10 Celebrities Who Unfairly Found Themselves On The Worst-Dressed List

What is it about worst-dressed lists that compels us to keep reading them? Is it curiosity about what people consider terrible fashion? Is it the guilty pleasure of watching someone rich and beautiful get taken down a peg? Whatever the answer, the tradition has withstood the test of time. When actor-turned-designer Richard Blackwell published his first ranking of badly dressed women in 1960, he unwittingly discovered that teasing sold newspapers in a way that admiration never could. And he knew exactly what he was doing. "I merely said out loud what others were whispering," he once said, per CBS News. "It's not my intention to hurt the feelings of these people. It's to put down the clothing they're wearing."

Blackwell was seemingly just having a bit of fun with human nature and our impulse to keep score. Yet museums and auction houses don't bother with what the press said about a particular outfit. The gown that was called a joke is now behind some glass. The couture that was branded a mistake now hangs somewhere for all to see as a piece of history and art and culture. Even in recent years, we've had examples of the internet handing down a verdict only to take it back a few years later.

So perhaps it's time to see fashion police in a different light. Maybe it's entirely possible to ignore what the critics said the morning after and consider where the clothes actually ended up. In fact, it turns out that for particular cases of the worst-dressed celebrities in history, the list-makers lost badly enough that the outfits they tried to bury turned into trends everybody wished to copy. Here are ten stars whose supposed fashion crimes have aged well enough to embarrass everyone who laughed.

Princess Diana's taste was once called into question by fashion critics, and she even topped Richard Blackwell's worst-dressed list in 1982 (per Today). In 2025's "Dianaworld: An Obsession," writer Edward White says that when she was alive, " ... it was far from universally acknowledged that she had a flair for dressing" (per Marie Claire). Her Sloane Ranger style, including the printed sweaters, garnered a lot of less-than-favorable reviews. The red jumper she wore to a June 1981 polo match at Windsor adorned with rows of white sheep refused to die, and it saw a resurgence when a replica was showcased on "The Crown." In 2023, the original jumper sold for $1.143 million.

Cher's most iconic '80s outfits all had a shimmer to them, including the above look. After Cher was snubbed for her performance in "Mask" at the 58th Academy Awards in 1986, she got Bob Mackie to design her the infamous bikini-style two piece with a black beaded skirt. Today reported that Cher had been crowned in Richard Blackwell's list as the worst-dressed woman of 1984, and in 1991, he ranked her the worst-dressed woman of the previous thirty years (via UPI). Years later, she and her favorite designer got the last laugh — "The Cher Show" put all the looks back on the stage and Mackie ended up bagging a Tony Award for best costume design of a musical in 2019 for his work.

Demi Moore turned up at the 61st Academy Awards on March 29, 1989, in a black corset, black bike shorts, and a brocade half-skirt with a floral and gold pattern. There was no stylist behind this particular look, and Moore had put it together herself. As you'd expect, the industry treated it as a catastrophe. The trade paper Women's Wear Daily ran her on its front page and added the coverline: "Thank God, no designer is to blame." Looking at that outfit now, it feels less like a worst-dressed moment in Oscars history and more like, well, Tuesday. Corsets have become a staple for the closet of any fashion maven, and it looks like they're here to stay.

Taylor Swift co-chaired the Met Gala on May 2, 2016, and dressed for the event in a custom Louis Vuitton silver minidress with a snakeskin pattern and cutouts at the waist. It was complemented with strappy knee-high heels and a platinum cropped bob, an era later christened by her fans and media as "Bleachella." The 'fit has landed on worst-dressed lists and on lists ranking Swift's worst outfits from every era, but when you read the complaints, it's not usually about the dress itself, but how its different from what Swift usually wears. Years later, Mused from the Victoria and Albert Museum compiled the best Met Gala outfits and gave it a shoutout, and Business Insider put it at the top of their ranking of Swift's Met Gala looks from across the years.

Lady Gaga wore roughly 40 pounds of raw beef to the MTV Video Music Awards in 2010, and accepted Video of the Year in it. Now whether it was a terrible choice for a dress, fashion and, well, sanitation-wise, is a subjective matter, but the condemnation was immediate. PETA issued a statement the next day complaining that " ... there are more people who are upset by butchery than who are impressed by it ... " After the show, Gaga told Ellen DeGeneres that the idea carried "no disrespect" toward vegans and was instead a protest against the American military's treatment of gay soldiers under "don't ask, don't tell" (via Billboard). The Rock and Roll Hall of Fame later froze and dried the dress into jerky, then put it on display in June 2011 as part of "Women Who Rock: Vision, Passion, Power."

May 6, 2013 marked Kim Kardashian's first Met Gala appearance, and she attended as Kanye West's guest while heavily pregnant, in a high-necked, long-sleeved floral Givenchy gown by Riccardo Tisci. The internet decided to have a field day, with side-by-side memes comparing her with floral couches. Robin Williams tweeted a photo of himself in the flowered dress from "Mrs. Doubtfire" beside her, joking, "I think I wore it better!" (via The Hollywood Reporter). Kardashian later revealed to Vogue that she "was crying the whole way home," and said, "I know no one really probably wanted me there at the time." She's since come around on it, and by October 2023, a pregnant Kourtney Kardashian was recreating the gown as a Halloween costume.

On January 20, 1990, Julia Roberts arrived at the Golden Globes in a charcoal Armani suit that she'd bought from the menswear section of the label's Rodeo Drive store. She wore it with a white shirt and a floral tie, and the end result was something radical for the time. Per Today, Richard Blackwell named Roberts the worst-dressed woman of 1991, but more than thirty years on, the suit has turned into a reference point. The media has since revisited the look as a landmark rather than a misfire, putting it alongside Cher's showgirl outfit as one of the most defining looks in awards-show history.

Madonna repeatedly appeared on Richard Blackwell's worst-dressed list in the 1990s, topping 1992's list (via LA Times). When she opened her "Blonde Ambition" tour on April 13, 1990 in a pink satin corset with a cone-shaped bra by Jean Paul Gaultier, the condemnation was swift and brutal. Due to the sexual nature of the performance, Pope John Paul II urged to boycott the show, and a campaign forced the cancellation of a Rome date. But what happened next is that the world took notes. Underwear as outerwear went from scandal to one of the most popular trends in modern fashion. The corset was a highlight of "The Fashion World of Jean Paul Gaultier" exhibit around the world. Of all the fashion trends popularized by Madonna, few have proven as durable as this one.

Björk arrived at the 73rd Academy Awards in March 2001 in a Marjan Pejoski creation shaped like a swan. The dress was essentially a plush swan worn as a gown, and the reaction was not mixed. Joan Rivers, working the red carpet, said, "The girl should be put into an asylum" (per BBC). Stylist Steven Cojocaru derided it as well. It also earned a reputation for appearing on worst-dressed lists. In time, many institutions came around. Valentino reinterpreted the swan for its spring 2014 show, and the Museum of Modern Art showed the original in its 2015 Björk retrospective. Even after two decades, it remains one of the most memorable looks in Academy history.

When Rihanna was pulling up to the Met Gala on May 4, 2015, she was convinced that she looked like "a clown" in her sweeping yellow cape designed by the Beijing couturier Guo Pei (via Access Hollywood). The 55-pound embroidered silk took two years to make, and within an hour, the timeline had rendered its verdict and dubbed it anything between a pizza and a poured omelette. Unbeknownst to all, Pei would go on to join the Chambre Syndicale de la Haute Couture and make her Paris debut in January 2016. Years later, she attributed that recognition to Rihanna, claiming, "Rihanna gave the gown a second life" (per W Magazine).