10 Of The Worst Outfits In Oscars History That Totally Missed The Mark

As much as everyone loves to watch the Oscars every year to see whether or not their favorite actors are going to win, it's also about the fashion. Since the very first televised Academy Awards ceremony in March 1953, people have been tuning in to see what the Hollywood elite is wearing. While it's always fun to see someone you admire wear a stunning, haute-couture gown that fits them flawlessly, there's also a bit of delight in seeing some celebrities just absolutely fail in the fashion department. Whether it's a case of schadenfreude or simply seeing the rich and famous be kicked off the pedestal we put them on, there's something magical about the worst outfits at any award ceremony — especially the Oscars.

As we prepare for the 2026 Oscars, while wondering if Jennifer Lawrence will be showing some serious leg on the red carpet again this year, it's the perfect time to revisit some of the worst Oscar outfits in history. Or, rather the ones that landed on the worst-dressed lists the most. Once upon a time, in what feels like a galaxy faraway, Icelandic singer and actress Björk wore this now-iconic swan dress to the 73rd Academy Awards in March 2001 and it was immediately dragged by critics. Now, though, it actually pales in comparison to so many other looks. If anything, this dress, designed by Marjan Pejoski, was ahead of its time and quite avant-garde — something that can't be said for some of the following Oscar ensembles.

In 1989, Demi Moore did something that very, very few celebrities do when attending an award show: she wore something of her own creation. As one of the highest paid actresses of the time, meaning she probably had designers banging on her door and begging to dress her for the Oscars, Moore decided to wear a pair of spandex bike shorts, a velvet corset, and a gold metallic fabric at the waist for a train. Not only was it critically panned by the media, but WWD wrote at the time, "Thank God, no designer is to blame," declaring it an "Oscar Fright." These days, Moore is proving that red carpet style gets better with age.

When costume designer Lizzy Gardiner arrived at the 67th annual Academy Awards in March 1995, having been nominated for her work on "The Adventures of Priscilla, Queen of the Desert," she took the unconventional route. When asked about her dress of 254 expired American Express Gold cards, Gardiner told reporters, "I'm broke, and I didn't have anything to wear," according to CNN. While critics were divided on the statement that Gardiner may have been trying to make, in a 2017 interview with ABC News, the designer explained the dress may have upset so many people because she wasn't taking the event as seriously as she should have. Either way, Gardiner took home the Oscar that night.

When Jennifer Connelly attended the 2002 Academy Awards, she had been nominated for her performance in "A Beautiful Mind." While one would think that being nominated for an Oscar would inspire a glamorous look, Connelly went in the opposite direction; she wore a tiered, strapless dress and mismatched scarf that looked like something you'd wear to a garden party that you're not even interested in going to. As former Cosmopolitan and Woman's Journal Editor Marcelle d'Argy Smith wrote at the time regarding Connelly's outfit, the dress was a "shrieking beige" and the scarf was the color of "pale dung" (via BBC News). Connelly may be one of the most beautiful women, but not even she could save this Balenciaga dress.

As we already know, the early 1990s was a cruel time for fashion. Granted, it wasn't as bad as the trends of the 1970s that we hope never come back, but there was definitely a rough patch in there. Proof of this can be found in white high-low minidress that Geena Davis wore to the 1992 Oscars. Designed by Ruth Meyers and Bill Hargate, the dress didn't garner any fans — except for Davis, of course. "I was surprised," Davis told US Weekly in April 2025, referring to how she felt about the amount of hate the dress got at the time. It had been designed specifically for her, and she loved it. Davis even considered wearing it to the Oscars again as a middle finger to critics.

When Gwyneth Paltrow attended the 2002 Oscars in a gorgeous dress by Alexander McQueen, it wasn't the design that got Paltrow on the worst-dressed list, but how she wore it. Yes, we're still learning how to ace the sheer clothing trend, finding the sweet spot of how much skin to show. However, in 2002, even a glimpse of someone's nipple was an all-out scandal — which was Paltrow's first mistake. The second error she made was not wearing a bra; the bodice of the dress was not designed for anyone, of any breast size, to go braless. "I should have worn a bra and I should have just had simple beachy hair and less makeup," Paltrow said in GOOP Q&A in 2013, via Today.

When it comes to Cher, one of the most beloved celebs who's confronting aging with confidence, it's hard to decide if her outfits belong on the worst- or best-dressed lists; frankly, they can go in either direction. However, when Cher wasn't nominated for her performance in "Mask" at the 1986 Oscars, she was out for revenge and wanted people to know she was angry. Bob Mackie, who has been dressing Cher for decades, spilled the tea to The New Yorker in 2018. "There were a lot of people who said, 'That's not fashion!' And I said, 'Of course it's not fashion. It's a crazy getup for attention.' And it did get attention — people talk about it still," he said.

As much as we love Whoopi Goldberg, being fashionable isn't her strong suit. Not only did she make our list of worst-dressed attendees at the 2025 Oscars, but she was just as unfashionable over 30 years ago. Like anyone attending the Oscars, Goldberg had put quite a bit of thought into what she'd be donning for the 1993 ceremony: a lime green and purple satin jumpsuit with a bolero jacket. But as much as Goldberg adored the Lucille Ball-inspired ensemble, the media was relentless. "It hurt my feelings, I'm not going to lie," Goldberg said in October 2023 at the Fashion Group International Night of Stars gala, via People. "It kept me from dressing up for a very long time."

When Celine Dion attended the Oscars in 1999, thanks to all the hoopla surrounding "Titanic" that was released just two years before, it's safe to say she was probably feeling really good about herself. So good, in fact, that she thought a white John Galliano tuxedo, worn backwards — along with a hat that mostly covered her face — was a good idea. It wasn't. The look ended up on many worst-dressed lists because it begs the question: Why did anyone let this happen? In 2017, Dion defended the look to People, pointing out that no one was wearing pants to the Oscars in those days. However, this list proves otherwise. After all, we have Demi Moore in biker shorts in 1989.

Another award-winning actress showing up to the Oscars in an outfit they designed themselves? You better believe it. In 1990, Kim Basinger took a dress she'd created onto the red carpet, and now we're all stuck with the image forever. Part ball gown, part blazer, and an opera glove on one arm, this ensemble is so all over the place, and no one knew what to make of it. In February 2023, Basinger took to Instagram to gush about the dress, writing in the caption, "Inspired by Grace Kelly... I decided to put my own twist on it ... Down one sleeve, I chose to have the words 'To Russia With Love' — written in Russian! — in gold sequins... A nod to the James Bond film."

If there's anything to take away from this list, it's that the 2002 Oscars was a very strange night. Because of that, it only makes sense that we finish off with this doozy of dress by Versace, of all designers, that Faith Hill wore. Granted, Hill sang "Somewhere Over the Rainbow" at the ceremony that night, but she didn't need to dress the part. Or, if she did want to pay an homage to rainbows with her gown, she could have gone in a direction that looked less like she was going to hit up prom after the Oscars wrapped.