Top 50 Worst Oscar Dress Fails
“…and the Oscar goes to…” Every year the biggest names in the entertainment industry come together in Los Angeles to celebrate their talents and accomplishments over the past year at the glamorous Academy Awards, also known as the Oscars. While celebrities fret over nominations and speeches, millions of people around the world tune in to see their favorite actors and actresses, directors and producers, musicians, writers and crew members take home the coveted award.
Long before the awards, however, many fans tune in to watch their favorite celebrities take the red carpet in what has become an unofficial parade of fortune, fame and vanity. As reporters ask everything from “Who are you wearing?” to “Who is your date?”, stars lush over their designer gowns and dazzling jewels as they prepare for the night of the year. But, amid all of the dazzling smiles and witty comments, the fashion world is in a whirlwind as they dedicate hours of post-Oscar television to decide who was the best dressed and who was the worst.
Though everyone wants to look like a million bucks (which is easy to do as a celeb), the best-dressed celebrities at the Oscars are often the least memorable. Ask anyone who was the best-dressed at the 1996 Oscars and, more than likely, they will draw a blank! When it comes to the worst dressed, however, that’s an entirely different story! Join us as we roll out the red carpet and take a look at the top 50 worst Oscar dress fails of all time. Who will you recognize and remember? Let’s get started!
#50 – Kim Basinger
A household name in Hollywood in the 1980s, Kim Basinger made her acting debut on television in 1976 before taking her talents to the silver screen in the 1981 film Hard Country. Rising to prominence after playing a Bond girl in Never Say Never Again opposite Sean Connery, the award-winning actress has spent the last 30 years starring in films like 9 ½ Weeks, Batman, L.A. Confidential, 8 Mile and the upcoming, The Nice Guys.
Bringing an entirely new meaning to wacky and weird necklines, Basinger walked the red carpet at the 1990 Academy Awards in a shocking half-jacket gown that made absolutely no sense even then. The gown was decorated with gold embroidery but the coup de gras was the single satin glove that Basinger wore on her right arm in what appeared to be an homage to the King of Pop himself. Set to present Dead Poets Society as a nominee for Best Picture, Basinger may not have been nominated that evening but she undoubtedly took home the title of “Worst Dressed.”
#49 – Tyra Banks
One of the most recognizable models in the world, Tyra Banks began her career when she was 15 years old and rose to fame as the first African American woman to make the cover of the Sports Illustrated Swimsuit Issue and GQ magazine. Since then, the Victoria’s Secret Angel has established herself as a top-earning model with appearances on every magazine cover imaginable in addition to her work as an actress, host and talent judge on the popular America’s Next Top Model.
Standing at 5’10” tall with brown hair and hypnotic green eyes, Banks could seemingly look stunning in anything but that wasn’t exactly the case when she arrived at the 2000 Academy Awards in a bright purple ballerina gown. Though she wore it with confidence, Banks’ gown was a showstopper for all the wrong reasons with its strapless top and purple blush bottom that resembled a floor-length tutu or a throwback to the era of Southern belles. Come to think of it, maybe that’s where she was hiding her parasol, hand fan and gloves!
#48 – Heather Graham
Often ranked among the most beautiful and sexiest women in Hollywood, the 46-year-old Heather Graham is looking as gorgeous as ever after making her film debut nearly 30 years ago in License to Drive. Following up the film with her breakout performance in Drugstore Cowboy in 1989, Graham has continued to show off her surprising range as an A-list actress with starring roles in films like Boogie Nights, Austin Powers: The Spy Who Shagged Me and The Hangover.
Accustomed to wowing audiences with her beauty and keen sense of fashion, Graham’s 1999 venture down the red carpet at the Oscars wowed the world straight into shock. Invited to the event despite not being nominated or presenting, Graham arrived in a leather floor-length black dress with her hair pulled back in a half ponytail. And, although leather was trendy at the time, Graham looked better dressed for a Harley Davidson gala rather than a Hollywood star-studded event. The real question, however, is if she arrived by limo or on the back of a bike?
#47 – Barbra Streisand
Heralded as the “Queen of Divas,” Barbra Streisand is a living legend who is not only one of the best-selling music artists of all time but also the most decorated entertainer with two Academy Awards, five Emmys, 10 Grammys and 11 Golden Globes among dozens of others. First taking the stage in 1955, Streisand’s popularity as an artist and actress has stood the test of time over six decades with 33 top 10 albums and award-winning performances in films like Funny Girl, The Way We Were and A Star is Born.
Making her film debut in 1968 in Funny Girl, the following year was even bigger for Streisand when she was nominated for (and won) the Oscar for Best Actress. And, although she took home a huge victory, there was no chance she would take home any awards for her outfit after she took the stage in a transparent pantsuit covered in sequins. Resembling something straight from a figure skater’s wardrobe, Streisand’s Oscar debut was definitely memorable but it wouldn’t be the last time the diva turned heads for her sense of style (or lack thereof).
#46 – Cameron Diaz
From a 16-year-old fashion model featured on the cover of Seventeen magazine to a young actress starring in independent films, the 43-year-old Cameron Diaz has come quite a long way from her early days in Hollywood. Rising to fame with films like The Mask and There’s Something About Mary in the late 1990s, Diaz is now one of the highest paid actresses over 40 whose performances in films like Being John Malkovich, Shrek and Vanilla Sky have earned her widespread praise and lasting critical acclaim.
Invited to the 2002 Academy Awards to present the award for Best Art Direction (everyone’s favorite category, of course), Diaz made a bold choice with a full-bodied floral print gown designed by Emanuel Ungaro. An eclectic mix between Asian-inspired and a bohemian bathrobe, Diaz paired the pink and red atrocity with a bulky turquoise bangle and a purple Indian necklace that doubled as a belt. Claiming she wanted something casual, Diaz told People magazine, “I feel like I just got out of bed and threw it on.” Unfortunately for her, it looked that way too.
