The Worst Dressed Celebrities Of All Time

The rich and famous are expected to present themselves as idealized purveyors of everything chic on the red carpet. Because of this expectation, it can be jarring to see someone who possesses vast amounts of money but little style. For instance, a unique spin on the LBD or a statement piece is often more than enough to land a celeb in fashion critics' good books. But as the folks in this rundown prove, even the most tried and tested wardrobe staples can be styled to fail. Despite their designer labels, the only label these stars boast is worst dressed.

Ultimately, however, style is highly subjective and an extended expression of oneself. Though these celebrities have made the odd gaffe or two (or three, or four), their fits will still be considered a serve in someone's Insta feed. Moreover, many of the worst-dressed celebs have evolved throughout the years to refine their sartorial palate. As centenarian fashion icon Iris Apfel once said, "Fashion you can buy, but style you possess. The key to style is learning who you are, which takes years."

We're taught to admire the exclusive haute couture, but instead, we're left with a hawt mess. Let's find out who's committed crimes against fashion and who ought to have the (look)book thrown at them: Here are the worst-dressed celebrities of all time.

The Y2k aesthetic is steadily making a comeback, with Zellennials embracing all things aughts. But taking a look at Disney alum Ashley Tisdale's looks from the era, we can't help but feel perplexed by this resurgence. Throughout the 2000s, Tisdale was the queen of fashion faux pas. Her greatest mishits include wearing flared jeans under asymmetrical strappy dresses, camo paired with synthetic fur, and donning a Hello Kitty sleep mask as a hair accessory (as well as an assortment of beaded berets). "Everyone goes through an awkward stage," Tisdale confessed to Cape Cod Times in 2007.

Reflecting on her outfits in an interview with People in 2017, she explained that her stylist was the same person who dressed her character, Maddie Fitzpatrick, on "The Suite Life of Zack & Cody." However, she soon learned that she'd made a grievous error and ended up looking like Maddie for public appearances. "I wore this really weird pink camo skirt and this pink furry thing ... I said, 'Ooh, put me in it!'" she recalled of one outfit. "And instead of wearing it like you would normally wear it, I was like, 'I am going to do it have one of my arms out and have it going across my body.' It was the weirdest thing."

These days, Tisdale is able to reflect on and laugh at her fashion mishaps. However, her aesthetic is now back in style, so it seems her character had the last laugh after all.

Icelandic songstress Bjork has won praise and plaudits for her unique musical output, fusing electronica with Worldbeat. It stands to reason, then, that her fashion choices are similarly eclectic and uncompromising.

Nominated for Best Original Song for her performance in Lars von Trier's "Dancer in the Dark," the singer attended the 2001 Oscars in an unforgettable swan dress. The gown was designed by Marjan Pejoski and featured a stole in the shape of a swan's head and a layered skirt. Subsequently, she made Richard Blackwell's Worst Dressed List, with the critic declaring, "She dances in the dark – and dresses there, too." Ouch. But Pejoski thought that Bjork did the flamboyant design justice. "It was fantastic of her," Pejoski told Vogue. "So rebellious, at a traditional occasion like the Oscars. I respect tradition of course, but everybody and everything deserves to be laughed at from time to time."

The dress was by no means her sartorial swansong, however. She went on to wear a number of unusual fits at subsequent events, including dressing as a full-on butterfly at the 2015 Governors Ball Music Festival. Though her aesthetic may not be to everyone's liking, there's no denying that Bjork knows how to make a fashion statement. "They wrote about it like I was trying to wear a black Armani and got it wrong, like I was trying to fit in," Bjork told The New York Times of the now infamous swan dress. "Of course I wasn't trying to fit in!"

With a career spanning almost 60 years, it's understandable that Cher has suffered a few fashion misses. Speaking to The New Yorker, designer Bob Mackie said that he deliberately selected ostentatious looks for the icon. One example was the controversial semi-nude dress she wore on the cover of Time in 1975. "I didn't know it was going to cause such a hullabaloo," Mackie quipped.

