Celebrities always look glamorous, especially when they step out on the red carpet. You’re used to seeing them in designer duds, professionally coiffed hair and makeup applied by expert artists. It’s easy to look glam with an army of stylists by your side! But did you ever wonder how these celebrities looked at some of their earliest formal affairs?
Some are dated, some are tacky, and some are impossibly stylish even then! Check out some of the best and worst celebrity prom photos of all time.
Britney was a teen sensation who was no stranger to publicity by the time she attended prom. She actually graduated high school via distance learning so she could continue to tour. It’s no surprise that she looks on point in her prom photo, despite the dated glittery gown.
Natalie Portman was already famous and successful long before high school, but the actress has famously always put higher value on her education. When this photo was taken, she was Harvard-bound and still had an exciting acting career ahead.
Brad Pitt has been named Sexiest Man Alive more than once, but it’s safe to say he has made some interesting hair choices to balance out his natural good looks. Turns out that dates back to high school when he sported this ‘do in the early 80s, along with a pale suit. Still, his date seems overjoyed to be by Brad’s side.
Meryl Streep’s prom was a long time ago, nearly a decade before her film debut. She would go on to be nominated for a record 21 Academy Awards. Back in high school, she was bursting with star power even in this simple dress.
Harry Styles’ career took off when he appeared on British televised singing competition The X Factor when he was just 16. It was there that he was connected with the other members of the band that would become One Direction. He remains friends with his prom date Lydia Cole to this day.
Rihanna grew up in Barbados, and actually didn’t finish high school since her music career was starting to take off. She got her chance to attend prom, and make this fan’s day, week, month and year, as part of MTV’s Once Upon a Prom celebrity prom date show.
Reese Witherspoon graduated in 1994, three years after landing her first lead role in The Man in the Moon. She had some more acting chops by prom, and still graduated with top grades and got into the prestigious Stanford University.
Sarah Palin’s political persona is of the every-woman – who also happens to hunt by helicopter. She attended high school in her home state of Alaska, where her competitive streak in basketball earned her the nickname “Sarah Barracuda.”
Another Sexiest Man Alive list fixture, Matthew McConaughey became a heartthrob of romantic comedies in the 2000s and went on to more serious acting roles. Back in 1980 though, he was as goofy as a high schooler can get, attending prom with his adorably dated-looking date.
Before she was Grace on the sitcom that launched her to stardom, Debra Messing was a normal high schooler in Rhode Island. She wore a modest dress to her high school prom, but still managed to look picture perfect (at least compared to her date) in the photos.
Already on her way to a super-star future with several childhood recordings and having started Destiny’s Child. She’s glowing with optimism for her own destiny in this adorable prom photo.
We all know Miley Cyrus’s acting credits started early, and her family fame preceded her. With her busy filming schedule she didn’t attend regular high school but instead had one-on-one tutors who would work with her on set.
Stacy Ann Ferguson, later known as Fergie, began acting and singing at 10. By the time she was ready to graduate, she was about to be signed on to her first major contract. She and her friends certainly look a sophisticated bunch!
We know Bruno Mars for his wide-ranging musical talents and funky personal style. From the looks of this prom photo, it looks like he already had the style back in 2003 when he attended prom in Hawaii. Hopefully he impressed his date with some of those energetic dance moves!
Here you see a straight-A student, star quarterback, class clown and budding style icon by the name of Eric Marlon Bishop. Later taking the stage name Jamie Foxx, he went on to see equal success as a comedian, actor and singer.
Even though this photo was taken in 1979, George Clooney’s movie star good looks are already recognizable. His date certainly seems to see it! He hadn’t been discovered yet, though he had appeared as an extra in the TV mini-series Centennial.
Blake Lively was thriving as a high school senior – class president, a cheerleader and a member of the championship choir. Her outfit is almost a parody of a prom queen – pink? Check. Sequins? Yup. Tiara? Got it. Awkward pose with date? You bet!
Kim Kardashian & TJ Jackson
We all know the Kardashian sisters were born famous and wanted for nothing in their childhood years.
TJ Jackson and his brothers, sons of Tito Jackson, also had fame from an early age.
So it seems only fitting that these two would have a lot in common back in high school. They dated for a couple years and attended prom together in what we are sure was a very lavish evening.
Ellen DeGeneres is one of the most well-loved celebrities, winning 30 Emmys and 20 People’s Choice Awards. She famously came out on national television and married her longtime girlfriend, but before that she attended prom with her male date. Those ‘70s colors!