#45 – Melanie Griffith
Though perhaps less popular on the silver screen today than in decades past, the 58-year-old Melanie Griffith has already had a lifetime’s worth of success since making her acting debut in the 1970s opposite Gene Hackman in Night Moves. From there, the award-winning actress has starred in dozens of films and television series such as Body Double, Something Wild, Working Girl and Hawaii Five-O in addition to making her Broadway debut in the revival of Chicago.
Nominated for an Academy Award for Working Girl in 1988, Griffith was already an Oscar veteran by the time she took the red carpet again in 2005 with her husband, Antonio Banderas, as he prepared to perform a number from The Motorcycle Diaries. Unfortunately, while her husband looked hotter than ever, Griffith seemed like she had a motorcycle story of her own when she arrived hobbling on a broken foot and using a cane. To top it off, her Atelier Versace gown was a huge disappointment that washed out her pale complexion, barely hid her cast and left many wondering where her matching top hat was hidden!
#44 – Meryl Streep
No stranger to the Academy Awards (or any other award for that matter), Meryl Streep has been nominated for an incredible 19 Oscars, more than any other actor or actress in the history of film. Earning her first award nomination in 1979 for The Deer Hunter, the 66-year-old’s first Oscar win came in 1980 with the film Kramer and Kramer, which she followed up in 1983 with another win for Sophie’s Choice. She’s since been nominated for her work in dozens of films including The Devil Wears Prada, Julie & Julia and Into the Woods.
Invited to present the Honorary Academy Awards segment and also nominated for Best Actress for her portrayal of Margaret Thatcher in The Iron Lady, Streep arrived at the 2012 Oscars looking like an Oscar herself. Dressed from head to toe in gold, Streep’s flowing gown wrapped around her curvy figure and gathered at her waist creating a less than flattering silhouette. Luckily enough, Streep’s gown was the only disaster of the evening after she won the Oscar for Best Actress and posed with her lookalike, the Oscar statue himself, after the ceremony.
#43 – Berenice Bejo
Perhaps a relatively unknown name for anyone who doesn’t enjoy foreign or silent films, the stunning Berenice Bejo is a French Argentinian actress who made her American acting debut opposite Heath Ledger in the 2001 film, A Knight’s Tale. Now 39 years old and well established as an incredibly talented foreign film actress, Bejo’s most recent and award-winning role comes from her performance as Peppy Miller in the 2011 silent film, The Artist.
Despite her gorgeous and exotic beauty, Bejo proved in 2012 that redheads (natural or not) shouldn’t wear mint-colored gowns regardless of the occasion. Bejo was nominated for Best Supporting Actress for The Artist but went home empty-handed aside from a truckload of comments that criticized her Elie Saab gown and her vibrant red locks. While the gown itself was stunning and by far from the worst (remember Meryl Streep’s Oscar lookalike?), it was enough to send fashion critics over the edge and leave this French star questioning her wardrobe choice! Maybe next time!
#42 – Kate Mara
Born into the legendary family who owns the New York Giants of the NFL, Kata Mara paved her own way to stardom after making her television debut in 1997 on Law & Order. She continued to star in minor roles throughout the early 2000s before her 2005 performance in Brokeback Mountain made her a household name. Now known for her roles in series like House of Cards and 24 as well as in films like We Are Marshall, The Martian and Fantastic Four, Mara is definitely climbing her way to the top of Hollywood’s finest!
Nominated for Best Actress for her role in The Girl with the Dragon Tattoo, Mara arrived at the 2012 Oscars looking a bit uncomfortable, awkward and out of place in a blush-colored Elie Saab dress (that makes two in a row for those counting!). Far from flattering, the gown was a catastrophe with its delicate sleeve that dangled at the elbow leaving her right arm useless for anything other than a shy wave. The floral and lace overlays did little to help and left this typically stunning beauty appear as though she was dressed in an oversized doily from her grandmother’s closet!
#41 – Anna Paquin
Seemingly in front of the camera for decades now, it’s hard to believe that Canadian actress Anna Paquin is only 33 years old. In a stroke of luck as a child with high hopes of becoming a star, the 10-year-old Paquin beat out 5,000 other candidates for the role of Flora McGrath in the 1993 film The Piano. Despite having very little acting experience or training, the young Paquin gave the performance of a lifetime and was nominated for Best Supporting Actress at the 1993 Academy Awards.
Taking home the Oscar and becoming the second youngest Academy Award winner in history, not even Paquin could escape the crime of children’s fashion in the early 1990s. Making her way down the red carpet in a blue dress, boots and a hat, Paquin’s ensemble looked like a cross between a Lisa Frank design and a life-size American Girl doll. We just don’t know what’s worse – knowing someone picked the outfit for her or realizing she’ll never live down the Smurf Dress Catastrophe of 1993.
#40 – Jodie Foster
Often considered one of the best actresses of her generation, Jodie Foster made her acting debut at five years old on Mayberry R.F.D. before her breakout performance in Martin Scorsese’s 1976 blockbuster, Taxi Driver, put her name on the map. Now at 53 years old and with over four decades in the spotlight, the award-winning actress is known for her critically acclaimed performances in iconic films like Silence of the Lambs and Nell.
The 1989 Academy Awards was a game changer for Foster who was nominated for Best Actress for her role as Sarah Tobias in The Accused. The young star won the award over other Hollywood veterans like Meryl Streep and Melanie Griffith while turning heads for her iconic 1990s Alice in Wonderland cocktail gown. Stopping at the knees and featuring a ruffled train, Foster’s look was – to use a phrase from Alice herself – “entirely bonkers” especially with her white pantyhose and black high heels. Now that’s a fashion faux pas we can’t forget!
#39 – Hilary Swank
Making her film debut in Buffy the Vampire Slayer in 1992, Nebraska native Hillary Swank landed the role of a lifetime two years later when she was cast as the lead in The Next Karate Kid. Now at 41 years old and busier than ever, Swank is a two-time Academy Award winner whose talent has taken the world by surprise with her exceptional performance in popular films like Boys Don’t Cry and Million Dollar Baby.
