Have you ever compared yourself to Hollywood royalty and thought, "how do they always look so gosh darn perfect?" If this sounds familiar, then wallow no longer! As it happens, even the most famous stars haven't always been so effortlessly cool. And luckily for you, we've scoured the depths of the internet to find the earliest showbiz appearances of the most glamorous stars out there. Spoiler alert — plenty of them must have worked seriously hard to cultivate their ultra-chic 21st-century demeanor. It's time to delve into the A-lister archives and reveal the red carpet photos these stars might be wishing had never been taken.
George Clooney
When: 1989Where: Steven Cannell's 10th Anniversary PartyIn 1989, George Clooney was just another hard-working TV actor fresh off his stint on Roseanne. Nobody knew that he would one day be a total A-lister.
Except for maybe George himself... look at that smirk! We can only assume his low-key suit and jazzy tie were an attempt to disguise his star charisma.
Angelina Jolie
When: 1986Where: The Academy AwardsAngelina Jolie may be Hollywood royalty today — and always a vision of perfection — but this wasn't always the case. This photo, taken in 1986, shows when Angelina was still just actor Jon Voight's shy and adorable kid.
Her older brother James Haven is in the background and mom Marcheline Bertrand is just out of shot. Nothing beats a full family affair for your first red carpet!
Ashton Kutcher
When: 1999Where: Varsity Blues Los Angeles premiereWhile today's Ashton Kutcher might have somehow managed to convince everyone that he's hunky, cool, and perpetually hip, never forget 1999 Ashton Kutcher who never met a camera he didn't flash the peace symbol for. Well, if it helped him to couple up with Mila Kunis, then maybe he was doing something right after all.
In 1999, he was about one year into That '70s Show, so his star was clearly on the rise.
Emma Watson
When: 2001Where: Harry Potter and the Sorcerer's Stone premiereToday, Emma Watson isn't just a well-established and respected actress; she's also a political advocate with the brains to prove it. This 2001 picture of her at the height of her slightly awkward youth is a reminder of just how fast those darn kids grow up!
Known for her unique blend of classic and ultra-modern looks, Emma's come a long way from that purple boa and gold lamé clutch.
Britney Spears
When: 1999Where: 26th Annual American Music AwardsOops, she did it again... and by "it," we clearly mean late-nineties Britney painstakingly crimping her hair to within an inch of its life!
Long before her cycle of manic meltdowns began in 1999, Britney was just another pop star on the rise. She'd only recently taken the pop world by storm with the endlessly catchy "...Baby One More Time".
Brad Pitt
When: 1988Where: Red Heat premiereLate '80's Brad Pitt was so hunky and stylish that it's hard to believe multiple decades have passed since this photo was taken. He hit the red carpet with date Jill Schoelen, and no doubt the world let out a collective sigh that they weren't Brad's arm candy for the night!
Once a Hollywood sex symbol, always a Hollywood sex symbol.
Charlize Theron
When: 1996Where: Two Days in the Valley Hollywood premiereIt's been nearly 30 years since Charlize Theron made her red carpet debut, and frankly, she hasn't aged a day since.
Sure, the blue eyeshadow and '90s skinny brow may be a dead giveaway that this isn't a snap from the 21st century, but wow — this woman is not only an acting legend, but she must know witchcraft.
Madonna
When: 1985Where: 12th Annual American Music AwardsThere's no denying that Madonna is a cultural icon, and with good reason. Securing seemingly endless Grammys, VMAs, BRITs, Golden Globes, and more, Madge is a force to be reckoned with.
And her relatively new-to-the-spotlight self captured in this 1985 image proves she's always been that way. Who else could rock a lace corset and scruffy hair and still look the epitome of cool?
Heidi Klum
When: 1999Where: 18th Annual CFDA American Fashion AwardsThere's a reason that 18-year-old Heidi Klum bagged herself a lucrative modeling contract. Yup, she's always been a knockout.
If you need any further evidence, check out this photo of her casually posing on the red carpet. She could claim that she "woke up like this," and we'd believe it.
