The Most Awkward Award Show Wardrobe Malfunctions Ever

Anyone who spends part of their lives in front of cameras and on red carpets knows that wardrobe malfunctions are an eventual inevitability. A gust of wind or a miscalculated step can suddenly become a collective memory that floats around tabloids for decades. And the more daring the fashion, the more likely a mishap might take place.

But no matter how much prep, planning, and double-sided tape is involved, there’s always going to be something that happens. Hey, we’ve all been there, it’s just that most of us aren’t being endlessly photographed or doing live events. For example, Khloé Kardashian had a shirt tear backstage before she appeared on “The Ellen DeGeneres Show.” “I was wearing a shirt and backstage, the holes on the back [of it] ripped open,” she told People. “And I was like, ‘I don’t have anything to wear and it’s live TV!'”

She quickly sorted it out, however. “I ended up putting on a really baggy blazer and I looked really menswear chic,” Kardashian said. “But the whole time, I’m kind of scrunched over because I don’t really have a top underneath. I’m like, ‘Oh my gosh, what’s happening?'” Unfortunately for the celebs, though, not every situation ends with such a stylish fix, and some are caught in public with no chance for mending the problem. Yet we’ve got to admire the grace with which these celebs made their way through these awkward situations.

Venus Williams and her plunging dress at the Oscars

Venus Williams suffered a nip slip at the 2022 Oscars while wearing a white Elie Saab gown with a plunging neckline, per the New York Post. On the red carpet, the gown fit perfectly and Williams looked absolutely stunning. The problem came, however, when she sat down next to her sister, Serena Williams, and had a nip slip.

Williams quickly covered her chest with her arm, but not before cameras and viewers noticed the problem. Amazingly, Williams’ wardrobe mishap wasn’t the wildest thing to happen that night. The 94th Oscars will forever be remembered as the night Will Smith slapped Chris Rock, so Williams can rest assured that the infamous altercation will get a lot more airtime than her moment. Nevertheless, the good people of Twitter couldn’t resist chiming in about all the chaos that evening. “Oh my god and a Venus Williams nip slip,” one person tweeted. “This Oscars has become an episode of ‘The Jersey Shore.'”

Ironically enough, Smith won Best Actor for his role in the film “King Richard,” which was about the Williams sisters’ father and the story of their lives, though some felt that Smith’s slap overshadowed the special night for the tennis family. “That was supposed to be an Oscar representing Serena and Venus [Williams] and their family, and that moment has also been spoilt for them!” one person wrote on Twitter. But then again, the nip slip could have overshadowed that on its own!

George Clooney to the rescue

It’s hard to remember a time when George Clooney wasn’t married to Amal Clooney, but way back when, the silver-haired fox was a bonafide bachelor with a rotating series of dates. In 2010, Clooney arrived at the Oscars with Italian actor Elisabetta Canalis, according to the New York Post. Clooney had been nominated for his role in “Up in the Air,” but didn’t take home the award.

Canalis wore a Cavalli dress to the event and, right before they were scheduled to walk the red carpet, the zipper of her dress tore. Celebrity hair stylist Jonathan Antin was working on Canalis’ ‘do when this happened and he later spoke about it on “Today.” “I’m doing Elisabetta’s hair and the back of her dress, her zipper, broke open,” Antin explained. “The assistant jumped in with a needle and thread and started sewing the back of her dress.”

Clooney soon arrived and calmly took charge. “Hold on a second,” Antin revealed Clooney said to the assistant. “I have experience with this. I used to work on suits, honey.” Then Antin explained that Clooney took the needle and thread and began working on Canalis’ zipper. “I got to tell you something, he did an amazing job at cross-stitching,” Antin added. Al Roker joked, “As if there isn’t enough reason to hate George Clooney. He does it all, and he can sew. He makes his own clothes.” He does seem talented at everything!

Alicia Keys lost a heel

Alicia Keys suffered a wardrobe malfunction and no one even knew about it, that’s how smooth our girl is at performing. Keys was presenting an award with Zac Efron at the 2009 Academy Awards when one of the heels broke on her Jimmy Choo shoes as she was walking on stage, per the New York Post.

While the rest of the world didn’t see it, an assistant who was behind the scenes saw the whole thing and told the Post, “[Keys] walked on the ball of her foot so that nobody would know what had happened under her long dress. She was very calm and professional.”