Invited to the 2003 Academy Awards to present The Hours as a nominee for Best Picture, Swank sadly joined the ranks of prom dress victims. Designed by Dior, the gown featured a light pink bodice that stopped mid-thigh but went horribly wrong with a tulle overlay that faded from light to dark pink. Resembling a cross between a ballerina and an upside down strawberry parfait, Swank’s red carpet walk was shockingly delicate for someone preparing to make her debut in the boxing ring with Clint Eastwood himself.
#38 – Jennifer Lopez
Still as gorgeous as ever at 46 years old, everything Jennifer Lopez does seems to be golden. First getting her start as a backup dancer for New Kids on the Block in the early 1990s, Lopez has become a cultural icon and one of the most influential Hispanic entertainers of all time. But, it doesn’t stop there as the New York native has extended her reach from dancing, singing and acting to mentoring young artists on the popular talent competition, American Idol.
Though Lopez has never been nominated for an Oscar, she’s been to the Academy Awards plenty of times and, along with worst-dressed nominee Cameron Diaz, presented Best Costume Design and Best Makeup at the 2012 awards. In fact, Lopez could’ve used a costume designer herself that year after she emerged from the limo onto the red carpet in a clamshell dress. Designed by Zuhair Murad, the drastic v-cut in the front and back did little to help the gown’s distracting lines that left everyone dizzy and entranced by Lopez’s famous curves and voluptuous derriere.
#37 – Anne-Sophie Bion
Much like Berenice Bejo, Anne-Sophie Bonn may not be a well-known name in the United States but she is already an Academy Award nominated film editor. Born in France, Bonn has something else in common with Bejo in that she is best recognized for her work behind the scenes on the award-winning 2011 silent film, The Artist. Since then, Bion has continued to prove her talents working on films such as War of the Buttons, Stars 80 and Chinese Puzzle.
Shortly before Jennifer Lopez walked the red carpet at the 2012 Academy Awards in her clamshell gown, Bion led the way in a black floor-length dress that unsurprisingly created a buzz. Bion was nominated for Best Editing for The Artist and, though she went home empty-handed, she was definitely the topic of conversation after wearing what resembled an oversized garbage bag with holes cut out for her arms and neck. Though France might be fashion forward, this was definitely a hard lesson for the rising star to learn in what’s hot and what’s not in Hollywood.
#36 – Diane Keaton
Spending nearly 50 years winning the hearts of audiences with her incredible talent, the 70-year-old Diane Keaton made her film debut in 1972 in The Godfather. Catching the eye of director Woody Allen, the two teamed up in films like Sleeper, Annie Hall and Play It Again, Sam that took Keaton to an even greater level of fame. From there, she established herself in a variety of genres and earned critical acclaim for her performances in films like Reds, Marvin’s Room and Looking for Mr. Goodbar.
Starring in Something’s Gotta Give in 2003 and once again met with outstanding praise, Keaton was nominated for Best Actress at the 2004 Oscars but lost out to Charlize Theron (who we’ll see later on the list). Although we may be cheating here, we couldn’t help but include Keaton’s 2004 ensemble – a suit designed by Ralph Lauren and intended to resemble her character from the 1977 film Annie Hall. Apparently neither her suit nor her character aged well since the fashion police called Keaton’s look a tragedy from head to toe!
#35 – James Franco
Eccentric doesn’t even begin to adequately describe the 38-year-old James Franco. Launching his career on the short-lived cult series Freaks and Geeks, Franco truly became a star after his award-winning performance in the 2001 television film James Dean. He then went on to star in critically acclaimed films like 127 Hours while showing his lighter side with comedic romps in This is the End, Pineapple Express and The Interview before taking the stage in 2014 for his Broadway debut in Of Mice and Men.
In 2011, Franco was asked to host the Academy Awards alongside Anne Hathaway in a decision that was later heavily criticized. While Diane Keaton paraded down the red carpet in a suit, Franco actually dressed as Marilyn Monroe while Hathaway donned a tux in what was intended to be a jab at Hugh Jackman’s inability to sing. Though awkwardly funny at the time, Franco is definitely not a man who can pull off drag even with help from some of the best makeup artists in Hollywood.
#34 – Kate Winslet
The youngest person to ever receive six Academy Award nominations (with seven total in her career so far), Kate Winslet became a Hollywood star in her early 20s after an astounding performance in Titanic opposite Leonardo DiCaprio. A force to be reckoned with on the silver screen, the 40-year-old Winslet has earned international fame after starring in hit films such as Eternal Sunshine of the Spotless Mind, Finding Neverland, The Holiday and Steve Jobs.
Before the 1997 release of Titanic truly made her an A-list actress, Winslet attended the 1996 Academy Awards as a nominee for Best Supporting Actress in Sense and Sensibility but lost the Oscar to Mira Sorvino. An obvious newcomer to Hollywood at the time and naïve to the fact that pink was a fashion faux pas on the red carpet, Winslet arrived in a pink gown and faced some of the harshest criticism of the night with many saying that she looked like a walking bottle of Pepto-Bismol! Now that had to sting a little!
#33 – Sarah Jessica Parker
Making her film debut in 1980s flicks like Girls Just Wanna Have Fun and Footloose, Sarah Jessica Parker established herself as a fashion icon thanks to her leading role as Carrie Bradshaw on the hit HBO series Sex and the City. Parker spent six years on the show, won two Emmy Awards and worked as an executive producer before realizing just how far she had come since making her Broadway debut in 1976 at only 11 years old.
Someone call the fashion police, it’s an emergency! Parker took the stage at the 2010 Academy Awards with Tom Ford to present the award for Best Costume Design but, ironically enough, she could have easily used some design help herself. Falling off the fashion bandwagon wearing an asymmetrical Chanel dress, Parker’s wardrobe choice left many distracted and wondering, “Is it green or is it yellow?” Though it failed to flatter her petite frame, the dress did have some stopping power since it ended mid-thigh and showed off her killer legs!
