Awards ceremonies have a kind of magic. The brightest stars in Hollywood come together to walk the red carpet and show off incredible looks from the best designers in the world—except sometimes those looks aren’t so incredible. While taking a risk can certainly pay off, it often earns celebrities a spot on a worst dressed list. At least we can always say these looks were unforgettable.
Demi Moore’s 1989 Oscar Dress
While Demi Moore’s red carpet looks are usually chic and sophisticated, the St. Elmo’s Fire and About Last Night… star couldn’t escape the 1980s without one major fashion disaster. Moore showed up the 61st Annual Academy Awards with Bruce Willis looking a lot like she’d biked to the theater.
For the ceremony, Moore decided to try her hand at fashion design, and it’s safe to say she should stick to acting. The bizarre ensemble featured lace-trimmed bike shorts and plunging floral bustle. We do have to give Demi props for one things: we’ve never seen another Oscar dress like this one.
The Jane Fonda Versace Dress That Landed Her On Fashion Police
The gorgeous Jane Fonda found herself the target of Joan Rivers’ first ever episode of Fashion Police for E!. Rivers joked about Fonda’s black and white Versace dress saying, “We’re going to start with a beautiful, beautiful woman. I wish I could say the same thing about her dress.”
Rivers also took aim at the designer of Fonda’s Oscar dress, saying, “Gianni Versace—the man is Italian—I think he’s still [mad] that they lost the war.” We have to agree with Rivers on this dress. The oversized checkerboard pattern definitely wasn’t doing the lovely Jane Fonda any favors.
Kim Basinger’s Strange White Academy Awards Dress
Bond girl Kim Basinger can act, sing, and model—but it turns out she isn’t much of a designer. As a presenter at the 1990 Oscar ceremony, Basinger no doubt wanted to make an impression, but designing her own dress for the event might not have made the impression she was hoping for.
The white satin gown featured a giant skirt and a menswear inspired bustier with asymmetrical sleeves. The strange combination of a Cinderella skirt, wedding dress white, and an odd top made this dress one of the most memorable award show fashion disasters of all time.
Justin and Britney’s Double Denim Moment
The year was 2001. The place: the American Music Awards. It was then and there that Britney Spears and Justin Timberlake gave us a gift we will never forget: their iconic double denim ensembles. The pop princess and prince had been dating for two years when they strolled down the carpet hand in hand, clad in head to toe denim.
Though the couple broke up shortly after the awards, at least we will always have the memory of Justin Timberlake in that denim fedora, and Britney Spears in that plunging patchwork denim dress. This look did what so many fashion disasters fail to do: it transcended to that holy plane of existence called So Bad It’s Good.
Whoopi Goldberg Stands Out from the Crowd
Whoopi Goldberg has done it all. She’s starred in a variety of films, from period dramas like The Color Purple to romantic fantasy films like Ghost, for which she won an Academy Award. She’s a moderator and co-host of The View. She’s known for her balance of comedy and drama, and her outspoken, quirky personality. That’s why her bizarre 1993 Oscar outfit almost works.
While the paisley pantsuit and lime green and purple overcoat is definitely a fashion fail, Goldberg manages to wear it with enough excitement and whimsy that it’s almost charming. Sure, she looks like she just stepped off the set of a Broadway musical—but it’s Whoopi Goldberg, so why not?
Tyra Banks in a Purple Barbie Dress
Maybe Tyra Banks was still method acting when she showed up to the 72nd Annual Academy Awards in this purple tulle nightmare. The supermodel seems like she just walked off set of the television movie Life-Size where she starred opposite Lindsay Lohan as a doll that came to life.
The frou-frou gown by Vera Wang looked more appropriate for the prom than the Oscars red carpet. Then again, it was 2000, and Tyra Banks wasn’t the only one to ring in the new millennium with a few questionable fashion decisions. We’re glad this lavender disaster is in the past.