As Keys has opened up about her past, she’s also mentioned how fashion was a huge part of her survival. “Growing up in these Hell’s Kitchen streets taught me A LOT,” she tweeted in part in March 2020. “I realize there’s a certain amount of armor u have to wear just to make it down the street.” In an interview with The Guardian, Keys spoke about her decision to dress casually to deflect any kind of attention. “Put me in some jeans and sneakers and I just feel so good,” she explained. “I grew up in a very, very, very … difficult area. First you needed … to be ready to run and secondly, you just needed to [dress in a way] to diffuse that … that ‘energy.'” Clearly, a broken heel was no match for this girl’s fire.

Jenny McCarthy wore a dress backwards

Jenny McCarthy had an unfortunate moment at the 1997 Oscars when she wore a Valentino dress backward. Oops! Before she realized something was wrong with the outfit, McCarthy told Us Weekly that she “felt like a million dollars.” However, she did notice that something seemed off. “I was wondering why it was so tight in the boobs,” she said, according to the New York Post.

It ended up being Valentino himself who told McCarthy about her error. “I didn’t realize I was wearing it backwards till Valentino came up to me at the Vanity Fair party and said, ‘Darling, you’re wearing my dress backwards,'” she added, per the Post.

But the embarrassment led to a wonderful friendship. The late comedian Joan Rivers, who was famous for her scathing-yet-honest critique of red carpet looks, labeled McCarthy as one of the worst dressed people of the evening. But the unfortunate award meant that McCarthy and Rivers became friends. When speaking about the situation on “The View,” McCarthy recalled Rivers told her, “She said, ‘Honey, listen, if I’m choosing you as worst dressed, it means you’re in the now. It means you kind of made it. So just shut up and deal with it,'” (via Entertainment Weekly). McCarthy added, “I had the privilege of winning an award from her and have been friends with her since.” What a happy outcome to a hilarious mistake.

Gwyneth Paltrow’s gothic gown

Gwyneth Paltrow got roasted for an Alexander McQueen dress that she wore to the 2002 Academy Awards. The dress featured a heavy black skirt that was contrasted by a sheer top that was a little overly revealing. She finished off the look with a tight braid updo and thick eyeliner.

While McQueen himself said that Paltrow “looked incredible,” per StyleBistro, others didn’t think so highly of the look. Some felt it was too harsh, while others thought a bra would have made it less distracting. “Celebs surround themselves with sycophants,” a source told the New York Post, “and nobody wanted to be the one to tell her how dreadful she looked, or to put on a damned bra.”

Years later, during a GOOP Q&A, Paltrow admitted she had a few regrets about the dress. “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup,” she said, (via Today). “Then, it would have worked as I wanted it to — a little bit of punk at the Oscars.” In 2021, Paltrow gave Vogue her perspective on the dress in hindsight. “Everybody really hated this [dress] … but I think it’s kind of dope,” she said. “I’m into it.” Paltrow added, “I had a weird hangover about it for a while because people were really critical.” But she held her ground and said she still liked the dress.

Oprah Winfrey’s dress mishap

Oprah Winfrey attended the 1986 Oscars when she was nominated for “The Color Purple.” While the nomination was a happy moment, Gayle King wrote in The Hollywood Reporter that Winfrey was hoping she wouldn’t win.

While she might be the only person ever to pray not to win an Oscar, King explained that it was because Winfrey had a dress disaster. “She was petrified and mortified because she had this dress, and the day before the Oscars she tried it on and it was too big,” King wrote. “So she asked the tailor to come and take it in. He then made it too small. And she discovered that an hour before the show.” All that Winfrey kept thinking was, “Please don’t call my name, please don’t call my name, please don’t call my name,” according to King. Luckily for Winfrey, Anjelica Huston ended up snatching the prize for her performance in “Prizzi’s Honor.”

Winfrey recalled the horrifying experience on “Jimmy Kimmel Live” in 2012 and explained that she solicited Dolly Parton’s dressmaker for the occasion, but didn’t get a chance to try it on after changes were made. “I couldn’t get it up over my hips,” Winfrey revealed, (via Access Hollywood). “So my hairdresser … had to lay me on the floor and push my butt down and zip and so I rode to the Oscars, really no exaggeration, planked in the back of a limousine.” What a way to arrive!

Emma Stone’s underwear shot

Emma Stone was really excited about her 2015 Oscar nomination for her performance in “Birdman.” In a statement to express her glee, Stone wrote: “Well this is surreal. I am completely knocked out. Thank you to the Academy for this incredible honor. I am very proud and lucky to be part of ‘Birdman’ and I can’t believe it came to this,” according to Vanity Fair. “I am so f***ing excited. Are you allowed to say ‘f***’ when making a statement for the Oscars? I’m just really f***ing excited,” she concluded.