Cameron Diaz
When: 1990Where: Mask Hollywood premiereWhen Cameron Diaz burst onto the scene in the mid-1990s, no one could get enough of this gorgeous and funny girl. And it's clear to see why — with a smile that could thaw even the coldest of hearts, Diaz was the perfect example of girl next door goes to Hollywood.
Let's not mention the questionable '90s eyeshadow and eye-watering fuchsia kimono-style dress.
Jared Leto
When: 1991Where: Cool As Ice premiereWhen this photograph was taken in 1991, the biggest celebrity in the photo was actually Punky Brewster actress Soleil Moon Frye. Years later, anyone looking at it would have no problem picking out the real star in the shot: Jared Leto.
His enviable jawline just about makes up for the waistcoat he may or may not have borrowed from his grandpa.
Ryan Gosling
When: 2001Where: Animal Avengers charity launchToday, there isn't a woman alive who wouldn't kill to have Ryan Gosling wrap his arms around them. But in the early noughties, the best the rising star could do was cuddle up with this very sweet little pooch.
Neither the pup nor Gosling seem too thrilled to be papped, but we're glad to have seen that maybe, just maybe, we might have once had a very slim chance with the brooding actor.
Johnny Depp
When: 1980Where: The Various Los AngelesIn the 1980s, Johnny Depp quickly emerged as a powerhouse performer who would go on to be a major force in Hollywood. Before all the scandal and slander began to swirl, baby-faced Depp was just another aspiring star no doubt looking for a chance at stardom.
Papped here not long before his debut in A Nightmare On Elm Street, it looks like Sir Elton John did his bit and took Depp under his wing.
Drew Barrymore
When: 1982Where: London E.T. premiereActress Drew Barrymore descended from Hollywood royalty, so it's no wonder she has spent most of her life in the limelight.
Today she's also a successful businesswoman and mother, but back in 1982, she was just an adorable flower child with a few missing teeth. Well, an adorable child attending the premiere of a film she starred in. But still, aww!
Ben Affleck and Matt Damon
When: 1997Where: Good Will Hunting premiereHow about these two besties from Boston who totally dominated the Oscars in 1997? While both men are now seasoned actors and directors, back in the late 1990s they were just a couple of guys soaking up the fame.
Their power poses and low-key style kind of work!
Gwyneth Paltrow
When: 1994Where: 66th Annual Academy AwardsCan you believe what a total baby this GOOP mastermind looked like back in 1994? Yes, we're with you — it's difficult not to want to invent time travel just to be able to go back and ask her what shade of lipstick she was wearing.
Hey, maybe Paltrow has released a toxin-free version in her beauty line.
Ryan Reynolds
When: 1998Where: ABC Preview Announcements in New York City While present-day Ryan Reynolds is so handsome that he was actually able to bag a talent like Blake Lively, we're sorry to say it, but the same simply can't be said for 1998 Ryan. Hey, who are we to judge?
Merely observing, it does seem as though he made a serious misstep when it came to styling his hair. Step away from the wax!
Kirsten Dunst
When: 1994Where: Interview with the Vampire Westwood premiereWhen Kirsten Dunst appeared in the film Interview with the Vampire, no one could believe that someone so young could be so talented. They had no idea that this was just the beginning of what she could do.
And may we all take a moment to be thankful that the crimped hair trend has stayed in the '90s where it belongs.
Scarlett Johansson
When: 1996Where: Manny And Lo premiere receptionThis photo of ScarJo taken in 1996 is photographic proof that this born-and-raised New Yorker has always been the epitome of cool.
Even when she should have been going through an awkward phase, Johansson managed to rock hair clips and fluffy sleeves with an air of nonchalance we'd never be able to pull off.
Jack Nicholson
When: circa 1970Where: UnknownLook at that grin! It's almost like 1970's Jack Nicholson knows that, while he might continue to get older with each passing year, his ultra-cool reputation will just keep going from strength to strength.
You can't really go wrong with a slick black suit, but the bow tie is the pièce de résistance of Nicholson's circa 1970 style. As for the sunglasses, your guess is as good as ours.
Kate Winslet and Leonardo DiCaprio
When: 1998Where: Titanic PremiereJames Cameron’s Titanic is perhaps the essential ’90s film. Following its 1997 release, the disaster epic smashed records, winning 11 Oscars and generating well over $1 billion.