Celine Dion’s Backwards Suit
The Canadian “My Heart Will Go On” singer caused quite a stir when she wore a white Christian Dior tuxedo backward to the 1999 Academy Awards. The look was topped off by a jaunty hat and dark sunglasses.
While some might argue that Celine Dion was subverting the gendered expectations of how women should dress at awards shows, it’s likely that this was just another fashion faux pas. Perhaps the suit would’ve been a hit if she hadn’t chosen to wear it backwards. While this award show fashion disaster wasn’t a hit, at least Dion has plenty of hit songs.
Cher’s Skin-Bearing Ensemble
Cher has never been afraid to make a major statement with her fashion choices. It’s fair to say her dramatic, sequined, skin-bearing Bob Mackie ensemble at the 1986 Academy Awards stayed true to the legendary diva’s larger than life personality.
While this limelight stealing dress and feathered headpiece are arguably a fashion disaster, it’s impossible to deny that Cher had all eyes on her as she was presenting the Oscars. She even joked about receiving an Academy book on “how to dress like a serious actress.”
Miley Cyrus’s Circus Costume
As Jane Fonda learned long ago, the black and white checkerboard pattern is not an easy pattern to pull off. Unfortunately, Miley Cyrus fell prey to a similarly unflattering look at the 2013 Billboard Music Awards. The singer wore a Balmain jumpsuit featuring intricately woven pieces and an all-over checkerboard print.
Fashion critics were torn on Cyrus’ look, with some calling it bold and rocker chic, and others comparing it to a Cirque du Soleil costume. Whether or not the look was a daring departure or a fashion faux pas seems to be a matter of taste.
Geena Davis Channels Her Inner Cancan Dancer
Geena Davis’ dress from the 1992 Oscars, the year she was nominated for Thema and Louise, is one of the most notable award show fashion disasters. The strange bridal dress with a mullet skirt, elbow length white gloves, and black tights make Davis look more like she’s attending a costume party than the Academy Awards.
Of course, Davis could probably wear a wet canvas sack with a hole cut out for her head and still look gorgeous. This beautiful and talented actress might have missed the mark in 1992, but her future looks would prove to be much more chic.
Björk’s Iconic Swan Dress
Björk’s iconic swan dress, designed by Marjan Pejoski, has stirred up a lot of debate. While it may have seemed like a fashion disaster to those watching the 73rd Academy Awards at home, the dress received praise from designers and fashion blogs. However, some viewed it as a publicity stunt. The Boston Globe wrote that the dress made her “look like a refugee from the more dog-eared precincts of provincial ballet.”
The Icelandic singer is known for her boundary pushing fashion and experimental music, so if anyone could pull of this look it’s Björk. Whether you loved this dress or hated it, there is no denying it made a major impression.
Gwyneth Paltrow’s Sheer Oscar Moment
2002 Gwyneth Paltrow looks like she needs to get GOOP-ed. Her Oscar dress by Alexander McQueen had a see sheer top, and though Paltrow went without a bra at the Academy Awards, she later admitted she would have styled the look differently by covering up more and wearing less of Margo Tenenbaum’s eyeliner.
The late designer, Alexander McQueen, disagreed. He loved the way Gwenyth styled the look and said, “She looked incredible.” While fashion critics may disagree with the designer, there’s no question that this look was an attention-grabbing choice for the Oscars. We can’t imagine Paltrow wearing anything so punk now.
Anne Hathaway’s Problem With Darts
The normally chic Anne Hathaway ran into a little darting problem at the 2013 Oscars. Her adorable pixie cut that she sported after filming Les Misérables was perfectly styled. Her jewelry was simple, beautiful, and elegant. The soft pink Prada dress she wore even complimented her skin tone.
Unfortunately, a couple of awkwardly placed darts ruined the look, with Hathaway ending up on some of the year’s worst dressed lists. It just goes to show how a few stitches in the wrong places can make all the difference, especially when it comes to rocking satin fabric.
