The Biggest Celebrity Fashion Misfires

Celebs have access to the greatest clothing brands and fashion designers in the world. Whether it's running to the grocery store in Christian Louboutin heels or wearing a one-of-a-kind couture dress on the red carpet, the biggest stars are always wearing the most exquisite pieces. Or so you would think. Thanks to photos and memes, some terrible outfits live on forever. And over the course of a career, a celeb is bound to strike out at least once in the fashion department.

Sometimes, a look that is so bad turns out to actually be legendary. Remember Björk at the Academy Awards in 2001? The Icelandic singer's "swan dress is probably the most iconic on the list of worst dressed," Marie Claire recounted, noting that this "look was designed by Macedonian designer Marjan Pejoski." And yet, people could not stop talking about the swan. In fact, in 2005, the dress "was auctioned off for $9,500," and Italian couture house Valentino created its own tribute to the "swan ensemble in its spring 2014 couture fashion show." 

In less iconic moments, though, some looks are just downright cringe-worthy. What's your worst outfit ever? It's time to remember the biggest celebrity fashion misfires.

One cold day, Lenny Kravitz, the ageless rocker, picked an accessory that may turn out to haunt him forever. In 2012, Kravitz left the house for a few errands with a knit beanie, aviators, and "essentially, a rug around his neck," GQ recounted. 

"I live in the Bahamas," Kravitz explained on The Tonight Show Starring Jimmy Fallon years later. "I'm used to hot weather, and I had to go to the store. I was buying some groceries ... I thought I'd put on a little scarf to protect my throat, and that's the scarf I had." The accessory ruined an otherwise perfectly fine outfit with slinky suede boots, brown leather jacket, and a shirt with Southwestern vibes. "The guy who made that scarf, who you can blame that on, he made that scarf and he gave it to me. And that was the day I thought I would break it out. And I had no idea that there would be paparazzi," Kravitz revealed about that fateful day.

After all the teasing, did Kravitz keep the meme-able scarf? "Oh yeah, absolutely," he admitted to GQ in October 2020. While the scarf photos have taken a life of their own, sometimes "three times bigger than it really is," Kravitz still sees the humor in the whole scenario. Especially for Halloween costumes. "People either do the Lenny Kravitz look — the onstage look — or they do the scarf," he said.

Sure, shorts might be the best clothing in the heat of the summer. But as president of the United States, it's not exactly an option to be seen in public without a dignified look. So, what's the presidential equivalent of a comfortable outfit come summertime? For former President Barack Obama, he decided to mix up his normal routine of dark blue suits with a lighter hue. 

During a 2014 White House press briefing on Syria and foreign policy, Obama approached the lectern with a very stylish tan suit. Little did he know that this choice of color would cause a crazy amount of controversy. "No One Heard Anything Obama Just Said Because His Tan Suit Was So Loud," read the subsequent headline of The Atlantic. The publication declared that Obama "debuted one of the ugliest suits in the history of this great nation."

The president's press secretary, Josh Earnest, even went on record the next day to further explain Obama's suit decision. "The president stands squarely behind the decision that he made yesterday to wear his summer suit at yesterday's news conference," Earnest said (via MR PORTER). "It's the Thursday before Labor Day, he feels pretty good about it." Looking back, it's amazing how a custom, khaki suit became one of the biggest scandals that rocked the White House.

Actors Billy Bob Thornton and Angelina Jolie first met on the set of the 1999 film, Pushing Tin, Entertainment Weekly notes. And their onscreen marriage ultimately turned into true romance when "they were married from 2000 to 2003," per Us Weekly. According to Thornton, the pair didn't last because each partner "just had different lifestyles." 

Perhaps the most memorable thing about their marriage is a peculiar display of affection. And no, we're not talking about PDA. Jolie and Thornton reportedly kept vials of each other's blood and wore them on necklaces. Thornton explained that the bizarre accessory seemed innocent enough, but was blown out of proportion. Speaking with Us Weekly, he remembered the conversation with Jolie was essentially, "Hey, let's poke our finger with a pin and smear a little on there, and when we're away from each other, we'll wear the necklace." However, once the press caught wind and retold the story, he added, "It sounded like we were wearing a bucket of blood around our necks."

Jolie told a similar story to Entertainment Weekly years after separating from Thornton. "It was never a vial anyway," she revealed (via Us Weekly). The actress further explained, "It was like a flower press. It was like from a slight cut on your finger and you press your fingerprint in. It was kind of a sweet gesture. I thought it was kind of romantic!" Romantic or creepy? We'll let you decide.

Perhaps the most famous family in Hollywood, the Kardashian-Jenners once showed "a proclivity for wearing vintage t-shirts," according to W magazine. Kylie and Kendall Jenner decided to capitalize off the trend and just create modern replicas of used gear. The sisters launched a "vintage tee collection" in 2017 "under their namesake brand, Kendall + Kylie." 

