Celebrity Outfits That Nearly Put Their Careers In Jeopardy

In the world of entertainment, image is everything. When something about a performer's image goes awry or the public perception is not what it is expected, the resulting impact on their career can be profound. Whether it has been on the red carpet, during high-profile performances, on stage at the most prestigious award shows, or in their daily lives, many celebrities have fallen prey to the negative fallout that occurs when an outfit misses the mark. Like when Björk wore a faux swan dress to the 2001 Academy Awards — and then proceeded to make the fashion moment even more bizarre when she simulated the laying of six large eggs.

There was also the time Doja Cat rolled up to the Schiaparelli Haute Couture show in 2023 with her body covered with red crystals to match her dress. Here are 11 other celebrity looks that stopped the presses and impacted the way the stars who wore them were perceived in terms of their careers and overall public perception (an inordinate number of which came during appearances at MTV's Video Music Awards over the years).

Perhaps the ultimate example of an outfit choice having major ramifications, Janet Jackson's style — or, at the very least, what she and Justin Timberlake elected to do with it — during the halftime show at Super Bowl XXXVIII in 2004 ended up being one of the most controversial moments in U.S television history. Heading into the event, which saw the New England Patriots take on the Carolina Panthers, Jackson, Timberlake, and a lineup that included Jessica Simpson, P. Diddy, Nelly, and Kid Rock, seemed like a can't-lose scenario. However, as the halftime show ended, Jackson's right breast and nipple (which was adorned with an ornamental shield) were exposed to the viewing world.

The "wardrobe malfunction" stunt, or fumbled costume reveal (depending on who you talk to) drew the ire of FCC chairman Michael Powell, who described Jackson baring her chest as "classless, crass, and deplorable." It also generated a nationwide debate about what is appropriate for television viewing. The halftime performance should have gone down as a career highlight for Jackson and Timberlake, but the discourse surrounding the game and the show continues to revolve around an exposed breast. Meanwhile, CBS — the network that aired the Super Bowl and its halftime show that year — received a massive $550,000 FCC fine. In the end, the fine was thrown out by the courts, but the moment has lived on in infamy.

A couple of decades in, the Kardashian-Jenner clan remains at the forefront of the celebrity world, and Kim Kardashian continues to make headlines, and there have been some reputation-harming, career-hindering missteps along the way. One such misstep was her decision to wear Marilyn Monroe's iconic "Happy Birthday, Mr. President" dress to the 2022 Met Gala. The sheer, rhinestone-emblazoned garment that Monroe wore when she famously sang to President John F. Kennedy was loaned to Kardashian by the Ripley's Believe It Or Not Museum, which purchased it at auction for $4.8 million in 2016.

Alas, even though Kardashian didn't actually wear the iconic dress for as long as you might have thought, photos of the garment in the wake of the event seemingly revealed stretched fabric, new holes, and dangling crystals. Even now, she continues to receive criticism. During a 2024 screening of the documentary "Bob Mackie: Naked Illusion," Mackie — who designed Monroe's dress — was asked how he felt about Kardashian wearing it out. He reportedly answered by putting the question to the crowd, which booed vociferously, after which he declared, via Page Six, "Wrong is wrong!"

The year 1999 was the golden age for a particular brand of hip-hop and R&B music, and Lil' Kim was at the forefront. So, when the rapper-singer-songwriter rolled up to the MTV Video Music Awards in 1999, it was perhaps apropos that she did so in an outfit that demanded the attention of the event's attendees, as well as the millions watching from home via their television sets. The "Not Tonight (Ladies Night)" performer showed up at the red carpet in a single-sleeved lavender jumper that left the left side of her upper torso almost bare, with nothing but a bedazzled pasty partially covering her breast on that side. The controversial VMAs outfit elicited strong reactions, both positive and negative, from fans and pundits.