#32 – Jennifer Hudson
Taking the stage on the third season of American Idol (and placing seventh), the world knew that Jennifer Hudson would have an incredible career as a singer but no one ever imagined she had the acting chops to go with it. The Grammy Award winning artist made her film debut in the 2006 film Dreamgirls and has since appeared in hits such as Sex and the City, The Secret Life of Bees and Winnie Mandela.
Literally everywhere from walking the red carpet to three performances with Beyonce on the stage, Hudson was all over the place at the 2007 Academy Awards where she was nominated for and won the Oscar for Best Supporting Actress. Though her brown Oscar de la Renta dress was less than stellar, the real fashion crime that had everyone talking was the snakeskin short blazer that she wore before the show. Clashing with the gown, the blazer ruined her classic look that left many breathing a sigh of relief when she ditched it before taking the stage.
#31 – Melissa McCarthy
Easily one of the most popular comedic actresses in the industry today, Melissa McCarthy got an early taste of fame on hit television series like Gilmore Girls and Samantha Who? in the early 2000s. Over the past few years, the 45-year-old McCarthy has become one of Hollywood’s favorite leading ladies thanks to memorable performances in television sitcoms like Mike and Molly as well as in films including Identity Thief, The Heat, Spy and the upcoming Ghostbusters reboot.
Obviously a year of Oscar dress fails, the 2012 Academy Awards took another victim after McCarthy and the Bridesmaids cast presented a total of three awards with McCarthy nominated for Best Supporting Actress (which she lost to Octavia Spencer). Dressed in a Marina Rinaldi gown, McCarthy didn’t exactly look her best with the gown’s high neckline and beaded waist that made her look short and frumpy. Though the gown’s champagne hue flattered her hair color and complexion, the design itself was lacking especially for such a beloved Hollywood star.
#30 – Jennifer Lopez
Making her second appearance on our list, Jennifer Lopez experienced a series of career setbacks in 2009 after her seventh studio album, Love?, failed to produce a chart-topping single and led her to part ways with Epic Records. By 2010, Lopez had big plans to rejuvenate her career and used her invitation to the Academy Awards to do exactly that and regain her place in the spotlight – or so she hoped.
Invited to present the Oscar for Best Original Score alongside Sam Worthington, Lopez was definitely the topic of conversation but it wasn’t the way she intended. A far cry from her clamshell dress from earlier on the list, Lopez’s 2010 venture down the red carpet was even worse with an off-white Armani gown that was modest in comparison but far more atrocious. Resembling a hybrid of fish scales and bubble wrap, the gown hugged most of her famous curves until its extra material gathered on her left hip leaving many to wonder if she needed an extra chair for her bulky sidekick!
#29 – Nicole Kidman
Breathtakingly beautiful and incredibly talented, Australia’s Nicole Kidman has become one of the most respected actresses in Hollywood since her breakout performance in the 1989 thriller Dead Calm. Since then, the 48-year-old award-winning actress has starred in a wide variety of films including Moulin Rouge, The Hours and To Die For not to mention making dozens of headlines for her high profile marriages to Tom Cruise from 1990 to 2001 and Keith Urban, whom she married in 2006.
Following in Jennifer Lopez’s footsteps from 2010, Kidman presented the 2011 Academy Award for Best Original Score with Hugh Jackman. Also nominated for Best Actress for her performance in Rabbit Hole (which she lost to Natalie Portman), it was a huge night for Kidman who faced mixed reviews from fashion critics when she walked the red carpet in a Dior gown accentuated with silver flourishes. While many argued that the dress cinched her waist and broadened her hips, we couldn’t help but notice her orange stilettos that, without a doubt, made the outfit!
#28 – Sacha Baron Cohen
If James Franco is eclectic, then Sacha Baron Cohen is the epitome of unpredictable. Hailing from London and first working as a model, Cohen made his film debut in the late 1990s but found fame as an internet sensation thanks to a series of Lee Jeans commercials where he played Super Greg. Now known for characters like Ali G, Borat, Bruno and Admiral General Aladeen, Cohen is considered one of the funniest and most talented actors in Hollywood.
Already well established in 2012 as a talented, award-winning and unpredictable comedian, Cohen made a huge splash at the 2012 Academy Awards but not because he was nominated for or presenting an award. Instead, he arrived in full military garb to promote his latest film, The Dictator. In character from head to toe, Cohen escorted two beautiful women (who were also in military garb) down the red carpet causing everyone to stop and stare. After all, wasn’t that the point?
#27 – Jennifer Connelly
Launching her career as a child model, New York native Jennifer Connelly became a well-known name in Hollywood after appearing in films like Labyrinth and The Rocketeer in the late 1980s and early 1990s. Continuing to expand her talents while growing up in front of the camera, the 45-year-old Connelly has earned critical acclaim after landing more dramatic roles in blockbuster hits such as Requiem for a Dream, House of Sand and Fog, A Beautiful Mind, Hulk and Noah.
With A Beautiful Mind nominated for several awards at the 2002 Academy Awards, Connelly was one of four wins of the evening when she took home the Oscar for Best Supporting Actress. Her gown, however, was an entirely different story and was a far cry from being Oscar worthy. Designed by Nicolas Ghesquiere, the khaki colored dress featured a simple strapless top but told a rags to riches story with its bohemian layered skirt. Finished with a scarf that resembled an ace bandage or a dirty towel, this gown definitely choked on the red carpet!
#26 – Madonna
Better known as the “Queen of Pop,” Madonna is one of the most popular names in music today thanks to a career that spans nearly four decades and over 300 million records sold worldwide. Bursting onto the music scene in the 1980s with hits like “Vogue,” “Like a Virgin” and “Papa Don’t Preach,” the Michigan native has even taken her talents to film where she’s proven herself as an award-winning actress in flicks like Dick Tracy, Evita and A League of Their Own.