It also pushed its two leads into superstardom. In this photo, Kate Winslet and Leonardo DiCaprio can be seen turning heads at the 1998 Golden Globes.
Reese Witherspoon
When: 1999Where: Cruel Intentions premiereAs a young woman, Reese Witherspoon undoubtedly had quite the baby face. Here she is at the opening night of her movie Cruel Intentions, less than a month before 23rd birthday.
Dressed in a purple skirt and and white top, she certainly encapsulates the very best of ’90s red carpet fashion.
Jennifer Aniston
When: 1998Where: The Object of My Affection L.A. premiereLooking back, there were few individuals that defined the 1990s quite like Jennifer Aniston.
After finding fame as Rachel Green in Friends, it seemed that absolutely everyone wanted to emulate her style - most notably her hairdo. Always pictured looking her best, here she can be seen in 1998 at the opening night of movie The Object of My Affection.
Julia Roberts
When: 1997Where: Conspiracy Theory premiereJulia Roberts was another ’90s icon. Indeed, that was the decade in which she showed up in such hits as Pretty Woman, Hook, and Sleeping with the Enemy.
She even appeared in an episode Friends in 1996. But here, we see the star at the 1997 debut of the Richard Donner thriller Conspiracy Theory, in which she starred alongside Mel Gibson.
Kate Hudson
When: 2001Where: The Academy AwardsJust like a celebrity's first outing on the red carpet, The Academy Awards is the perfect time for a star to make their fashion mark. When Kate Hudson attended the 2001 ceremony, her dress wasn't met with much approval.
In 2014, though, the actress told the Evening Standard, “I was 21 years old when I was nominated for an Oscar for Almost Famous and to have Stella McCartney dressing me for the ceremony I felt like the hippest, coolest girl in the world. I woke up the next morning and turned on the television to find out I was on every worst-dressed list. So I called Stella, and we just laughed."
Geena Davis
When: 1992Where: The Academy AwardsGeena Davis was nominated for Thelma & Louise in 1992, but for the Oscars ceremony she wore a dress she probably wouldn’t even have been able to drive a car in. It was a short, ruffled affair created by Ruth Meyers and Bill Hargate.
Davis topped off the look with some long satin gloves and black tights. It was, if nothing else, very ’90s.
Céline Dion
When: 1999Where: The Academy AwardsCéline Dion stunned onlookers when she wore a Christian Dior tuxedo backward at the 1999 Academy Awards. Her song “The Prayer” from Quest for Camelot was nominated for an award, but it was the suit — specifically designed to be worn back-to-front — that drew attention.
Dion also wore diamond-encrusted Ray-Bans in exchange for a charitable donation from the company.
Cher
When: 1974Where: The Academy AwardsOver the years, Cher has made a habit of wearing weird, wacky outfits to the Oscars. For sheer daring, though, her 1974 ensemble takes the cake.
After all, that’s the year she wore a colorful sarong-like skirt and a bikini-like top designed by Bob Mackie. It’s a style that wouldn’t have looked out of place on a sunny beach somewhere.
Barbra Streisand
When: 1996Where: The Academy AwardsAfter the 1969 Academy Awards, there were two things everyone was talking about with regards to Barbra Streisand. Firstly, she tied for Best Actress with Katharine Hepburn.
Secondly, the actress and singer’s zany outfit — created by Arnold Scaasi — was somewhat...transparent. But to be fair to Streisand, she apparently had no idea just how see-through it would prove to be as the flashes fired and the camera shutters clicked.
Kim Basinger
When: 1990Where: The Academy AwardsBatman actress Kim Basinger tried something new and very unusual for the 1990 Oscars. In fact, she wore a white gown/tuxedo hybrid, complete with just one glove.
The star even designed it herself! And while many contemporary fashion critics scoffed at the look, the outfit is still talked about more than 30 years later. Clearly, Basinger had the last laugh.
Taraji P. Henson
When: 2018Where: The Academy AwardsEmpire star Taraji P. Henson rocked up to the 2018 Oscars wearing a black Vera Wang dress with a very daring slit and necklace.
