadid
Model and influencer Gigi Hadid is one of the most iconic girls of this decade. She always appears in many fashion magazine covers and wears stunning looks. Not so long ago, Gigi chose an attractive look for her prom night. She was wearing a short coral dress, showing off her beautiful long blond hair.
Of course it was a trendy look, but it wasn't striking. It certainly wasn't an ordinary prom dress, but she could have chosen a more impressive outfit. We are used to seeing her in the spotlight, wearing sensational outfits. However, if we compare her style back in 2013 and now, we reach to the conclusion that she is always sparkling!
#19. Tom Brady
Tom Brady looks younger than he was in this picture. Now married to Gisela Büdchen, one of the beautiful models working for Victoria's Secret, he has always had a great sense of fashion. He was so young when he picked his prom outfit, which suited perfect!
The best part of these vintage photos is when celebrities admit that those were different times and are able to accept that their outfits may be now embarrassing, but back then they were cool. The NFL Superbowl champion shared this picture on Facebook and wrote, "Who's ready for the weekend?! This guy is!"
#18. Jennifer Aniston
You might be thinking that this picture taken from a Friends episode, but the truth is that it's Jennifer Aniston's prom night. She wore a strapless black dress and her overall outfit was amazing! However, we are having some trouble with her hair.
Maybe she didn't even care about her hair back in those days. Or maybe this picture proves that Jennifer's hair requires hard work and preservation. Even though she was hairy that night, she was stunning (as always). She added to her look a beautiful tiny earrings and a delicate necklace.
#17. Lance Blass
This is definitely one of our favorite vintage pictures because the couple totally rocked! Danielle Fishel, who appeared in Boy Meets World, chose an amazing white dress to prom. Lance Blass also made a good choice, look at those pants! They aren't ordinary and they look great on him, with that fine line at both sides.
This couple dated for two years. At first, they thought that Lance would miss prom because he was on tour at that time. He was far away from home, in Japan, when Lance sent Danielle flowers and a letter telling her that they would go together to prom. Lovely!
#16. James Charles
Youtuber and beauty icon James Charles made a great impression at his prom. Just five years ago, James created a Youtube channel where he shares beauty tips. He became rapidly known and now he has millions of subscribers. Fame knocked on his door, because James was at the Met Gala!
James went to prom a few years ago, in 2017. He was wearing a black suit, and his date was matching with him! She also wore black with shiny strass on top of the dress. Definitely, the best part of his look was his make up. He had a dark eye shadow, red lips and contour. They were fantastic!
#15. Natalie Portman
Actress Natalie Portman got into the Hollywood world at a very young age. When she was just 13 years old, she appeared in Léon The Professional. Natalie never left this world, so her adolescence was publicly known. It was in the middle of the 90s that she went to prom with a wonderful sky-blue dress.
It was a great dress for that time, full of glitter on the top of it. She wore a shawl (so 90s) and a silver glitter handbag. She rocked with her hairstyle and make up. Being a celebrity at such a young age demands perfection at all times, even at prom.
#14. Matthew McConaughey
We give extra points to this couple, who did the perfect match! No one took the risk, the rest of the couples just matched colors with boutonnieres and flowers. Matthew McConaughey's vintage picture is the only one that shows that he dared to wear accessories that matched his date's dress. His dress was wearing a blue dress and he wore a blue bow tie.
The actor was wearing a black suit and his date chose a dress that was super trendy back in those days. The interesting fact about this picture is that Matthew is wearing a bracelet while his date wears a watch! They couldn't be more perfect.
#13. Jessica Alba
The Fantastic Four star chose an adventurous dress to prom. Jessica Alba looked just like a Disney princess, in fact, she may have borrowed the dress from Snow White! To complete her fairytale look, Jessica placed tiny flowers on her hair, which gave the impression that she had a crown.
Jessica's prom date should have wore a more prince-outfit, but he decided to keep it simple because he was wearing a white shirt with a white bow tie and a black suit. Although the couple didn't quite match, they both look lovely in this picture, especially princess Jessica.
#12. John Stamos
Can you recognize who is this adorable guy with long brown hair and a prince-like suit? Believe it or not, this is actor John Stamos, who starred Full House. It was quite hard to guess, since he had a completely different for that movie!
John went to prom in the 70s. He wore a white suit with a big bow tie and a disarranged shirt, making him look like a Disney prince! His date got her hair done, and it was perfect. Although this vintage picture is really cute, we believe that John's hair in Full House is the best choice he ever made.
#11. George Clooney
Back in the 70s, everybody was concerned about fashion, and so was George Clooney. Apart from his baby face, George wore a grey suit to prom. To make it more fashionable, he made some additions to his outfit. George completed his look with a huge bow tie and a messy shirt.
His date was wearing a white dress with a big yellow pin, a gift from George so they could match colors. Certainly, George was drawing every girl's attention. Not only because of his outfit, but also for his young face. His pose is proof of this. He has always been a good-looking man.
#10. Will Ferrell
The Stepbrothers star made a good impression at prom, because he chose to wear a tiara on his head! It seems that he was making jokes since he was born. Will Ferrell always knew who to make people laugh, both at him and with him, so he wouldn't miss such a perfect occasion to have some fun.