Living up to her reputation of having an eccentric and free-spirited personality, Madonna made yet another bold and risqué fashion choice at the 2010 Oscars when she arrived in an outfit that could have easily won the “Worst Dressed” or “Strangest” award. Inspired and made by her personal designer Francesco Scognamiglio, Madonna’s see-through outfit included a Spanx-style bodice, a fur vest and fishnet stockings that left little to the imagination. Luckily, Madonna didn’t perform or present which kept her fairly safe from flashing the crowd with her barely-there ensemble.
#25 – Madonna
Much like Heather Graham from earlier on our list, Madonna was invited to the 1999 Academy Awards without being nominated for or asked to present an Oscar. As a matter of fact, Madonna was at a low point in her career and hadn’t appeared in a film for over three years. Despite this, the Queen of Pop took the red carpet and proved her unique style once again in a dress choice that left many wondering, “What was she thinking?”
With the growing popularity of Asian culture thanks to films like Crouching Tiger Hidden Dragon and Memoirs of Geisha in the late 1990s, Madonna’s two-piece outfit paid homage to the growing trend but didn’t quite go over as planned. Having already set the bar high with her iconic pointy bra, the Asian ensemble was a huge fashion flop for the music icon whose red hair and pale complexion left her looking stylistically confused. Lucky for us, the Queen of Pop bounced back in the new millennium!
#24 – Geena Davis
Tall and gorgeous, it’s no surprise that Geena Davis was working as a model when she was cast by Sydney Pollack to star in his 1982 film Tootsie. Moving to soap operas and television series such as Family Ties and Remington Steele, Davis earned critical acclaim for her 1988 performance in The Accidental Tourist. Since then, she has had award-winning roles in everything from comedies and monster movies to sports flicks and dramas like Beetlejuice, The Fly, A League of Their Own and Thelma & Louise.
The 1992 Academy Awards was a huge event for Davis who presented the Oscar for Best Film Editing alongside her Thelma & Louise costar Susan Sarandon. With both nominated for Best Actress (which went to Jodie Foster), the worst part of the evening wasn’t losing the Oscar. Instead, Davis took the stage in a dress that made her look like a bride straight out of a Madonna music video. Designed by Ruth Meyers and Bill Hargate, the corset-style bodice definitely accentuated Davis’s bouncing chest but, between the black pantyhose and the train, this gown is one that definitely hasn’t aged well.
#23 – Taraji P. Henson
Better known today for her role on the smash hit television series Empire that has earned her a Golden Globe Award and an Emmy nomination, Tarji P. Henson has been around Hollywood for over two decades after first launching her career on television in 1995. Making her silver screen debut in the 2001 film Baby Boy, Henson has starred in several television series and films including The Curious Case of Benjamin Button, Date Night, The Karate Kid (remake), Boston Legal and Eli Stone.
Still somewhat of a newcomer to Hollywood in 2006, Henson was invited to the Academy Awards to perform “It’s Hard Out Here for a Pimp” with Three 6 Mafia from the film Hustle and Flow (which won Best Original Song). Taking the stage in a flowing electric blue gown complete with a train, Henson showed off her every curve with the form-fitting design that featured jeweled straps that barely kept the top of her gown in place. Though not our favorite look on the star, there’s no doubt that Henson was grateful for fashion tape to keep everything in place during her big night.
#22 – Barbra Streisand
Making her second appearance on our list as the director and star of the 1991 romantic drama The Prince of Tides, Barbra Streisand expected great success with her movie after it was nominated for seven Academy Awards including Best Picture. The Academy had other plans, however, after the film lost to Silence of the Lambs making the 1992 Oscars a complete flop for Streisand whose horrific gown might have set the tone for the evening from the moment she walked the red carpet.
Despite being considered one of the most elegant artists and actresses of all time, Streisand’s ensemble at the 1992 Oscars was anything but fashionable. Resembling a costume taken from someone’s trunk in the attic, Streisand’s mauve gown ignited a series of flying squirrel jokes likely heard ‘round the world. And, to make matters worse, the star crimped her hair leaving many to wonder if she got dressed in the dark or was hoping to transform into a modern-day Egyptian queen! Whatever the case, we’re glad it’s over!
#21 – Uma Thurman
One of the most versatile actresses to take the stage over the last 20 years, Uma Thurman first rose to fame in 1994 with her Oscar-nominated performance in Pulp Fiction. Spending the early 1990s starring in films like Batman & Robin, The Truth About Cats & Dogs and Les Miserables, Thurman found even greater fame in the early 2000s with the Kill Bill series in addition to working on television hits such as Hysterical Blindness and Smash.
Invited to present the Oscar for Best Cinematography to Master and Commander: The Far Side of the World alongside Jude Law at the 2004 Academy Awards, Thurman embraced her Swiss heritage with a dress that left everyone stunned. Easily mistaken for a pirate’s bride, Thurman looked like she belonged on a hot chocolate package rather than the red carpet thanks to the dress’s billowing sleeves, odd cuts and unflattering belt. Giving her an A+ for effort, there might’ve been a better venue to rock this look – a Halloween party or a yodeling contest – but definitely not the Oscars!
#20 – Susan Sarandon
Launching her acting career in the 1970s, New York native Susan Sarandon became a household name in Hollywood thanks to her breakout role in the 1975 cult classic The Rocky Horror Picture Show. Since then, the 69-year-old Academy Award winner has been nominated for a flurry of awards thanks to her legendary work in film, television and on the stage in hits like Atlantic City, Thelma & Louise, The Client and Bull Durham as well as the Broadway revival of Exit the King.
Undoubtedly enjoying many high points throughout her career, Sarandon was nominated for Best Actress in 1996 for her stellar performance in Dead Man Walking. Long before accepting the award, however, Sarandon left audiences speechless when she walked the red carpet in this gold Dolce & Gabbana gown that was simply too much even for the 1990s. As for the sunglasses, she could’ve at least passed a few extra pairs around as this fashion faux pas is so ugly it’s blinding!
