When the red carpet rolls out at a Hollywood awards ceremony, it becomes a catwalk for wearable art. Journalists interrogate musicians and actors about “who they’re wearing,” and commentators assess red carpet looks and decide if they’re “hot or not.” In recent years, social media has provided another layer of public judgment and commentary; the common spectator can now let the entire internet know how they feel about the “fashion fail” of the evening. While everyone enjoys seeing a celebrity wear an objectively stunning, albeit safe gown to an award show or gala, the looks that stay lodged in our memories for years are the ones that are most off-the-wall.
What makes a memorable red carpet fashion moment? Sometimes, it’s a bold ensemble that only the wearer could make work. Other times, a look nabs headlines because it malfunctions in front of the cameras or intentionally shows off a significant amount of skin (Rose McGowan’s nearly-naked 1998 VMAs look is so revealing that even a censored photo can’t be pictured on this list). There are award show outfits that have stuck with us because of the memes they inspired, the political religious statement they made, or the materials used. But the one thing all of these looks have in common? They got people talkin’.
Fashion is art, and as Madonna told The New York Times in 1989, “Art should be controversial.” On that note, let’s get into some of the most jaw-dropping outfits worn by celebrities at award shows.
Madonna 'shocked' audiences at the 1984 VMAs
On Sept. 14, 1984, then-26-year-old up-and-comer Madonna took the stage at the first annual MTV Video Music Awards to sing “Like a Virgin.” She wore an all-white bridal look, complete with a rosary necklace, a white lacy bustier, and a belt that said BOY TOY.
As Madonna descended a 17-foot-tall wedding cake, one of her white stilettos slipped off. When she reached for it, her dress rode up, flashing her underwear to VMA viewers. She finished the performance by writhing around on the floor. “People came up to me and told me her career was over before it started,” Madonna’s publicist Liz Rosenberg told Billboard.
In reality, the night was only the beginning for the headline-grabbing Queen of Pop. “I knew that [VMAs] day that she had made it,” Madonna’s stylist, Maripol, told Yahoo! Entertainment. “Every journalist was rushing, running, going, ‘Oh my God, who is this girl with the white outfit rolling and crawling on the floor, with crosses in her ears and her name is Madonna? And she’s singing about being like a virgin?’ They were shocked.”
Cher took peacocking to a new level
Cher has long been celebrated for her show-stopping showgirl style, harnessed with the help of her longtime costume designer Bob Mackie. If you think the Goddess of Pop’s 1986 Oscars ensemble was over-the-top, Mackie is right there with you. “I told her, ‘You can’t dress like that to give somebody an award, you’ll pull all the focus from them,'” he told People. “And she said, ‘Oh, they won’t mind.’ Then there she is, and she’s on the cover of every newspaper all across the country.”
The midriff-baring look featured a black beaded skirt and bra, topped off with a feathered headpiece fit for a goth cockatoo. The look raised eyebrows and drew headlines. “People liked it and hated it at the same time,” Mackie said. “Critics said, ‘Well, that’s not fashion.’ Well, it wasn’t meant to be fashion. She wanted to do it just because it was fun.”
For Cher, overshadowing her surroundings was part of the thrill. “I had the idea mostly because the Academy didn’t really like me,” Cher said in a Vogue video. “They hated the way I dressed… So I came out and said, ‘As you can see, I got my handbook on how to dress like a serious actress’.”
Lil' Kim's 1999 VMAs sure grabbed attention
Lil’ Kim’s 1999 MTV Video Music Awards look let purple reign. The rapper wore a lilac, one-shoulder jumpsuit that left her left breast exposed, save for a sequined nipple pasty. “I wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out,” the rapper’s stylist Misa Hylton told Popsugar. When Lil’ Kim presented an award alongside Diana Ross and Mary J. Blige, Ross flicked Lil’ Kim’s exposed breast. “I was really pissed when that happened,” Blige said on Watch What Happens Live with Andy Cohen in 2020, “because that’s my little sister and my friend.”
Lil’ Kim was less bothered by the incident. “A lot of people were like, ‘How did you feel?’ But honestly, I think she was just giving me a little motherly tap,” she told Carson Daly in 2002. “Like, ‘Girl, do you know you got a boob hanging out?'” Two decades later, the outfit’s impact lingers on. Many people thought Kylie Jenner channeled the outfit at the 2019 Met Gala, and Miley Cyrus payed homage on Halloween in 2013. “I wish I was there to squeeze your boob,” the rapper joked on Twitter in response to Cyrus’ costume.