Angelina Jolie’s Goth Side
It’s hard to believe this super sophisticated actress used to dress like an eighth grader who shopped at Hot Topic. The year she won Best Supporting Actress for Girl, Interrupted, Angelina Jolie showed up to the 2000 Academy Awards looking more like she was auditioning for the role of Morticia Addams.
The actor wore a floor-length, black, long-sleeve gown, dark winged eyeliner, and slicked black hair. Jolie also kissed her brother, James Haven, after the ceremony, which had everyone talking. On the kiss, Jolie said, “It was so disappointing that something so beautiful and pure could be turned into a circus.”
Uma Thurman Gets Lost in Fabric
Uma Thurman’s Amazonian frame deserved to rock something so much better than her 2004 Oscar dress. The actress cites the Christian Lacroix nightmare dress as her “most embarrassing experience,” and it’s easy to see why.
The lacy, floor length dirndl dress was accented by a bright blue satin ribbon and a bizarre gold waistcoat. Though she kept her hair and make-up simple, the part-peasant, part-Grecian dress hid the Kill Bill star’s phenomenal beauty under sagging layers of fabric. Let’s face it: if Uma Thurman can’t pull off a dress, then no one can.
Joy Villa’s Rib Cage Look
The 2016 Grammy Awards red carpet was full of some of the best dressed celebrities in the music industry, and then Joy Villa, better known by her stage name Princess Joy Villa, showed up. The American singer and songwriter sported one of the strangest looks of the evening.
Villa is known for her wild looks, so this spiky number didn’t disappoint fans who wondered what she would wear next. Unfortunately, the skin bearing ensemble grabs attention in the worst way, and makes the singer look like one giant robotic rib cage. Clearly, the description “show-stopping” doesn’t always have a positive connotation.
Jessica Biel’s Just Rolled Out of Bed Look
Jessica Biel, known for her roles in The Rules of Attraction, Total Recall, and Blade: Trinity, looked a lot less like her radiant self at the 2009 Academy Awards. The actress showed up in strapless white dress that had fashion critics scratching their heads.
The dress looked like a set of bed sheets folded around the actress, with a large piece of fabric at the top that looked like a deflated balloon. The underwhelming look could’ve used some serious help from a good tailor. It’s almost hard to believe a stylist picked out the unflattering dress for her.
Halsey’s Futuristic White-Out Jumpsuit
The American Music Awards tend to be a place where musical artists experiment with their looks, but sometimes they don’t quite hit the mark. That was the case for the talented Badlands singer, Halsey, at the 2016 American Music Awards.
Halsey sported a shaved head and a skin tight white pleather jumpsuit. While we’re sure her stylist was going for something futuristic and spotlight stealing, the singer looked more like she was covered head to toe in White-Out. The white pleather looked a little cheap—like the costume for an extra in a science fiction B-movie. Better luck next time, Halsey.
Dani and Bella Thorne’s Red Carpet Miss
Halsey wasn’t the only one that struggled with her fashion choices at the 2016 American Music Awards. Sisters Dani and Bella Thorne walked the red carpet together in two equally awful outfits and matching red and green hair.
Sporting a thin silver dress, a bra as a top, some truly terrible green locks, and a liberal amount of glitter, the sisters look more like they’re stumbling home after a nightmare weekend in Los Vegas after a wild bachelor party than walking the red carpet. The only thing that makes these outfits any better is that it’s possible the pair were in on the joke.
Jennifer Connelly’s Dishwater Dress
The original queen of thick brows, Jennifer Connelly, can’t even pull off her 2002 Oscar dress. Connelly’s win of the evening was winning Best Supporting Actress for A Beautiful Mind. Her loss was the dreadful dress.
The dirty dishwater color washes out the star, and an unflattering cut makes Connelly look like she’s wearing one large compression garment around her body. This natural beauty can pull off a lot, but no one could rock this look. Fortunately, the Academy Award win is forever, and this dress was just for a day.