As recapped by Marie Claire, the collection featured their "faces superimposed over music stars like Tupac Shakur and The Notorious B.I.G." But the two apparently never received permission to use the photos of the famous rappers. "The Jenner sisters also faced backlash and accusations of cultural appropriation, with even Biggie's mom Voletta Wallace addressing the controversy," the article detailed. As Wallace posted on Instagram, "I have no idea why they feel they can exploit the deaths of 2pac and my Son Christopher to sell a t-shirt."

The ladies dropped the controversial t-shirts, and Kendall posted an explanation on Twitter in the face of much backlash. Apologizing "to anyone that has been upset and/or offended, especially to the families of the artists," she added, "We are huge fans of their music and it was not our intention to disrespect these cultural icons."

As the first lady of the United States, all of Melania Trump's outfits receive high press coverage. Her stylist, Hervé Pierre, shops for many of her outfits. "I go to Bergdorf, I go to Saks, Michael Kors, Dior," he told The New York Times. Another added pressure is to make sure her pieces are unique to avoid any controversy. Pierre said that while shopping, "I always ask: 'Was it already on the red carpet? Did somebody already wear it?' Because I don't want her to be on the 'Who Wore It Better' list." 

However, Trump's most controversial fashion choice didn't involve a "Who Wore It Better" debate, but rather a green jacket. As the former model boarded a plane in Washington D.C. to visit Texas in 2018, photographers captured the white text painted on the back of her coat. "I really don't care. Do U?" read the coat, per The New York Times. Since Trump was visiting children at a border detainment center, the fashion choice naturally caused major controversy.

President Donald Trump claimed on Twitter that the message on the olive-colored jacket "refers to the Fake News Media. Melania has learned how dishonest they are, and she truly no longer cares!" Meanwhile, Melania told ABC News that she wore the coat "for the people and for the left-wing media who are criticizing me. And I want to show them that I don't care."

After a successful and influential solo career as a combination rapper and producer, Kanye West started to branch out into fashion, especially his Yeezy line. Outside of his popular shoe empire, West's choice of fashion accessory in 2018 caused a different kind of reception. The artist proudly wore the same red hat that many of Donald Trump's supporters do, featuring the campaign slogan, "Make America Great Again." 

It marked West's biggest political statement since his scandalous comments about President George W. Bush. After a meeting together in Trump Tower, as recounted by The Washington Post, President Trump claimed in reference to West, "We've been friends for a long time." Perhaps unsurprisingly, this all resulted in major backlash — but it didn't end there.

Back in 2015, West announced at the MTV VMAs that he would run for president in 2020, and stayed true to this word when he put his name in the discussion for election. West told Forbes in 2020 that he no longer supported President Trump, noting, "I am taking the red hat off." One day after the Forbes interview, Trump said he supported the decision, claiming that West "is always going to be with us." But much like his choice to wear a MAGA hat, celebrities were shocked at the rapper's decision to run for president. And despite the objection and long shot at winning, West still seriously pushed his candidacy.

For the 2004 Super Bowl halftime show, the stunning Janet Jackson and Justin Timberlake performed side-by-side for the closing number, "Rock Your Body," SB Nation recapped. The two were familiar with each other since Timberlake performed with *NSYNC as the opening act for Jackson's 1998 tour. And Jackson featured on the song "(And She Said) Take Me Now" on JT's debut solo album, Justified. 

Despite the personal history, the two created even more history at the end of the Super Bowl performance. "Timberlake pulled off part of Jackson's outfit, briefly exposing her right breast in front of a TV audience of 140 million viewers," USA Today summarized. Thus started what the press referred to as "Nipplegate" — a debate over how this happened and who was responsible. Michael Powell, the FCC chairman at the time, said, "I think we were relatively convinced that somehow those producing the show knew what was going to happen.” But the producers claimed "they had absolutely no idea on how the artists just did this up on their own." After the incident, Timberlake alleged it was caused by a "wardrobe malfunction," which turned into a popular pop culture phrase, per USA Today. 

However, it was Jackson who unfairly took most of the blame for the incident. The singer was "not allowed to attend the Grammy Awards the following month, while Timberlake was not only allowed to attend, he was asked to perform," SB Nation reported.

Outside of the royal family, the most famous couple in Britain might be David and Victoria Beckham. The two met in 1997, when Victoria, then a member of the Spice Girls, attended one of David's soccer games. In the players' lounge after the game, a shy David remembered in a W magazine interview, "I just sort of waved from the other side of the bar." One week later, Victoria attended another game, "and this time he didn't let her get away, asking her for her phone number, which she jotted down on a plane ticket," the outlet noted. 

The next day, the soccer star reportedly drove from Manchester to London to see the singer. By 1999, the couple had their child and were married. And while the year was a complete highlight for their relationship, it also featured one of the lowest points in their fashion career. At a 1999 Gucci show, David and Victoria decided to wear matching outfits. Specifically, all-black leather. David told People that he and Victoria both lived with Victoria's mother and had separate rooms. After getting ready, "We both came to the kitchen and were like 'Wow.' It was A LOT of leather." 

David lightheartedly admitted that he and Victoria look back and wonder, "What were we thinking?!" However, he also confessed, "We still have those outfits."

