The Worst-Dressed Celebs In Oscars History

The Academy Awards ceremony isn't just about cinematic excellence; it's also the ultimate stage for Hollywood's A-listers to showcase their style. Every year, millions tune in not just for the winners' speeches and tear-jerking moments but also for the jaw-dropping, awe-inspiring looks gracing the red carpet — the very same looks that often become the fashion trends you'll want to copy as soon as possible. However, as we know, not every style moment can be a win, and not everyone makes the Oscars best-dressed list. In fact, amidst the glitz and glamour of Hollywood's most prestigious night are some unforgettable fashion faux pas that have left us cringing and questioning the decisions made by our favorite celebrities.

Despite the meticulous planning and the army of stylists at their disposal, even the biggest names in showbiz can miss the mark when it comes to dressing for the Oscars. From completely mismatched ensembles to questionable fabric choices, each year brings a handful of red carpet woes that become the talk of the town long after the ceremony has ended. And here are some of our favorite Oscar fashion fails.

In 2020, Kristen Wiig's red carpet moment at the Academy Awards turned heads for all the wrong reasons. Sporting a vibrant Valentino gown, Wiig's choice left us (and many others) scratching our heads. The dress, with its peculiar silhouette, quickly drew comparisons to lasagna on social media — not exactly the flattering comparison one hopes for at Hollywood's biggest night. The mesh detailing on the side was also an odd choice, and the star's mismatched pairing of nude shoes and black gloves failed to salvage the look.

Lady Gaga, a fashion icon known for always pushing boundaries, took a misstep at the 2015 Oscars. The star decided to go with a stunning Azzedine Alaïa dress, which would have been perfect had she not gone for the now-infamous accessory choice: red gloves. The addition of gloves simply distracted from the glamour of the dress, leaving fans puzzled by the mismatched pairing. Then again, the star is known for making odd and unpredictable fashion statements — after all, who could forget Lady Gaga's meat dress — but this Oscars look certainly resulted in numerous cleaning gloves memes.

If you ask us, Hilary Swank's 2003 Academy Awards ensemble by Christian Dior definitely missed the mark, as it gave high school prom instead of an Oscar-winning diva. Everything, from the light pink underdress with gems to the see-through pink chiffon layer, just wasn't right. In fact, the look was almost veering into costume territory rather than red-carpet sophistication. Swank's attempt at whimsy pink goddess fell short, highlighting the fine line between couture and costume on Hollywood's most glamorous night.

In 2007, Jennifer Hudson showed up to the Oscars red carpet in a gown by Oscar de la Renta, but it was accessories that ended up ruining the look. Despite the Y2K fashion trend and boleros being trendy at the time, this look failed to stand the test of time. "Jennifer was kind of sponsored by Talley and Vogue," a source revealed (via MTV). "Andre [Talley, Vogue's editor-at-large] insisted she wear that hideous Oscar de la Renta dress with the awful, awful gold python bolero. Jennifer really didn't want to ..." The clash between the shiny metallic bolero and her elegant jewelry took the attention away from what could have been a good look. In fact, removing the bolero later in the night significantly improved her outfit.

Jennifer Connelly graced the 2002 Oscars red carpet in a dress that was certainly too boring and casual for the event. The ruching detail on the gown gave off an unfinished appearance, which was accentuated even more by an ill-matched skinny scarf in a slightly different hue. Frankly, it seemed like this was a last-minute look, and that is definitely not a vibe you want to give off at the Academy Awards.

Sarah Paulson's appearance at the 2019 Academy Awards stirred mixed reactions as she opted for a very bold silhouette courtesy of designer Brandon Maxwell. While the voluminous skirt was undoubtedly an elegant choice, the matching top half of the ensemble left much to be desired. The stiff and bulky fabric, coupled with odd waist cutouts, overshadowed the skirt's potential, leaving Paulson somewhat lost in the dress. Despite the captivating color, this red carpet moment didn't give us much.