Infamously, the star showed up to the 1986 Oscars wearing an enormous feather headdress, mesh sequined bra, and matching low-rise skirt that left little to the imagination. Although the outfit seemed little more than a campy concoction, there was a deeper meaning behind it. The star sought to make a mockery of the prestigious event in protest of the Academy's decision not to nominate her for the film "Mask." "I was really hurt," she told Film Comment in 1988, "and I know all the talk: they don't like the way I dress ... they think I'm too flamboyant, they don't think I'm serious. So then I decided I could go in a little black dress. And then I thought, well ... let me go and remind them what it was that they truly don't like about me."

In 1991, Richard Blackwell labeled Cher the worst-dressed woman of the last 30 years. "From toes to nose, she's the tacky tattooed terror of the 20th century," he declared. These fashion faux pas aside, there's no denying that Cher is adept at living up to her camp-forward image.

One would expect the President of the United States — and a successful businessman to boot — to conduct himself or herself professionally. But Donald Trump made numerous fashion blips during his presidency, some of which occurred during high-profile engagements.

During a meeting with Senator Tim Scott, for instance, he was widely criticized for his mismatched suit, pairing a navy jacket with black pants. And when meeting Queen Elizabeth II in 2019, he was lambasted for wearing a tiny ill-fitting dinner jacket. Despite the jacket being visibly tight on the then-POTUS, the sleeves appeared too long and baggy for his 6'2" frame. As The Cut put it, "Trump often looks like he's swimming in his clothes." Moreover, Esquire argued that his sorry suit was likely responsible for the queen's sullen countenance in official snaps. Undoubtedly, Trump was dressed to kill the vibes.

Throughout his premiership, he also made all manner of gaffes when picking out neckwear. According to Chris Christie's memoir "Let Me Finish," Trump often wears unusually long ties because he believes they have a slimming effect. But as GQ counters, this is a major sartorial misstep, since a tie should typically reach one's midsection and Trump's only falls several inches below his belt. Accordingly, Trump has frequently appeared on GQ's list of the worst-dressed men of the year. High Snobiety went as far as to brand him the worst-dressed president of all time.

There was a time when Paris Hilton reigned supreme as the queen of all things girly and garish. At the height of her It-girl sovereignty, she sported peak Y2K socialite garb, often with her micro-pooch poking out of a Louis Vuitton handbag.

The heiress' fits included extremely low-rise jeans that showed off her washboard stomach, fur vests with matching flared pants, and, of course, velour tracksuits. (We can thank Hilton for Juicy Couture becoming a staple of every Sweet 16 party of the aughts.) In 2003 she topped Richard Blackwell's Worst Dressed list, with the critic declaring, "From cyber disgrace to red carpet chills — she's the vapid Venus of Beverly Hills!" Three years later, she shared the No. 1 spot with Britney Spears.

But Hilton believes that her worst outfit of all time was a curious little number she showcased at Sundance in 2001. She wore a black and fuchsia Patricia Field tulle dress, paired with a white bomber jacket and red beanie. "It was the worst outfit I've ever worn in my life," she told Yahoo. Elaborating on the look in a chat with The Sunday Times, she explained that the frosty weather conditions contributed to the confluence of mismatched pieces. "I wore this pink tutu dress that I got at Patricia Field with moon boots and a beanie because it was so cold and nothing matched and it just looked beyond," she said. "You live and you learn."

Though his wife Victoria is a much-lauded fashionista and designer, David Beckham hasn't exactly been on point when it comes to keeping up appearances. On The Overlap, he dispelled claims that Victoria had been dressing him, explaining that he's always loved fashion (though it hasn't always loved him back). He was voted GQ's worst-dressed man of 2005, with designer Manolo Blahnik lamenting, "[He's] the original fashion victim."

One of Becks' most widely derided outfits was a twinning moment with Posh from 1999, in which the couple donned matching leather jumpsuits. To this day, Victoria says the look haunts her. Meanwhile, addressing the infamous fit on "The Late Late Show with James Corden," her husband insisted that the leathery gaffe wasn't his idea. Still, Becks has no regrets. "They were right at the time," he said. "The leather outfit ... it could have been a lot worse on that evening. Because we were walking out the door and I was like, 'Why don't we get a motorbike?'"