#19 – Selma Blair
Leaving Michigan and moving to New York at just 20 years old to pursue a career in acting, Selma Blair landed her first professional role three years later in 1995 on an episode of Nickelodeon’s The Adventures of Pete & Pete. She then made small appearances in television and film before becoming an overnight sensation thanks to her role in the 1999 teen drama Cruel Intentions. Since then, she’s appeared in films like Hellboy and The Sweetest Thing while recently making headlines after her portrayal of Kris Jenner in the miniseries, The People v. O.J. Simpson.
Rising to international stardom at the dawn of the new millennium, Blair was obviously too busy working and missed the memo about tassels being in style. Making her appearance at the 2002 Oscars, Blair’s tasseled red gown proved to be a hot topic of hide and seek that left many people wondering, “What was she thinking?” Looking more like a cross between a 1920s flapper gown, a swimsuit or an ice skater’s costume, Blair could’ve found a more flattering way to show off her sexy and svelte figure!
#18 – Tilda Swinton
Hailing from London, Katherine Matilda “Tilda” Swinton is one of the most respected actresses in the industry. First joining the Royal Shakespeare Company in 1984, Swinton has spent the majority of her career avoiding mainstream roles and has, instead, become an arthouse darling. Now at 55 years old, the Academy Award winner has continued to prove her talents with numerous awards for her work in films like The Deep End, Michael Clayton, The Grand Budapest Hotel and Trainwreck.
Towering at 5’11” and easily one of the tallest actresses in the industry, the redheaded Swinton is also known for her androgynous and unique style, although she might have taken things a bit too far in 2008. Making the “Worst Dressed” list for the evening, Swinton wore a black Lanvin gown that resembled an oversized trash bag or a pool table cover dusted off from a deserted and decrepit biker bar. Lucky for Swinton, “Worst Dressed” wasn’t the only title she took home that night after winning an Oscar for Best Supporting Actress in Michael Clayton.
#17 – Juliette Binoche
While not many young American moviegoers will recognize Juliette Binoche, the French actress, dancer and artist has been in Hollywood for over 30 years. Born into an artistic family, Binoche took acting lessons as a child and quickly flourished as a star in France before making her English debut in The Unbearable Lightness of Being in 1988. Catching Steven Spielberg’s eye but declining multiple offers to star in his hit film Jurassic Park, Binoche went on to gain American fame after her stellar performances in The English Patient and Chocolat.
On the heels of the critically acclaimed release of The English Patient in 1996, Binoche walked the red carpet at the 1997 Oscars wearing a velvet copper gown designed by Sophie Sitbon. Resembling something that a villain from Flash Gordon might wear, the dress was far too much for Binoche’s petite frame with its Dracula collar as the icing on the cake for everything that could possibly go wrong with one dress. There was, however, a silver lining for the French star who took home Best Supporting Actress for the film only to win again in 2001 for Chocolat.
#16 – Demi Moore
Taking the world by storm in the 1980s as a member of the Brat Pack alongside stars like Emilio Estevez, Rob Lowe and Molly Ringwald, Demi Moore caught her first major break in 1985 after starring in St. Elmo’s Fire. A year later, the New Mexico native became a real Hollywood star after earning widespread praise for About Last Night. Now at 53 years old, Moore is still one of the biggest names and hottest stars in the industry known for her work in films like Ghost, A Few Good Men, Indecent Proposal, G.I. Jane and many more.
Long before Moore ever made headlines with Ashton Kutcher, she walked the red carpet with her second husband and Hollywood legend, Bruce Willis. In 1989, Moore planned on becoming an even bigger star only this time in the fashion industry when she designed her own dress for the Oscars. Using bicycle shorts, lace trim, a lingerie bodice and a wild pattern, Moore’s look was the talk of the event with her gown resembling a Halloween costume fit for a Hollywood fright-night queen. Thankfully, she’s learned her lesson and now leaves designing gowns up to the experts.
#15 – Gwyneth Paltrow
Making her acting debut at just 17 years old, Gwyneth Paltrow has done just about everything imaginable in Hollywood as an award-winning actress, model, singer and food writer. The 43-year-old has worn fat suits to get laughs, appeared in a Johnny Depp cash grab, dated Ben Affleck and Brad Pitt, and is currently on the superhero kick alongside Robert Downey Jr. in the Marvel franchise. Add in films like Shakespeare in Love, Emma and Proof, and it’s no surprise why she’s one of Hollywood’s favorite leading ladies.
Widely criticized in the late 1990s for walking the red carpet in an all-pink gown that looked like it was fit for a high school prom and a bubblegum award, Paltrow went to the extreme opposite for her look at the 2002 Oscars. Definitely a far cry from a pink princess, Paltrow wore an Alexander McQueen gown that featured a sheer tank top and a flowing skirt that, when paired with dark eyeliner and her pale complexion, left Paltrow looking more like a glamourous goth than a silver screen star.
#14 – Cher
Known as the Goddess of Pop, Cher will celebrate her 70th birthday in May not to mention her career as a singer, actress and model that spans over 50 years. First gaining popularity in the 1960s alongside her husband as Sonny & Cher and known for their hit single “I Got You Babe,” Cher went on to become a superstar as she proved her talents on Broadway and on the silver screen with award-winning performances in hits like Silkwood, Mask and Moonstruck before reviving her music career once again.
No stranger to making headlines for her sense of style, Cher’s over-the-top outfits at the Oscars became a norm after 1986 when she left everyone speechless and for good reason! Walking the red carpet like a hybrid between a Las Vegas showgirl and a futuristic space villain or Xanadu thing, Cher actually intended to make a “statement” with this Bob Mackie design since she didn’t earn a nomination for her performance in the 1985 film Mask. Whatever the statement was, this dress was undoubtedly a conversation piece and a showstopper!
#13 – Cher
Not again! Obviously with more to say after her gown at the 1986 Oscars, Cher returned to the red carpet in 1988 when she was nominated for Best Actress for her performance in Moonstruck. Arriving to the awards in yet another Bob Mackie design, Cher’s 1988 gown made less of a statement and, instead, attracted a lot of eyes as it left little to the imagination with its sheer and bejeweled fabric that hugged the star’s every curve.