While she was understandably excited, that excitement most likely turned into nerves at the event itself. A jittery Stone adjusted her gown on the red carpet and accidentally flashed her nude-tone underwear. The green Elie Saab gown she wore boasted a high slit, according to Express, so it makes sense that the innocent adjustment accidentally revealed a little more than the actor planned for. Thankfully, Stone didn’t seem to notice and kept walking. Good for her because she looked incredible.

Underwear seemed to be the topic of the evening, because when “Birdman” won for Best Director, Alejandro G. Iñárritu joked about his secret good luck charm during his acceptance speech. “Tonight, I am wearing the real Michael Keaton tighty-whities. … They are tight, smell [sic] likes balls, but it worked. I’m here. Thank you, Michael.”

Farrah Abraham at the Venice Film Festival

MTV alum Farrah Abraham, famous for appearing on “Teen Mom,” shocked viewers on the red carpet at the 2019 Venice Film Festival when she adjusted her gown and accidentally revealed she was sans underwear, People noted. Abraham wore a gown by designer Christophe Guillarme that featured a plunging neckline and a nearly hip-high slit. The slit appeared to be the problem, as Abraham moved it a little more than she may have bargained for, exposing herself.

However, Abraham didn’t deflect attention from the evening. She posted praise on Instagram following the screening for “Ad Astra,” and shared a photo of her gown (with the slit intact). “As an actress, writer, producer, Director I enjoyed it! Might be best this festival,” Abraham wrote in part. “I was grateful to see & meet fans in Venice Italy!” Abraham tagged the dress’s creator as well as her own jewelry line, Kollection.

Abraham has her own contentious history in other ways, regardless of red carpet accidents. She was let go by MTV from the “Teen Mom” franchise for pursuing a career in adult entertainment, per Us Weekly, and also got into some trouble with her fans when she had a photoshoot for her then-7-year-old daughter, Sophia, who wore makeup and bikinis. The photoshoot was later shared by her mom on social media. Abraham has certainly been through a lot of heat, so any press concerning a wardrobe malfunction would likely not faze her.

Giuliana Rancic stole the show thanks to her zipper

Beloved TV host Giuliana Rancic suffered a wardrobe malfunction on live TV at the 2014 Academy Awards. Like clockwork, Rancic had just been praising her dress’s designer, Paolo Sebastian, and its origins right before her zipper split open. “I’m all about Australian designers right now,” she said, according to the Daily Mail. “I feel princess-y — a girl deserves to feel like a princess once in a while.”

Shortly after, Rancic confessed on camera: “My zipper broke!” Adorably, Ryan Seacrest came running over to help Rancic fix it and joked, “Should someone be hosting?” Despite his best efforts, all he had on hand was tape. “This is what you brought to fix my zipper,” Rancic laughed. “Old tape?”

Obviously, the mishap hit the news, even way over in Australia. As far as the designer went, Paul Vasileff for Paolo Sebastian said to Confidential (via the Herald Sun): “I cannot believe that happened,” adding, “I hadn’t seen the dress for a month or so and its invisible zip so it’s a bit tricky, and they do tend to break.” The Australian-based team was delighted that Rancic chose to wear their design. “We just had ice cream for lunch to celebrate,” Vasileff added. “It’s an unfortunate thing to happen right then. She took it well but yeah, I will be calling and [apologizing].” Rancic certainly did take it well and while Seacrest didn’t do much, his effort was laudable.

Judy Greer left a trail of beads

In 2012, Judy Greer attended the Academy Awards because “The Descendants” was nominated for best writing (which it won) and best picture, among other nominations. Greer gave Vanity Fair an excerpt from her collection of essays, “I Don’t Know What You Know Me From: Confessions of a Co-Star” and joked that she had been in the movie for 13 minutes, but still attended the event.

While there, her dress betrayed her. “It was lent to me by the designer Monique Lhuillier, and it was pretty amazing,” Greer said of the garment. “It was tight, black, and altered to fit my every curve, and there are a lot. It had a thick stripe of silver beads down the front. Tiny little silver beads.”

Then things quickly went south. “Those f***ing beads started it all,” Greer wrote. “My very first step on the red carpet, someone stepped on the hem of my dress and the beads just started unraveling. Everywhere.” Greer went on to describe the horror show, writing that her publicist literally knelt on the red carpet in front of her to mend the dress in a futile attempt to keep some beads on. A-listers passed by Greer and her on-the-spot tailoring job as if nothing was happening. Greer herself played it cool, too. All photos of her that evening showed a composed, beautiful person (with a few less beads on her dress than originally), but she wrote she “was sobbing on the inside.”

Chrissy Teigen was a sight to behold

At the American Music Awards in 2016, Chrissy Teigen might not have accounted for the side view of her otherwise gorgeous dress. She wore a gown by Australian designer Yousef Akbar, reported Page Six, that boasted a slit so high it went right up to her rib cage. The whole contraption was held together by a safety pin and from the front, it looked stunning. While it also looked great from the side, that angle revealed that Teigen was without underwear.