Mariah Carey's 2010 Oscars dress, designed by Valentino, unfortunately ended up being known for its bewildering mishmash of elements. The asymmetrical cut, paired with excessive ruching and a perplexing combination of silver and pearl accessories, certainly didn't make sense. Despite Carey's typically glamorous style, this outfit failed to deliver what was expected. On a night meant to celebrate elegance and sophistication, the musician's look became a rare fashion misstep for the iconic diva.

Whoopi Goldberg's outfit at the 1993 Academy Awards was a daring fashion experiment that unfortunately ended up on plenty of "worst-dressed" lists. The combination of fabric choices, clashing colors, and an unconventional dress-jumpsuit hybrid left everyone confused. The actor admitted that the controversy the dress caused didn't go unnoticed by her. "It hurt my feelings, I'm not going to lie," Goldberg recalled (via Page Six). "It kept me from dressing up for a very long time. You have to remember, in those days, they would say things, and you'd think, 'Do I really look that ridiculous?'" Unfortunately, Goldberg's attempt at pushing fashion boundaries fell short, serving as a reminder that not all risks pay off on the red carpet. 

Faith Hill's arrival at the 2002 Academy Awards turned heads — but for all the wrong reasons. While the texture of her dress was already eye-catching enough, the mishmash of pastel colors arranged like a rainbow turned this look into a major flop. Designed by Versace, the gown seemed to suffer from an excess of creativity, resulting in an overwhelming visual spectacle — and not in a good way: The dress failed to highlight Hill's beauty. Instead, it overshadowed her presence with its confusing design choices. And if there's one thing red-carpet fashion shouldn't do, it's overshadow the one wearing it.

Sarah Jessica Parker is known for her iconic role as the fashion-forward Carrie Bradshaw, but in real life, the actor is no stranger to fashion mistakes. The star took a risky turn on the red carpet at the 2010 Academy Awards with her pastel yellow dress by Chanel. While its silhouette showcases avant-garde and fun design elements in the front, the back of the gown tells a different story. Sadly, the odd tailoring and unnecessary detail at the bottom detracted from the overall elegance of Parker's ensemble. Despite her reputation as a style icon, even the best can stumble on occasion, and for her, it was definitely the 2010 Oscars.

When it comes to Kate Hudson's look at the 2001 Academy Awards, you either love it or hate it — and as you can guess, we're not too fond of the Stella McCartney piece. The intricate top portion of her gown, coupled with the unfortunate visibility of her lining under the train, resulted in a look that was too busy and disjointed. Luckily, Hudson wasn't too annoyed by the negative feedback. "I woke up the next morning," she revealed (via Glamour). " ... I turned on the television to find out I was on every Worst Dressed list possible. So I called Stella, and we just laughed our arses off, and she said to me, 'Look, babe, it was the hair, wasn't it?'"

Maya Rudolph's daring fashion choice at the 2018 Academy Awards caught some attention for quite a few reasons. While we appreciate an edgy silhouette, the floor-length Valentino gown overwhelmed Rudolph's frame, leaving her looking somewhat lost in the fabric. With its bold shape and intricate design, the dress could have been a showstopper with a shorter hem, perhaps knee-length or midi. Unfortunately, the decision to go full-length proved to be a misstep, overshadowing Rudolph's natural elegance and leaving us wishing for a more proportionate ensemble.

When it comes to bold and extravagant fashion, few can rival Cher's fearless style. However, her attire at the 1986 Academy Awards missed the mark for the prestigious event. While the ensemble undoubtedly showcased Cher's signature flair, its costume-wear vibe didn't quite align with the formality of the Oscars red carpet. However, there's a reason the star opted for the look. "I had the idea mostly because the Academy didn't really like me," Cher revealed about her fashion choice to Us Weekly. "They hated the way I dressed, and I had young boyfriends, so they thought I wasn't serious." Still, designed by Bob Mackie, the outfit would have been a standout hit at a more relaxed award show or during one of Cher's electrifying performances.