A year earlier, he was widely lambasted for wearing a sarong, an outfit Ali G dubbed "so wrong." But as the BBC argues, this mockery was largely the product of Britain's macho lad culture. Undoubtedly, Beckham walked so Harry Styles could run with his on and off-stage fashion. "Twenty years ago when I wore that sarong, people were shocked," he told The Telegraph. "It was an outrage ... Today no-one bats an eyelid if a guy wears a sarong in the street."

Kim Kardashian is many things: Reality TV star, entrepreneur, and savvy girl boss. But when it comes to serving lewks, Kim K hasn't always delivered the goods. In a chat with E!, she poked fun at her fashion mistakes. She particularly regrets her much-maligned Y2K looks, including an infamous triple Fendi fit from 2006, which she deems one of her worst outfits ever. "I thought I was killing it," she quipped. Unfortunately, these slip-ups weren't confined to the 2000s.

In a 2014 poll by Mail Online, readers were asked to vote for Kardashian's biggest fashion fails. Among the ensembles that made the cut were a nude latex dress that hugged Kim's curves, a double denim coordinate paired with pink heels, and a hole-adorned pantsuit that looked like it had served as a blanket for a litter of kittens. At the number one spot was a floral maternity gown worn at the 2013 Met Gala. "I have to say that considering Kim Kardashian probably has so many personal stylists, she never seems to get it right," said one pollster. "That floral dress she wore to the Met Gala was absolutely awful. She actually looked like the sofa I have in my living room."

The oversights continued into the next decade. Appearing at Paris Fashion Week in 2023, Kardashian was dragged for wearing a camo-print sports bra and coordinated pants, complete with a faux fur fanny pack. "Why is Kim wearing a Minecraft grass block top?" tweeted one confused observer.

Jared Leto may have been blessed with a Benjamin Button-esque ability to perennially postpone the aging process, but his sense of style has not stood the test of time. In 2011, GQ hailed him the worst-dressed man in the world, arguing that the actor had turned terrible fashion choices into an art form. His greatest hits include a wolf-eared trapper hat paired with an otherwise chic monochrome ensemble, harem pants under a boxy overcoat, and a bright red suit complete with serial killer-style black gloves.

He continued to make it onto worst-dressed lists in the years that followed. In 2016, he was lampooned for his Frankenstein's monster of an outfit at the Fashion Awards, sporting a kimono over a mismatched tux and committing a cardinal sartorial sin: Wearing white socks with black loafers.

The actor went the extra mile at the 2023 Met Gala by dressing as Karl Lagerfeld's beloved cat, Choupette. Some celebs gave Leto the side-eye for the uncomfortable ensemble. "Jared Leto showed up as a furry," Nick Jonas told Vogue. Meanwhile, others argued that he was cosplaying rather than showcasing a look befitting the prestigious event. "[Leto] was really pushing it," Joshua Balster, the outfit's project manager, told The Guardian. "He wanted it to be like a real cat." After all these blips, one can't help but wonder if Leto has any style regrets. "I'm sure if I take a trip down memory lane there may be a few things I regret," he told GQ.

Julia Fox is known for her rather eclectic approach to styling. The actor has worn upcycled jeans fashioned into a dress and exhibited her love of latex via barely-there belly tops, thigh-high boots, and matching oversized gloves. And after wearing a cut-out LBD, which exposed one half of her bra and thigh, at the 2022 Independent Spirit Awards, she topped the Daily Mail's worst-dressed list.

Matters weren't helped by her brief rendezvous with Kanye West, with the rapper seemingly being responsible for Fox's next fashion mishaps. Speaking to Interview Magazine, she revealed that West surprised her after their second date with a hotel suite full of new clothes. "It was every girl's dream come true," she said. "It felt like a real Cinderella moment. I don't know how he did it, or how he got all of it there in time. But I was so surprised."