Kim's outfit was so wild that when she later joined Mary J. Blige and legendary songstress Diana Ross on stage to present the award for Best Hip-Hop Video, Ross found herself totally transfixed to the point that she was compelled to juggle Kim's exposed breast on live TV. "I had no idea that Diana Ross was going to fondle her. That was a nerve-racking moment," Kim's stylist Misa Hylton told PopSugar in 2020. The look has since been replicated by the likes of Miley Cyrus and Nicki Minaj, but it remains controversial in the eyes of the more conservative pop culture consumers.

While Lady Gaga is about as mainstream as mainstream gets these days, there was a time when she was still a fledgling star on the proverbial rocket ship upward, and many didn't know quite what to make of her. That mystique was boosted by the occasionally bizarre and surrealist ways in which she elected to present herself to the public. The highlight of this early relationship with fans and critics undoubtedly came during the 2010 MTV Video Music Awards when she decided to attend the show in a dress hewn from literal raw meat. She didn't stop at the dress, either, turning up with boots and a clutch that were similarly made from raw Argentinian beef. 

The look drew the ire of animal rights groups, including PETA, which wrote, "Meat is the decomposing flesh of a tormented animal who didn't want to die, and after a few hours under the TV lights, it would smell like the rotting flesh it is and likely be crawling in maggots — not too attractive, really." Even the designer heard from anti-meat groups in the aftermath of the moment. Nevertheless, it remains etched in the memory of those who saw it, and new audiences are discovering it all the time as the dress was later preserved and displayed at the Rock and Roll Hall of Fame and the Haus of Gaga in Las Vegas.

After several decades in the entertainment business as a singer, actress, and veritable icon of pop culture, it's hard to imagine a time when Cher was looked at as anything but the shining example of what a performer aspires to be. However, there were definitely times throughout her lengthy career, even after she had achieved an incredible level of fame, when she wasn't getting her due or when she felt she was still proving herself. Such was the case in 1986 when she thought the organization behind the Oscars, the Academy of Motion Picture Arts and Sciences, wasn't showing her the proper respect as an artist. So, how did she respond to this perceived slight from one of Hollywood's most powerful groups? By throwing its alleged disdain right back at it.

Cher attended the 1986 Academy Awards in a black Bob Mackie-designed dress that looked like something out of a Las Vegas burlesque show, with a bedazzled feather headdress to match. "I had the idea mostly because the Academy didn't really like me," Cher told Vogue in 2019. "They hated the way I dressed, and I had young boyfriends. So, they thought I wasn't serious. So, I came out and said, 'As you can see, I got my handbook on how to dress like a serious actress.'" Perhaps no star has poked the bear with such style.

There was a time during the mid-to-late 1990s when Rose McGowan, whose life has taken some tragic turns, was an indie darling, starring in low-budget and under-the-radar gems like 1995's "The Doom Generation," 1997's "Going All the Way," and 1999's "Jawbreaker." However, she went on to become a household name with her role as Paige Matthews during the final seasons on the WB series "Charmed." Before she was able to etch herself into the annals of sci-fi/fantasy lore with that performance, though, McGowan was heavily criticized for wearing a barely-there fishnet/chain-style dress with only a thong beneath it to the 1998 MTV Video Music Awards as she walked the red carpet with her then-partner, Marilyn Manson. While some praised the daring look, the decency police were also out in full force.

McGowan later said the criticism was a lot to contend with. "It was kind of hard. I hadn't really ever dealt with global media shaming. But it prepared me for, later on, it happening to me a whole bunch. It was also like, 'Sorry you're square and I'm not — bummer!'" she told Yahoo! in 2023. "I'm like, 'Why did I do that?' I've had to look at that." She further revealed that she wore the revealing dress as a means to reclaim her own body following an alleged assault at the hands of Harvey Weinstein the prior year, but that subtext was unfortunately lost on the commentators of the day.