Walking like an Egyptian (or maybe only resembling one), Cher was 42-years-old when she shocked the media by proudly baring it all for her fans, colleagues and the rest of Hollywood. She even received the ultimate vindication from her 1986 Oscar loss when she beat out Glenn Close, Holly Hunter, Sally Kirkland and the legendary Meryl Streep to take home the Best Actress award for the night. We can only imagine what her outfit looked like center stage under all of those bright Hollywood lights!
#12 – Faith Hill
Rainbow sherbert, anyone? Mississippi native Faith Hill might have recently been replaced on the Sunday Night Football intro by Carrie Underwood, but she’ll always be country music’s favorite blonde bombshell of the 1990s. Making waves with her Take Me as I Am debut album in 1993, Hill earned major success with her follow up albums – Faith and Breathe – that featured hits like “This Kiss,” “The Way You Love Me” and “Just Breathe.” If being an award-winning artist wasn’t enough, Hill is also half of one of Nashville’s hottest couples as the wife of country music heartthrob Tim McGraw.
Invited to the 2002 Oscars to sing “Somewhere Over the Rainbow” from The Wizard of Oz in a tribute to some of the greatest songs in film history, Hill took the invitation and performance to heart when she picked out her gown. Though it’s nearly impossible to imagine Hill looking bad in anything, this Versace gown just might do the trick. Designed to look like a rainbow, the gown made Hill’s bottom half look like a swirl of rainbow sherbert or a melting popsicle in the heat of summer. Either way, we definitely couldn’t find the lucky charm in this dress fail!
#11 – Celine Dion
Once of the best-selling artists of all time and one of the most famous female singers to ever walk the earth, Celine Dion has come a long way from her hometown of Charlemagne, Quebec where she emerged as a teen star. Becoming an international sensation by the 1980s, Dion’s award-winning career has helped establish her as one of the richest people in music history with her most recent stint at Caesar’s Palace in Las Vegas where she’s known for her outstanding five-star show.
Winning Best Original Song in 1998 for “My Heart Will Go On” in one of the most memorable films in history – Titanic, Dion was invited back to the Oscars in 1999. Always an icon of fashion, Dion opted to follow the latest trend and wore a pantsuit to the event. The star’s all-white suit not only hid her petite frame with its oversized and baggy cut, it left many confused as she appeared to have the jacket on backward. Though we’re still not quite sure what she was thinking, we’re glad to see Dion is now back to her elegant ways and prettier than ever before!
#10 – Anna Nicole Smith
Instantly famous after being named the 1993 Playboy Playmate of the Year, Anna Nicole Smith found herself permanently in the spotlight but not for landing modeling contracts with companies like Guess, H&M and Lane Bryant. Instead, Smith made headlines for her highly publicized marriage to an octogenarian oil tycoon who was on his deathbed. With his passing in 1995 and the confusion regarding his estate, Smith reemerged in the new millennium as a reality television star before her tragic death in 2007 from a drug overdose.
With no chance of ever earning an Academy Award, Smith was still invited to the 1996 Oscars and took her red carpet walk as a chance to shine – or so she thought. Arriving at the event looking out of sorts and much heavier than before, Smith wore a turquoise velour gown with a slit all the way up her thigh. Regardless of her size, Smith’s dress was a huge fashion fail that left her looking like a trailer park version of Betty Rubble from The Flintstones with a bejeweled broach resembling Barney Fife’s coveted sheriff’s star!
#9 – Kate Hudson
With legendary Hollywood actress Goldie Hawn as her mother, it’s no surprise that Kate Hudson has already made a name for herself at only 36 years old. Earning a Golden Globe for her breakout performance as Penny Lane in the 2000 hit Almost Famous, Hudson quickly became the go-to star for romantic comedies with hits like How to Lose a Guy in 10 Days, Raising Helen, Bride Wars and You, Me and Dupree.
Easily one of the hottest stars in Hollywood, Hudson attended the 2001 Oscars with the hopes of taking home the Best Supporting Actress award for Almost Famous in addition to her Golden Globe. Unfortunately, Hudson didn’t make the cut and instead took home a handful of “Worst Dressed” awards for her grey semi-sheer Stella McCartney gown with fringe shoulders and a high collar. While the dress itself was bad enough, Hudson’s curly hair was the cherry on top that made her look like a Victorian socialite instead of a rising Hollywood star!
#8 – Diablo Cody
After spending a year as a stripper (no, we aren’t joking), Diablo Cody wrote a blog and later a book titled Candy Girl: A Year in the Life of an Unlikely Stripper in 2005. With both becoming huge hits, Cody used her newfound fame to launch her career as a screenwriter and debuted her talents in 2007 in the award-winning film Juno. Since then, she has continued to shine as a writer and producer on hit television series and films such as United States of Tara, Jennifer’s Body and Paradise.
Nominated for an Academy Award for Best Original Screenplay in 2008 for Juno, Cody lived up to her wild side when she walked the red carpet in a leopard print dress. Much like Anna Nicole Smith’s turquoise Betty Rubble gown from earlier on the list, Cody wore her own Flintstone-inspired Pebbles dress that left fans and photographers wondering if she had a bone barrette for her hair to finish off the look. Though she might’ve been one of the worst dressed, that didn’t stop this wild woman from happily taking home the Oscar!
#7 – Charlize Theron
Just put a bow on it! Hailing from South Africa, 40-year-old Charlize Theron has spent nearly 20 years as one of Hollywood’s hottest and most talented actresses, producers and models. First working as a model at the age of 16, Theron made her film debut in a non-speaking part in 1995 only to land more and more prominent roles in the following years in blockbuster hits like The Devil’s Advocate, The Cider House Rules, The Italian Job and Mad Max: Fury Road.