A Cinderella story it may have seemed, but her dream soon turned into a nightmare. At Paris Fashion Week in 2022, the couple pulled a Britney Spears and Justin Timberlake by donning double denim. The outfits were much memed, with detractors taking to Twitter to throw shade at Fox's stylistic transition, courtesy of her then-beau. "This whole Kanye West x Julia Fox thing is so funny," tweeted one amused observer. "She literally looks like those mom/child duos when the mom dresses them how they want and the kid gets no say."

Adam Sandler has made a career out of playing manchildren stuck in a perpetual state of arrested development. Behind the scenes, art imitates life (when it comes to the funnyman's wardrobe, at least). Sandler is known for drowning himself in baggy garb on the red carpet, often in marked contrast to his stylish co-stars. At the premiere of "Murder Mystery 2," for instance, Jennifer Aniston donned a sparky designer dress and chic stilettos, while Sandler showed up in a Knicks hoodie, khakis, and sneakers. Suffice it to say, Aniston was not impressed. "What the hell are you doing?!" she remarked to her co-star during a red carpet chat with Entertainment Tonight. "I'm not standing next to him. Sweatpants ... I said, 'Please don't wear your sweatshirt.'"

This certainly wasn't the first time Sandler rolled out of bed and straight onto the red carpet. In fact, the comedic actor is seldom seen in a suit, favoring oversized casual attire. "I feel terrible," he confessed on "Jimmy Kimmel Live." "I wish I could dress better. I have the clothes ... My wife went out and got me a bunch of stuff. It's just a little too small. I'm just in such a bad mood when it's tight."

Though his style is unconventional for an A-list actor, Sandler has been praised for operating in full-on goblin mode long before it entered the cultural lexicon. In 2021, Vogue called him "the unofficial ambassador of pandemic style," lauding his commitment to comfort.

Bai Ling first found Hollywood fame thanks to the 1994 cult classic "The Crow," in which she arguably set the archetype for the Hot Goth GF meme. Since then, she's sported innumerable risky and risqué looks on the red carpet, such as pairing a pink tutu with a fur scarf and utilizing a dragon as a stole. Her fashion choices have divided critics, with some branding her as one of the worst-dressed stars of all time and others commending her daring approach to celeb style.

In a 2004 interview with Observer, she addressed her often outrageous outfits, claiming that she has eight different stylistic personas within her collaborating on her fashion choices. "One of the girls is a party girl. She's like, 'Let's go party!'" Ling explained. "I say, 'No, no, no, I'm tired.' She says, 'Let's go party!' The party girl's very stylish, weird."

In 2015, the age-defying star wore what some critics deemed her worst outfit yet, consisting of a tiny bra and a sign for a skirt that read, "Bai Ling's Cookie: Film Proposes: Will You Marry me? Fashion Says: YES!!!" Chatting to Vice the following year, Ling said that she couldn't give a hoot if fashionistas don't dig her style. "I am authentic," she declared. "I don't care what's the trend. If I'm going to wear this out tonight then that's my red carpet dress."

Having been the quintessential '90s pinup boy, Johnny Depp's style is reminiscent of someone stuck in the past, with wannabe rocker vibes to boot. Though acclaimed as an actor, Depp isn't exactly a fashion icon. The erstwhile Captain Jack Sparrow is famed for his penchant for wearing scarves (indoors) and sunglasses (indoors), as well as copious amounts of jewelry. His aesthetic is so notorious that it prompted The Onion to pen an article entitled, "Johnny Depp Now Completely Made Of Scarves And Bracelets."

In 2013, he made it onto GQ's dreaded worst-dressed list, with the outlet calling out his uncanny ability to simultaneously both under and over-dress for any occasion. Although many of his worst outfits were captured by the paps when Depp was out and about running errands, his red carpet style is just as calamitous. In 2015, the star was called out for sporting an ill-fitting suit paired with suede creepers and myriad mismatched necklaces at the "Black Mass" premiere. This was in stark contrast to his then-wife Amber Heard, who wore an immaculate LBD and chic red heels.

However, Depp himself is the first to admit that he isn't great at outfit coordination. Appearing at the Beauty Awards in 2016, he argued that his grooming habits make up for his absence of style. "When I met people they said, 'You do look like a hobo, but you smell really good,'" he remarked. "And goddamn it, I smell really good!"