When it comes to Oscars fashion history, Gwyneth Paltrow's ensemble at the 2002 Academy Awards stands out for all the wrong reasons. Designed by Alexander McQueen, the outfit seemed to combine elements that clashed rather than complemented each other. The see-through illusion of the top, with the ruched middle section and the shiny black skirt, created an odd look that left us wanting more. However, Paltrow is still fond of the look. "Everybody really hated this [dress] ... but I think it's kind of dope. I'm into it," she told Vogue. "I had like a weird hangover about it for a while because people were really critical ... But I like it."

In the world of Hollywood glamour, even the biggest names sometimes stumble on the red carpet. Charlize Theron's appearance at the 2010 Academy Awards, in a creation by John Galliano for Christian Dior, left many of us divided. While the concept behind the ensemble held promise, the execution fell a bit short of expectations. The fabric seemed ill-suited to the design, resulting in an unfortunate wrinkled appearance at the hem. Additionally, the tailoring left much to be desired, with the garment appearing loose around Theron's midsection.

Uma Thurman's fashion choice at the 2004 Academy Awards was a creation by Christian Lacroix: A blue scarf belt, a patterned vest, and lace embellishments. But the resulting look was an unsatisfying mishmash of too many elements. Thurman admitted (via Time) that the choice was intentional. "We've gotten so savvy with stylists that's a kind of warfare of defensive dressing out there," she explained. "Everyone looked the same. Everyone had it down to such a perfect T. You get bored. That's when you have to say, 'I will be worst-dressed.'"

At the 2019 Academy Awards, Rachel Weisz took to the red carpet in a Givenchy Couture daring red ensemble. While the look is, in theory, edgy and fashion-forward, there's something about the mismatched textures and boxy proportions that just isn't right. While the monochromatic hue offered a bold statement, the silhouette was way too overwhelming for the star. Had the top been less boxy or the bottom less voluminous, this outfit would have easily been a show-stopper.

Zoë Saldana ventured into ombré territory at the 2010 Academy Awards, and it didn't go well. Rocking a creation by Givenchy Couture, Saldana's look attempted to mix different trends with bad success. The sparkly gold top, the curious waist detailing, the fluffy ombré bottom — all of it was too much. Separately, these elements could have worked, but together, they resulted in a fashion fiasco.

In a brave departure from the conventional, Demi Moore dared to craft her own ensemble for the 1989 Academy Awards. Yup — you read that right. The star put the look together herself, and today, she serves as a reminder as to why fashion should be left to the professionals. From the over-the-top shoulders to the unconventional style combo of biker shorts and a half-skirt, this look was simply all over the place.

St. Vincent's appearance at the 2018 Academy Awards was definitely memorable. The avant-garde musician's decision to incorporate not one but three statement pieces — a dramatic shoulder poof, an oversized bow belt, and a funky headpiece — proved to be a symphony of fashion faux pas. While each element individually possessed plenty of potential, together, the Saint Laurent by Anthony Vaccarello piece clashed, especially with the already unique-looking little black dress.

In a sea of traditional Hollywood glamour, Lizzy Gardiner dared to defy convention at the 1995 Academy Awards with her dress crafted entirely from American Express cards. While repurposing everyday materials into high fashion was undeniably innovative, the Oscars just wasn't the place to showcase this piece. When asked about it, Gardiner revealed to a red-carpet reporter, "I'm broke, and I didn't have anything to wear" (via CNN). "So I went through my list of past good ideas."

Nicole Kidman's look at the 1996 Academy Awards evoked more nightgown vibes than Oscars red carpet glamour. The Prada gown was in a stunning lavender color, which perfectly accentuated the star's hair, but the cut of it gave us a major bedtime aesthetic. Despite accessorizing with shoes and jewelry, the overall look lacked the sophistication expected at such a high-profile event.