The Jennifer Lopez moment that changed the internet
Jennifer Lopez did not take home any awards at the 42nd Annual Grammy Awards in 2000, but she stole the show nonetheless. The singer/actor wore a Versace dress made of sheer silk chiffon and covered in a palm frond print, with a below-the-navel neckline and bejeweled underwear underneath. It was designed by Donatella Versace, who had recently taken over the legendary label following the death of her brother, Gianni Versace. The barely-there dress marked her arrival, becoming one of the fashion house’s most iconic designs to date. J. Lo donned the dress again at the Versace Spring 2020 fashion show. “The second time I wore it and walked out there, it was such an empowering thing,” Lopez told Vanity Fair. “Twenty years had gone by, and I think for women, knowing you can put on a dress 20 years later—it resonated. It was like, ‘Yes, you know, life is not over at 20!'”
The dress was the reason Google Images was invented… literally. “People wanted more than just text,” former Google CEO Eric Schmidt wrote on Project Syndicate in 2015. “This first became apparent after the 2000 Grammy Awards, where Jennifer Lopez wore a green dress that, well, caught the world’s attention. At the time, it was the most popular search query we had ever seen. But we had no surefire way of getting users exactly what they wanted: JLo wearing that dress. Google Image Search was born.”
Björk proved she was a rare bird at the 2001 Oscars
Björk’s 2001 Academy Awards dress ruffled a few feathers. Created by Macedonian designer Marjan Pejoski, the garment featured a white tutu; a sheer, bejeweled, nude body stocking; and a faux swan draped around her neck. “Not everybody understands my style,” Pejowski told Vogue. “But I don’t care about bad publicity. If you are an artist you don’t expect everyone to love what you do. And anyway, I love that there has been such an issue. How awful if nobody had noticed the dresses, or made any comment about them.”
The swan dress has topped countless worst-dressed lists has been parodied everywhere from Hannah Montana to Kevin James’ 2002 People’s Choice Awards look. The ensemble wasn’t the only thing that solidified the Icelandic singer’s offbeat-but-iconic status at the 2001 Oscars; as CNN recalled, she was spotted “laying” six ostrich eggs on the red carpet. “I was very aware when I went to the Academy Awards that it would probably be my first and last time,” she told CDNow. “I thought my input should really be about fertility, and I thought I’d bring some eggs.” While the conversation surrounding the look has not focused on fertility, Björk’s swan dress is one of the most memorable looks in pop culture history.
Lady Gaga's meat dress was a little undercooked
“I never thought I’d be asking Cher to hold my meat purse,” Lady Gaga said as she took the stage at the 2010 Video Music Awards and… asked Cher to hold her meat purse. The “Bad Romance” singer wore a dress that was so avant-garde it made the risqué Goddess of Pop look tame in comparison. Designed by Argentine designer Franc Fernandez, the gown was made of raw flank steak and paired with matching beefy shoes. Fernandez confirmed to MTV that he made the dress from real meat from his family’s butcher in the Los Angeles valley.
Unsurprisingly, Gaga’s meat dress angered animal rights activists. “Wearing a dress made from cuts of dead cows is offensive enough to elicit comment,” wrote PETA founder Ingrid Newkirk, “but someone should whisper in her ear that more people are upset by butchery than are impressed by it.”
As for the ensemble’s odor? “Gaga said it smelled good,” Fernandez shared. The dress was ultimately made into beef jerky—yes, really. As The Los Angeles Times reported, a taxidermist was brought in to preserve the frock for the Rock and Roll Hall of Fame.
Some wanted to throw holy water on this Nicki Minaj look
While many of the outfits on this list are controversial for showing too much skin (or meat), Nicki Minaj’s 2012 Grammys ensemble may be one of her least revealing red carpet looks ever. The rapper wore a red hooded cloak-dress by Versace and walked the red carpet arm-in-arm with a man who, as The Hollywood Reporter noted, was dressed like the Pope or a bishop. The Pope-a-like also appeared in a pre-taped segment that showed him performing an exorcism during Minaj’s on-stage performance, which included stained glass, choir boys, and levitation.
Some deemed Minaj’s outfit and performance sacrilegious. In response, the Catholic League for Religious and Civil Rights published an essay titled, “Is Nicki Minaj possessed?” The verdict: “Whether Minaj is possessed is surely an open question.” The piece also called out “the irresponsibility of The Recording Academy,” before adding, “It’s bad enough that Catholics have to fight for their rights vis-à-vis a hostile administration in Washington without also having to fend off attacks in the entertainment industry.”