But one month later the star told Entertainment Tonight that the gown could have been even more scandalous. She said, “I’m not afraid. Vera was like, ‘Let’s take it there!’ Wangy bangy, baby.”
Jennifer Lawrence
When: 2013Where: The Academy AwardsJennifer Lawrence wore a Dior Couture dress while accepting a Best Actress award at the 2013 Oscars. But it famously caused her a problem.
You see, the star fell over as she walked to the stage to collect her award for Silver Linings Playbook. Lawrence later revealed to British newspaper The Independent that dreams of cake meant that she had momentarily forgotten her stylist’s advice to kick the fabric away from her legs as she moved.
Gemma Chan
When: 2019Where: The Academy AwardsCrazy Rich Asians actress Gemma Chan chose an eye-catching Valentino gown for the 2019 Oscars. It was unique in many ways: it was large, it had a high collar, it was bright pink, and it had pockets.
Chan admitted later that she’d used the pockets to hide snacks to eat during the long ceremony.
Uma Thurman
When: 2004Where: The Academy AwardsFor the 2004 Academy Awards, Uma Thurman decided to wear a white lacy Christian Lacroix dress that billowed out as she walked. According to the subsequent press, the gown didn’t flatter her in the slightest.
The media actually dubbed the look “Swiss Miss,” and Thurman herself later expressed dissatisfaction with it. At least the look wasn't boring! Plus, it's impossible for Thurman to look bad in anything.
Penélope Cruz
When: 2007Where: The Academy AwardsPenélope Cruz dazzled audiences in 2007 when she showed up to the Academy Awards in a pink Atelier Versace dress with a feathered train. Everyone was impressed.
In fact, in February 2019 — over a decade after the fact — The Daily Telegraph declared that the gown was “everything and more than you could ever want from an Oscars dress.”
Charlize Theron
When: 2019Where: The Academy AwardsCharlize Theron had three things to show off at the 2019 Academy Awards: brown hair, shoulder blades, and a dress that complimented both. Theron’s chosen gown was a light blue design from the Haute Couture Christian Dior collection.
The stunning creation was wide open at the back and certainly got the job done.
Diane Keaton
When: 2004Where: The Academy AwardsDiane Keaton decided not to wear a dress at the 2004 Academy Awards and opted instead for a Ralph Lauren suit and bowler hat. Yet it wasn’t the first time that she’d done such a thing, as she’d worn a white suit in 1978 when the star won her Oscar for Annie Hall.
And while some loved the look, others felt differently. Either way, it was extremely memorable!
Lizzy Gardiner
When: 1995Where: The Academy AwardsCostume designer Lizzy Gardiner wished to feature a dress made out of American Express cards for The Adventures of Priscilla, Queen of the Desert, but the company wouldn’t let her. They did, however, let her wear said dress to the 1995 Oscars, where it gained plenty of attention.
In 1999, in fact, the gown was auctioned off, with the money going to an AIDS research foundation.
Cate Blanchett
When: 2016Where: The Academy AwardsCate Blanchett, nominated as Best Actress for Carol, rocked something both beautiful and unusual on the 2016 Oscars red carpet. Indeed, she wore a seafoam-green gown decorated with fabric flowers, a creation of Armani Privé.
Vanity Fair declared at the time, “Scientists have proven it is impossible to look at this dress and not gasp and then remain speechless for at least ten seconds.”
Marion Cotillard
When: 2008Where: The Academy AwardsIn 2008 Marion Cotillard channeled her inner mermaid and wore a beautiful Jean Paul Gaultier dress designed to look like fish scales. It turned out to be an extremely good night for Cotillard, too.
Not only did her gown win acclaim, but the star also picked up the Best Actress Oscar for playing Édith Piaf in La Vie en Rose.
Angelina Jolie
When: 2000Where: The Academy AwardsPeople might have mistaken Angelina Jolie for Morticia Addams when she picked up her Oscar for Girl, Interrupted in 2000. After all, the star wore a gothy black Versace gown and even had black hair extensions put in.
Yet it wasn’t the outfit that grabbed all the headlines, for that was the year Jolie kissed her brother on the Oscars red carpet.