Two of the biggest stars in '90s pop music, Britney Spears and Justin Timberlake delighted the world when they started dating. The pairing lasted from 1999 to 2002, according to Billboard. And in those few short years, they rocked some truly bad outfits. For example, this 2001 photo of the super couple in New York City to celebrate the release of Spears' third studio album, Britney. Both are wearing nearly every color in the tan spectrum: Timberlake looks like a poorly dressed Indiana Jones in a shiny leather jacket and khaki pants with brown stripes down the side, while Spears' fur-trimmed coat paired with suede cowboy boots are equally cringe-worthy. 

Looking back at his style choices, Timberlake said he had more important things on his mind. "Look man, you do a lot of things when you're young and in love, man. That's what you do," he told his former bandmate, Lance Bass, on The Daily Popcast. But it still doesn't compare to the couple's most famous fashion choice. At the 2001 American Music Awards, they showed up in matching, all-denim outfits. Spears wore a patchwork denim, floor-length dress, while Timberlake donned patchwork jeans and denim blazer — complete with a Levi's chest pocket and a denim cowboy hat. 

This denim nightmare hit legendary status and stars have continued to reference the iconic look — like when Katy Perry wore what Spears called an "amazing" and notably similar denim dress at the MTV VMAs in 2014, per E!.

As a young actress from England, Sophie Turner auditioned for Game of Thrones thanks to her drama teacher. Turner's role as Sansa Stark turned her into an international celebrity and led to her marriage with boy band heartthrob Joe Jonas. The couple welcomed their first child, Willa, in July 2020, per Hollywood Life.

As for style, Turner is a Louis Vuitton ambassador, Teen Vogue reported. But even with the big name sponsorship, she's still guilty of a few fashion missteps. Turner considered her outfit at "Kit Harington and Rose Leslie's wedding as one of her 'worst looks' of all time,'" according to the outlet. At the event, the actress wore a "fire engine red Louis Vuitton blazer dress, which she paired with a black-and-white checkered bag and thigh-high black boots."

Perhaps even worse for Turner was her outfit at a 2019 fan event in support of X-Men: Dark Phoenix. The actress, who plays Jean Grey in the film, showed how one decision may just ruin an outfit: She wore a sleeveless crop top with cool metallic trim paired with metallic pointed heels — very appropriate for the superhero theme. But for reasons unknown, Turner also wore high-waisted, mom-style jeans in a light wash with stripes down the side. The jeans seemed to clash with the rest of the look, and while some felt the bold fashion choice was "unexpectedly cool," we can't help but ask: Is the "X" she's making with her arms for X-Men or is Turner canceling her own outfit?

In October 2007, siblings Kourtney, Kim, Khloé, and Rob Kardashian dressed up alongside the family matriarch, Kris Jenner, for a celebration in West Hollywood. The occasion? The premiere of the new reality show called Keeping Up with the Kardashians. Here, Kim — alongside choreographer Robin Antin and former stepfather Caitlyn Jenner — dressed up to mark what would become the pivotal series in her career. But even with all the nostalgia from such a momentous occasion, and the family's fashion trendsetting ways, Kim still cringes when looking back at her outfit for the night. 

"I probably borrowed this dress at DASH, kept the tag on or just re-tagged it, and then returned it afterwards," she remembered in an interview with ET. Kardashian matched the crimson, low-V cut dress with a bright red lipstick. "I thought I made it. I don't know why I did the lip and the eye and the hair and the dress and the jewels and the French-tip nails," the celeb added. "Obviously it's cringe-worthy but I still respect it," the most famous of the Kardashian sisters said lightheartedly, noting that she fondly thought, "I was so cute," but also confessed, "I was so clueless." Kim ultimately declared, "This was probably one of the worst looks of my life."

Wealthy socialite Paris Hilton received a special package in the early 2000s from her friend, and inside were "velour two-pieces" by the brand Juicy Couture, per Vogue. "As soon as I put on my first Juicy tracksuit, I was obsessed," Hilton told the fashion magazine in a 2019 interview. "... I just fell in love with the brand, and it basically became my uniform," she remembered, noting that she started wearing the two-pieces all around town. For example, here at the 2004 NBA All-Star Game with then-boyfriend Nick Carter of Backstreet Boys (above, left), both wore matching wrist sweatbands. How cute.

Hilton explained that she stayed true with the fashion of the era. Or in her own words, "I think it was just all about being super extra." Take for example, this look from a 2004 party at The Beverly Hills Hotel (above, right): Hilton's green, jungle-print jacket with a fuchsia satin lining over a multi-purple colored fringe dress, plus a sky-blue satin bow tied around her waist, paired with a fuzzy blue purse. Combined, it created a true sensory overload.

But Hilton does have at least one fashion regret, recalling to Yahoo! Life a dress she once wore to the Sundance film festival. "It was a black corset and the bottom was hot pink tulle. But you couldn't wear heels because it was snowing, so I had snow boots," she said, recounting the look from the early aughts. "It was the worst outfit I've ever worn in my life," Hilton confessed.