Angelina Jolie and the Leggy Black Dress
A little black dress has long been a fashion staple and a safe bet for simplicity and elegance. On first glance, the floor-length black Versace dress Angelina Jolie wore to the 2012 Academy Awards was pretty straightforward. But Jolie proved that it’s not what you wear, but how you wear it when she posed with her leg conspicuously poking out of the dress’ high leg slit. Onstage at the ceremony, writer Jim Rash imitated the pose while accepting the award for Best Adapted Screenplay. Within hours of the red carpet appearance, a now-defunct Twitter account called @AngiesRightLeg that, as AdWeek reported, amassed thousands of followers. The dress launched a million “legbombing” memes, such as photoshopped images of Jolie’s leg on RoboCop and on the moon.
Jolie later defended the commanding presence of her right leg to Extra. “I had a more complicated dress and I wore the more comfortable dress,” she said. “I think when you feel comfortable, when you feel yourself… you embrace it. And sometimes, maybe it appears to be a thing, I don’t know.”
Miley Cyrus' 2015 VMAs looks drew eyeballs
Miley Cyrus has never been afraid to make bold choices, but her many looks as the host of the 2015 Video Music Awards delivered more sartorial shock than usual. As Rolling Stone recapped, the singer arrived on the red carpet in a bejeweled silver belt, suspenders, and thigh-high boots… and not much else. She went on to wear several nearly-naked looks, including a clear Mamadoux dress with strategically placed bubbles, a cut-out dress that was more cut-out than dress, and a Versace bra that left little to the imagination.
Still, some of her most controversial looks drew criticism not for lacking fabric, but for lacking originality. The cartoonish, eyeball-themed getups Cyrus and her backup dancers wore throughout the night were reminiscent—or rip-offs—of then-popular designs by Australian fashion house Discount Universe. The label’s designers, Cami James and Nadia Napreychikov, responded in a now-deleted Instagram post (via The Sydney Morning Herald). “We are obviously distraught,” they wrote. “We are trying our best to rise above and stay focused. We’ve kept our mouths closed about a lot of things in the past, but the one thing you can’t TAKE and get away with is someone’s IDENTITY.”
Apparently, it’s all glittery water under the neon-coated bridge. The following year, the designers told Fairfax Media (via The Sydney Morning Herald), “We just continued doing our work, and it seems like she did too. It’s important to keep moving forward.”
Joy Villa's views are on her sleeves, purses, and skirts
Expressing controversial political views may be the biggest sartorial risk of all. Singer Joy Villa has turned her political statements into fashion statements on multiple Grammys red carpets over the years. As Billboard reported, she wore a “Make America Great Again” dress to the 2017 Grammy Awards to showcase her support for President Donald Trump. The following year, she wore an anti-abortion dress, that, as Variety noted, was “painted with a rainbow fetus” and carried a purse that read “Choose life.”
Villa drew inspiration for her 2019 Grammys look from Trump’s controversial plan to build a wall along the United States’ southern border in an attempt to discourage immigration. As People put it, the gown featured “a literal border wall” print and barbed-wire shoulder details. And in case all of that wasn’t explicit enough, the words “Build the Wall” were scrawled across the back of the skirt in lettering similar to the font used on Pink Floyd’s The Wall album. Villa showed up to the 2020 Grammys in her, as The Hollywood Reporter noted, “third pro-Trump fashion statement” when she wore a red, white, and blue ensemble that said “Trump 2020” and “Impeached and Re-elected.” In a now-deleted tweet (via USA Today), Villa said that the social media backlash that ensued “would be heartbreaking if it weren’t so over the top hilarious.”
Many said yee-naw to Noah Cyrus' 2020 CMT Awards getup
After the 2020 Country Music Television Awards, it was Noah Cyrus’ outfit, not her music, that made headlines. While performing her song “This is Us” with country singer Jimmie Allen, Cyrus wore a bejeweled cowboy hat and thigh-high Jeffrey Campbell boots, along with a sheer nude bodysuit by Saga NYC that created the illusion that she was wearing nothing but a barely-there, bedazzled bikini.
The country-glam look drew a slew of social media criticism, with Twitter users deeming it “trashy” and “tasteless” (via PopBuzz). Cyurs fired back at her critics on the platform, tweeting, “My body my choice, b**ch,” and “Honey, your granddaughter will wear that someday.” She also criticized Fox News on her Instagram story: “It’s skin tone underwear but thanks for blurring my thighs.” Noah has previously spoken out about living in sister Miley Cyrus’ shadow, but edgy fashion choices clearly run in the family.
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