Sharon Stone
When: 1998Where: The Academy AwardsSharon Stone decided to wear something a bit different for the 1998 Oscars. In fact, she paired an attractive lavender Vera Wang skirt with an ordinary white Gap shirt that belonged to her spouse, Phil Bronstein.
Fashion lovers everywhere were totally shocked, but the look went down in Academy Awards history.
Maya Rudolph
When: 2019Where: The Academy AwardsPink seemed to be the color of choice at the 2019 Academy Awards. Yet Bridemaids actress Maya Rudolph put a slightly different spin on things and wore pink florals instead with her Giambattista Valli gown.
Alas, Rudolph was slammed for the look on Twitter. The dress was, however, seriously on-trend at the time.
Cher
When: 1988Where: The Academy AwardsCher and her fashion collaborator Bob Mackie created a sheer black dress for the 1988 Academy Awards...a very sheer black dress. In fact, when Cher went up on stage to accept her Best Actress award for Moonstruck, the outfit left nothing to the imagination.
It was all completely outrageous — and made for an iconic Oscars moment.
Lupita Nyong’o
When: 2015Where: The Academy AwardsLupita Nyong’o wore a showstopper for the 2015 Oscars, in which she served as one of the presenters. The dress was a Calvin Klein creation featuring 6,000 white Akoya pearls, and it was worth at least $150,000.
It actually caught the attention of criminals, too. A week after the ceremony, in fact, the outfit was stolen from Nyong’o’s hotel room. Fortunately, though, the gown was located in the end.
Whoopi Goldberg
When: 1993Where: The Academy AwardsWhoopi Goldberg might just take home the award for the most colorful Oscars outfit of all time. Back in 1993, you see, Goldberg was hosting the ceremony and wore a purple satin coat that opened up to reveal a cascade of bright green.
Apparently, the actress had simply bought the dress in a boutique.
Nicole Kidman
When: 2007Where: The Academy AwardsNicole Kidman opted for a bright red Balenciaga dress when she attended the 2007 Academy Awards. The gown was striking enough on its own, but it also happened to have a massive train-like bow attached to it.
And while it met with rather mixed reviews at the time, the style is now considered one of Kidman’s best-ever looks.
Jayne Mansfield
When: 1956Where: The Academy AwardsThe fashion rules in 1956 were, of course, more conservative than they are now, but that didn’t stop Jayne Mansfield. That year, you see, the blonde bombshell posed in a daring dress in front of an Oscar statue with Cleo Moore.
The look created one of the most fabulous Academy Award photographs of all time.
Gwyneth Paltrow
When: 2002Where: The Academy AwardsWhen Gwyneth Paltrow arrived for the 2002 Oscars, people noticed that her sheer Alexander McQueen dress was maybe a little too sheer.
Paltrow thought so, too, and wrote on her website in 2013, “I still love the dress itself, but I should have worn a bra, and I should have just had simple beachy hair and less make-up.”
Michelle Williams
When: 2006Where: The Academy AwardsActress Michelle Williams attended the 2006 Academy Awards with her boyfriend Heath Ledger, with whom she’d had a baby daughter just three months previously. Her chosen yellow Vera Wang dress delivered – and then some – on the red carpet.
In fact, the gown was so acclaimed by the fashion industry that it even has its own Wikipedia page.
Kerry Washington
When: 2016Where: The Academy AwardsScandal star Kerry Washington wore a risqué Atelier Versace dress for the 2016 Oscars. And not only did it have a slit in the skirt up to her thigh, but it also included a leather bodice.
Elle magazine wrote at the time, “The hard-and-soft combo brings some necessary edge to the red carpet.”
Jennifer Lopez
When: 2012Where: The Academy AwardsJennifer Lopez arrived at the 2012 Academy Awards wearing a sparkling, silk Zuhair Murad gown decorated with crystal beads. It was beautiful — but the neckline may have been a little too low.
As she presented the Oscar for Best Costume Design, in fact, people thought they saw a wardrobe malfunction take place.
Charlize Theron
When: 2016Where: The Academy AwardsFor the 2016 Oscars, Charlize Theron wore a bright red Dior Haute Couture dress. She hadn’t actually seen it until two weeks before the event took place because she had been off filming in Germany.