Always hilarious on social media, she jumped on Instagram after the event to issue a faux mea culpa. “AMAs! love you so so so much,” adding, “(apologies to anyone harmed mentally or physically by my hooha).” Teigen then credited the designer, Akbar, Dsquared 2 for her shoes and, best of all, SEV Laser Aesthetics for her laser hair removal. No one could have spun a wardrobe malfunction so perfectly.

The designer, Akbar, certainly loved Teigan’s take. He told the Daily Mail that he was surprised and delighted to see Teigen wearing his dress. “When I woke up and checked the news, I actually had to keep looking at the dress for ten minutes as I thought someone else might have just designed a near-identical design,” he confessed, adding that Teigen was the perfect person for such a garment. “I don’t think there was a wardrobe malfunction, as you could hardly see anything! To me, Chrissy wore the creation perfectly,” he stated.

Lily-Rose Depp hung on for dear life

Lily-Rose Depp, daughter of Johnny Depp and Vanessa Paradis, had to hold her top together after it slipped down. She was attending the BFI London Film Festival in October 2019 when a strong wind ruffled her white top out of place, according to the International Business Times. Depp held her blouse in place and finished walking the red carpet.

Depp’s posture of privacy is one she practices in many areas of her life. The French-American actor told Vogue that she’s wary of social media, especially Instagram. “I’ve really stopped using it in a personal way,” she said of the site. “I never like revealing too much about myself. Once you start giving people that look into your life, then they just want more and more.”

Despite her need for privacy, Depp has already enjoyed a rather illustrious career for someone so young, made all the more successful because she can star in both French and English cinema. “I speak exclusively French with my French family, and exclusively English with my American family,” Depp told Keira Knightley for Interview. “So I feel very at home in both of them. I’ve always spoken French with my mom. That was important to her, and it’s important to me.” While tops may come undone and try to fly away, clearly Depp knows how to keep grounded and close to her international roots.

Jennifer Garner accidentally showed her shape wear

Jennifer Garner was walking the red carpet alongside Steve Carrell, her co-star in the 2014 film, “Alexander and the Terrible, Horrible, No Good, Very Bad Day,” when a gust of wind swooped up her little black dress, revealing her shape wear, per ET. While it was likely not something she intended to share with the public, Garner laughed and seemed to shrug it off like a champ.

This isn’t the only time Garner has addressed the function of shape wear, overtly or covertly, when it comes to walking red carpets. In 2016, she told Jimmy Fallon on “The Tonight Show” about how her black Versace gown for the 88th Academy Awards required a team and took the concept of shape wear to the next level. “See how I have a waist right there,” Garner said, pointing at a picture of herself in the dress. “I don’t have one in real life anymore.” Garner said she wore a metal corset and admitted, “My ribs were compressed.”

When Fallon asked if it was like a pair of Spanx, Garner was quick to correct him. “No dude! It’s not like that,” she said. “It’s so intense!” She said that during the evening, she had a muscle spasm because her ribs were so compressed. It legitimately sounded horrendous. The only plus we can think of is that, considering she was bolted into the outfit, no gust of wind was going to cause a wardrobe malfunction that night!

Katherine Heigl’s dress fell apart

Katherine Heigl had a legitimately awkward moment at the 2010 ShoWest Awards where she was awarded the Female Star of the Year, according to Us Weekly. The event was held at the Paris Las Vegas hotel and while she was on stage, in front of everyone, the strap on her red dress broke. Radio personality Billy Bush, who was hosting the event, stood behind Heigl and held her strap while she finished her acceptance speech, Reuters noted.

While the event was memorable, Heigl fell off the map soon afterward, thanks to some situations that painted her as a tough person to work with. Heigl spoke to The Washington Post in January 2021 to address her history. “I may have said a couple of things you didn’t like, but then that escalated to ‘she’s ungrateful,’ then that escalated to ‘she’s difficult,’ and that escalated to ‘she’s unprofessional,'” Heigl explained. “What is your definition of difficult? Somebody with an opinion that you don’t like?”

To be fair, the actor said that parts of the film “Knocked Up” came across as misogynistic and that she didn’t pick up an Emmy for her performance in “Grey’s Anatomy” because the writing wasn’t good enough. Ouch! Heigl said her subsequent experiences were equally tough. No matter how much she apologized, she couldn’t mend the bridges. However, she’s slowly carving her way back into Hollywood and we have a feeling her old wardrobe malfunction is likely low on her radar.

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