Always looking to entertain a crowd, it looks like all eyes were on young Ashton Kutcher at his prom in the mid-90s. He’s having fun, but almost could have missed his prom after being caught breaking into his high school earlier that year and convicted of burglary.
This young star was seen on red carpets dating back to the age of 7, when she was nominated for a SAG award for her role in the film I Am Sam. After 10 years of fame, she appears to have had a relatively normal prom, seen here with friends from her Studio City, California high school.
One actor we know for a fact can clean up good is Jon Hamm. After his role on the series Mad Men, he became a style icon responsible for the resurgence of 60’s style. For his own personal throwback, we see Jon here in 1989, when he looks a little less comfortable in the tux and bowtie.
Always the comedian, Will Ferrell just couldn’t resist making people laugh back in high school, when he donned the tiara for this prom photo. His date doesn’t seem to mind being upstaged by princess Will at all, no doubt she had a hilarious and fun evening with the comedian.
Jessica Alba looks picture perfect in her prom dress, and her lucky date knows it! The actress was already accomplished, having a number of TV appearances on The Secret World of Alex Mac, Flipper, Beverly Hills 90210 and Love Boat.
Courtney Cox was born and raised in Birmingham, Alabama and graduated in 1982. She didn’t start her acting and modeling career until after enrolling in college, so she was a very normal high schooler – and from the looks of it, a very conservative one.
Sally Field is a majorly accomplished actress, with two Academy Awards, three Emmys, two Golden Globes and a SAG Award, plus numerous other nominations. Back in high school, she was a typical California girl and a cheerleader.
Tiger Woods is one of the most well known and arguably one of the best golfers of all time. He’s also one of the highest-paid athletes in the world. He was famously a child prodigy and may have already known what was in store for his future when this prom photo was taken.
Already a star in high school with The Adventures of Sharkboy and Lavagirl and his defining role in Twilight to his credit, Taylor Lautner was also the highest paid teen actor in Hollywood when this photo was taken. Taylor nonetheless looks like a regular high schooler, who played school sports and claims he was bullied for being an actor.
Demi Lovato started acting early, but it didn’t exactly boost her popularity. She first appeared on TV’s Barney & Friends and was bullied so mercilessly that she had to be home schooled. However, she had a pact to attend prom with her childhood friend Nolan, and they both look happy and glowing to fulfil that agreement.
Before Bruce Willis was an action star, he was a high school student council president with a stutter and the nickname “Buck Buck.” He also had a full head of ‘70s hair!
She made her film debut as a Mean Girl, but Amanda Seyfried and her real-life high school friends look a lot more chill. In this photo, Seyfried had already done some modeling and appeared in soap operas like As the World Turns and All My Children.
Destined to become one of hip hop’s most influential and prolific artists, Calvin Cordozar Broadus Jr. was already into rap as a high schooler. In fact, he started in sixth grade. We don’t know whether he had already developed his colorful personal style in high school, but he went with the buttoned-up look for prom, and pulls it off!
Christina Aguilera is another one of those starlets who was famous long before prom. She was part of the Mickey Mouse Club and had a few recording credits under her belt when this photo was taken, which is probably why her dress looks so sophisticated compared to her peers.
Jennifer Anniston wouldn’t become a household name until the ‘90s when she played Rachel on one of the most popular sitcoms of all time. However she already had the acting bug, with both parents as actors, and attended Manhattan’s Fiorello H. LaGuardia High School of Music, Art and Performing Arts. She does look camera-ready!
Growing up in Germany, Sandra Bullock moved to the states in high school. She assimilated into Arlington, Virginia’s Washington-Lee High School quickly, joining the cheer squad and school theater productions. She looks lovely as ever in her prom photo!
Taylor Swift started her music career in high school, causing her to transfer out of her Tennessee high school in favor of homeschooling and a more flexible schedule. She did go to prom with her then-boyfriend Brandon Borello, and, as is her habit, immortalized their relationship in song. “Tim McGraw”, “Our Song” and “Fifteen” are all about him.
Lady Gaga is famous for her outlandish outfits that always stand out from the crowd. Back in high school though, she wasn’t Lady Gaga, she was Stefani Joanne Angelina Germanotta. Her dress blends in with her peers (she’s in blue), but something tells us her personality already shone bright.
Ryan Seacrest is famous for his boisterous personality and upbeat presence both on radio and television. He was already interning at a radio station in high school and graduated in 1992. Just check out his date’s oh-so-nineties dress!