Will's date was wearing a black dress with pearls on his necklace and earrings. She had a big smile on her face, so she must have enjoyed Will's company. Who wouldn't? The man who gave life to famous comedies Anchorman and Elf had more to offer than just a good-looking outfit.
#9. Carrie Underwood
Before Carrie Underwood jumped into fame with her amazing country hits, the signer was nothing more than a teenager who lived in a small town in Oklahoma. She went to prom wearing a strapless dress. Carrie had a beautiful hairstyle, she decided to leave her curls behind by pulling her hair backwards.
If we talk about splendor and taste, Carrie's date was totally matching with her. He was wearing a black and white suit with a black bow tie. By looking at this vintage picture, it's easy to tell that the couple had an excellent time together! And Carrie wins for having the best vintage hairstyle.
#8. Harry Styles
If we think about a man who nowadays sets a trend is definitely Harry Styles. He couldn't have a more suitable surname, because this guy is a teen icon! Harry, ex member of One Direction band, wore an ordinary prom outfit back in those days, except for his hair.
At prom, Harry was wearing a typical black suit with a haircut that looked exactly like Justin Bieber's. In fact, that haircut was super trendy at that time, so we are not going to judge here. The girl she was with wore a white dress with a yellow accessory that matched. They were lovely!
#7. Kim Kardashian
Before plastic surgeries and millions of followers on Instagram, Kim Kardashian was just a normal (but privileged) teen girl. Kim wasn't famous when she went to prom (lucky her!). Her sisters Kendall and Kylie Jenner didn't enjoy the same privilege. The fact that she was paying little attention to glam was evident.
Back in 2000, Kim wasn't as glamorous as she is today. She had a curly hairstyle and soft makeup. Her prom dress wasn't extravagant, she just looked elegant and simple. Now she wears only dresses made by well-known designers, like Givenchy. Most probably, she may be using her prom dress as sleepwear.
#6. Reese Witherspoon
Genes may freak you out, because this girl in the photo could perfectly be Ava Phillipe, but it's actress Reese Witherspoon at prom. We can barely see the difference between mother and daughter, maybe because of her arranged hairstyle and dark lips. From Elle Woods' point of view, this outfit would be totally approved.
Reese chose an elegant look, she certainly is the best dressed of our list. Even though Reese and her oldest daughter, Ava, look like the same person on the outside, they are quite different on the inside when it comes to outfits. In 2018, Ava decided to add color to her prom outfit, because she wore a yellow dress and her hair was loose.
#5. Jaden Smith
Jaden Smith, son of actor Will Smith and Jada Picket, went to prom just a couple of years ago wearing a stylish look. Both Jaden and his date chose a total white outfit, and they couldn't be more perfect. His date was wearing a mermaid dress with ear drop earrings and a beautiful hairstyle.
Jaden was wearing the same outfit that he wore at Kim Kardashian and Kayne West's big wedding. The fact that the celebration took place in a completely different continent doesn't mean that he repeated his Batman outfit, because he added a jacket and a tie to make the difference. Isn't it super original?
#4. Blake Lively
When we think about the couple who has the most fashionable looks, Blake Lively and her husband and actor Ryan Reynolds are the ones who first come to mind. Back in 2000, Blake's prom outfit was top trend. Fortunately, we left this trend behind. Her look was quite good, she resembled a princess wearing a pink dress with glitter all over it.
What is quite striking for us, looking at the picture 20 years later, is that little tiara she was wearing. As for her hairstyle, it wasn't so bad except for the weird fringe. What matters most is that she seemed to be having fun that day, and she certainly enjoyed her outfit.
#3. Taylor Swift
Our favorite country-pop singer Taylor Swift was quite classic at prom. Before she became a teen celebrity and reached fame, Taylor was just a small town girl, like she said in her White Horse lyrics. Taylor is known for being constantly reinventing herself in order to be trendy, but it was not the case at prom.
Taylor wore a white strapless dress, which completely matched her date's outfit, who wore a total white outfit: white suit, white shirt and a white cap. As Taylor always writes about her past, it's interesting that she totally skipped this episode of her life. We truly believe that this outfit deserved to be in one of her songs.
#2. Lady Gaga
Lady Gaga's prom outfit is certainly shocking. Not because of the outfit itself, but for the striking difference with her actual style. After 20 years, she looks like a completely different person. Lady Gaga is well known for her scandalous looks, mostly on red carpets, which totally differ from her prom night.
Gaga wore a sky-blue dress which fell just on her knees. She was matching her friends, since most of them wore pastel colors, a trend of that time. What definitely wasn't a trend was that white limo behind them... really? The 2000s fashion was a total mess, but we firmly believe that Gaga got away with it!
#1. Britney Spears
The Queen of Pop and famous singer Britney Spears looked stunning with a red long shiny dress at prom. She arranged her hair and showed off her curls. It was a time when everybody wore crazy and ridiculous outfits, but Briney stood out for her excellent choice. She didn't add any accessory, which is great!
Britney was born with talent, though nobody new at that time. Just a few years later, everybody would know what she can do. Her pose says a lot about her, though no one thought that she would later become a pop star with millions of fans all over the world! We love you, Brit!