But it’s probably safe to say that she was happy with it. After all, the plunging neckline showed off a 48.8-carat Harry Winston necklace.
Billy Porter
When: 2019Where: The Academy AwardsNot many men wear dresses on the red carpet, but Billy Porter is one who did. Yes, in 2019 he wore a spectacular Christian Siriano tux-gown to the Academy Awards.
He told Vogue magazine that same year, “We wanted to play between the masculine and the feminine. This look was interesting because it’s not drag. I’m not a drag queen; I’m a man in a dress.”
Angelina Jolie
When: 2012Where: The Academy AwardsAngelina Jolie wore a black Versace dress to the Oscars in 2012 and virtually created a whole movement. The sight of her leg sticking out of the elegant slit caused internet-fuelled chaos, in fact.
And before too long someone had set up a Twitter account devoted exclusively to Jolie’s leg – and it quickly gained 28,000 followers.
Shanina Shaik
When: 2019Where: The Academy AwardsModel Shanina Shaik wore a stunning Maison Yeya dress to a 2019 Oscars afterparty. She might not be wearing it again, though, because she suffered not one but two wardrobe malfunctions while walking the red carpet.
First, the strapless dress ended up being pulled down a little too far, and then the slit on her leg revealed her underwear. Oops!
Edy Williams
When: 1974Where: The Academy AwardsEdy Williams was one of the most scandalous actresses of her era. During the 1974 Academy Awards, for instance, she pulled off her fur coat to reveal nothing but a leopard-skin bikini underneath.
She would probably have shown the most skin of the whole ceremony if a streaker named Robert Opel hadn’t later run across the stage.
Lupita Nyong’o
When: 2014Where: The Academy AwardsThe year 2014 was a very good one for Lupita Nyong’o. After being nominated for her performance in 12 Years a Slave, the actress took to the Oscars red carpet in a blue Grecian-style Prada dress that established her as a fashion icon.
The gown was, she said, inspired by her hometown of Nairobi. Nyong’o also won the Best Supporting Actress award that night.
Mariah Carey
When: 2017Where: The Academy AwardsSinger Mariah Carey went to the 2017 Vanity Fair Oscars Party wearing a green chiffon dress created by Philipp Plein.
Some people raised eyebrows about the leopard print and dramatic cuts, but when Plein posted a picture of Carey in the dress on Instagram, everyone seemed to voice their approval.
Cate Blanchett
When: 2011Where: The Academy AwardsCate Blanchett’s dress for the 2011 Oscars won her lots of praise. It was a creation by Versace, and the actress utterly loved it.
As she told InStyle that April, “It was so architectural, and the breast piece is made all out of elastic. The color combination, I couldn’t believe it when I saw it in real life.”
Cindy Crawford
When: 1991Where: The Academy AwardsIn 1991 supermodel Cindy Crawford stepped out on the Oscars carpet, with Richard Gere on her arm, in a plunging red Versace dress. It became mega-famous, boosting the profiles of both Crawford and Gere.
And such was its influence that multiple copies were quickly produced. To this day, in fact, it regularly ranks highly in polls of the greatest dresses ever worn.
Björk
When: 2001Where: The Academy AwardsFamous musician Björk wore a curious creation at the 2001 Oscars ceremony: a gown that would become known as the “swan dress.” The dress was designed by Marjan Pejoski to look like a giant swan, and on her walk down the red carpet Björk dropped golden eggs.
It was all very weird – but it’s still remembered as an interesting piece of fashion history.
Halle Berry
When: 2002Where: The Academy AwardsHalle Berry’s dress at the 2002 Academy Awards became known as “the Elie Saab net dress,” so-called because of its mesh design. It was beautiful, form-fitting, and a massive success.
It’s even considered one of the best Oscar dresses ever made. Plus, Berry won Best Actress that night, becoming the first Black woman to do so.
Cher
When: 1986Where: The Academy AwardsAfter losing out on a Best Actress nomination for the 1986 Oscars, Cher decided to show up anyway and blow everybody away with a show-stopping outfit.
She asked Bob Mackie to create a black showgirl-style outfit with a massive headpiece, and the resulting dress immediately found a place in the annals of fashion history.