Sometimes, a celebrity outfit goes viral to such a degree that it ends up with its own Wikipedia page. Such is the case for the green Versace silk chiffon dress actress/singer Jennifer Lopez wore to the Grammy Awards in 2000. Over the years, the look has come to be recognized as one of the most iconic looks of the era, and one of the fits that put designer Donatella Versace on a tier befitting her name. At the time, though, not everyone was a fan, and Lopez herself experienced a level of personal blowback from wearing it. The outfit was lampooned by the likes of former Today show host Matt Lauer and South Park co-creator Trey Parker, as documented in Lopez's 2022 documentary, "Halftime."

"It was hard when you think people think you're a joke, like you're a punch line," Lopez said in the doc about the focus on her body when she wore the dress, via Business Insider. "No matter what I achieved, their appetite to cover my personal life overshadowed everything that was happening in my career," she said earlier in the doc of the media coverage she received at the time. "I just had very low self-esteem. I really believed a lot of what they said, which is, I wasn't any good, that I wasn't a good singer, I wasn't a good actress, I wasn't a good dancer. I wasn't good at anything."

In hindsight, some of her controversial performances appear relatively tame when viewed through the modern lens, but make no mistake, Madonna pushed hard against the barriers of what was then considered appropriate during her '80s and '90s heyday. Between her music and provocative performances, the "Like a Virgin" singer regularly found herself in the crosshairs of groups who believed strongly that her influence would lead the youth of the day down a path of immorality, and she felt the pressure. Case in point: the outfit she wore while performing the aforementioned 1984 hit at the MTV Video Music Awards. That night, she hit the stage in a wedding dress while singing about being "touched for the very first time."

If that wasn't controversial enough, she also suffered a wardrobe malfunction during the performance. Specifically, her pumps fell off, and her backside was flashed as she retrieved them. "Those were the days when you shouldn't show your butt to have a career," Madonna explained to Jimmy Fallon in 2022, via People. "Now it's the opposite. I didn't even know my butt was showing!" Apparently, that was her stylist Maripol's concern, too. "I was right there. I saw it happening. I saw what [MTV] did, and I can tell you that they tried to destroy her that day," Maripol said in 2019, via Yahoo!. "They went under her skirt with the camera."

As with Jennifer Lopez, sometimes a controversial or viral celebrity outfit can affect their self-image. Miley Cyrus experienced this with her look and performance at the 2013 MTV Video Music Awards. At the show, Cyrus shared the stage with Robin Thicke, sporting a latex bra and matching bottoms while rubbing up against the "Blurred Lines" singer during their joint performance. In 2018, Cyrus said her life changed forever after the performance, which forced her to rethink her career and even her everyday wardrobe.

"I basically went through two or three years where I wouldn't wear shorts. I stopped wearing skirts on stage, all this s**t because after the VMAs — and I had on my cute little nude bodysuit — everyone started comparing me to a turkey and putting a turkey in my outfit," Cyrus recalled during an Instagram Live chat, via Entertainment Tonight in 2020. "I was just so skinny and so pasty, and they kept putting me next to this turkey, and I was feeling so bad on myself that I did not wear a bikini for like two years ... It was just really, really hurtful to be so body-shamed like that. And it really affected me in my personal life."

Celebrity stylist and content creator Jamie Azzopardi found themselves in hot water in 2025 after wearing a dress from the fast-fashion brand Shein to Australian Fashion Week. The $70 brown/maroon fringed frock appeared to be a knock-off of a Hervé Léger gown that retails for over $3,000, which drew criticism from other event attendees. The fact that Azzopardi was wearing Shein at all during the event also seemed like an affront to the event itself, as Aussie Fashion Week 2025 espoused better industry practices, inclusivity, and sustainability. Meanwhile, Shein had previously come under fire for building its brand on the backs of poorly-treated workers at factories in China. "If there are 31 days in a month, I will work 31 days," one worker told the BBC of their experience.

The dress was ultimately used as ammunition by Sophia Begg and her fans in a feud that emerged after Azzopardi referred to her as a "mico-influencer boss" at the event, via the Daily Mail. In the wake of their perceived Fashion Week misstep and feud with Begg, Azzopardi effectively disappeared from Instagram for months.