Bringing a whole new meaning to massive shoulder statements, Theron stayed busy at the 2006 Oscars where she presented the Oscar for Best Documentary Feature in addition to being nominated for Best Actress in North Country. Arriving on the red carpet in a black Galliano Dior gown featuring a giant bow on her left shoulder, Theron may not have won an Oscar but she didn’t go home emptyhanded as the fashion police awarded her as one of the “Worst Dressed” of the night. Heck, she probably even needed an extra seat for her bow!
#6 – Charlize Theron
Perhaps not learning a big enough lesson (or missing it altogether) from her experience at the 2006 Academy Awards, the beautiful Charlize Theron appears on our list once again. Invited to present Precious as one of the nominees for Best Picture at the 2010 Oscars, Theron managed to shock her fans, colleagues and especially the fashion world long before she ever took the stage in this unique and distracting lavender gown by Dior.
Dubbed “The Cinnamon Bun” dress, Theron’s gown was beautiful from the back with a modest but exquisite train while the front of the gown featured two roses (or cinnamon buns) covering her chest. While many women joke that people sometimes stare at their chests rather than looking them directly in the eye, there’s no doubt that Theron experienced something similar as no one could focus on anything but her cinnamon buns when she took center stage! Maybe this time, she learned her lesson!
#5 – Trey Parker & Matt Stone
The world knows Stan, Kyle, Cartman and Kenny of South Park but how many people can recognize best friends and co-creators, Trey Parker and Matt Stone of Colorado? Responsible for 19 seasons of the tenth “Greatest TV Cartoon of All Time,” Parker and Stone have also moved beyond the fictitious world of South Park, Colorado by writing and producing the Tony Award winning musical The Book of Mormon and the television series, Team America: World Police.
Undoubtedly in their true element and making everyone laugh even on the red carpet at the 2000 Oscars, Parker and Stone went in drag as they tried to imitate Jennifer Lopez’s iconic dress from the 2000 Grammy Awards and Gwyneth Paltrow’s gown at the 1999 Oscars. Admitting they were on drugs at the time, the pals knew it would be a good laugh as Parker was nominated for Best Original Song for “Blame Canada” in the South Park movie, which is often considered one of the most underrated musicals of all time.
#4 – Sally Kirkland
Look! It’s a magician – or is it? Born in The Big Apple and raised in Oklahoma, Sally Kirkland returned to New York City in the early 1960s with the hopes of pursuing an acting career. Appearing in off-Broadway productions and later transitioning into small film roles, Kirkland got her first taste of success and fame when she starred in the 1987 film Anna, which earned her a Golden Globe. Now at 74 years old, Kirkland’s schedule has slowed down with her last appearance in the 2014 horror film, Suburban Gothic.
Known for always marching to the beat of a different drum, Kirkland’s unique sense of style surprised very few when she arrived at the 2007 Oscars in her latest fashion faux pas. Wearing a combination of a vampire costume, a magician’s cape and a parachute tent, the fashion critics had a field day with Kirkland who proudly embraced her “exploding tent” look and the glamorous evening. People didn’t pull any punches on poor Kirkland when they criticized her look as a throwback to the Count on Sesame Street. Now that had to sting a little!
#3 – Whoopi Goldberg
Forever making her mark in Hollywood in 1985 with her Academy Award nominated performance as Celie in The Color Purple, Whoopi Goldberg’s career spans 35 years and includes over a dozen Emmy Award nominations in addition to an Oscar, Grammy and Tony Award. How’s that for a career! Perhaps better known as a comedian and as the rule-breaking nun on Sister Act, Goldberg has spent the last nine years as the host and moderator of ABC’s hit daytime talk show, The View.
Well established as a star by the 1990s, Goldberg was asked to host the 1993 Academy Awards and, to celebrate the event, wore one of the most interesting dresses ever seen at the Oscars (and that’s a tall order to fill!). Goldberg’s gown resembled a tribute to The Wizard of Oz (or perhaps even to Mardi Gras) with its purple jacket and skirt opening into a lime green cape complete with a bodysuit underneath. Though intended as a fashion statement, little did Goldberg know that her outfit might later inspire Oregon’s football uniforms – hey, it could happen, right?
#2 – Lizzy Gardiner
A real world traveler, an artist and what some might call a modern-day gypsy, Australian costume designer Lizzy Gardiner has made her way around the world living in places like Wales and Florence. Perhaps one of the least known celebrities on our list, Gardiner has been in Hollywood since the 1990s and is one of the most popular costume designers thanks to her work in films like Ghost Rider, Mission Impossible II and Burning Man.
Nominated in 1995 for Best Costume Designer at the Academy Awards for The Adventures of Priscilla, Queen of the Desert, Gardner was a relative unknown going into the event but that would quickly change. Turning heads when she stepped out of the limo wearing 254 expired American Express gold credit cards, Gardiner said the dress was supposed to be used in the flashy film but the credit card company refused. Instead, she repurposed the dress for the Oscars where she not only won Best Costume Designer but made history for wearing one of the worst gowns in Oscar history. How’s that for making a first impression?
#1 – Bjork
Iceland sent the world a truly unique treasure in the late 1980s when the very eccentric and highly talented singer-songwriter Bjork made her debut. Initially rising to fame as the lead singer with the alternative band, The Sugarcubes, the band’s 1987 single “Birthday” was an international hit that gave Bjork the confidence to launch her solo career. Now at 50 years old, Bjork has been wowing audiences for the past 30 years and has earned 14 Grammy Award nominations, two Golden Globes and one Academy Award.
Winning yet another award, Bjork takes the top spot on our list as having one of the most memorable and hideous dresses in Oscar history. It’s so ugly that it even has its own Wikipedia page! In true Bjork fashion and always looking to make a statement with her art, Bjork had designer Marjan Pejoski create a swan-inspired gown and went so far as to pretend to lay an egg on the red carpet. Though Bjork is far from an ugly duckling, this dress is definitely one for the birds since only someone as unique as Bjork could pull off this Swan Lake fashion fail!