Worlds Most Expensive Red Carpet Fails in History
Even the most gorgeous of our favorite celebrities sometimes have red carpet fashion fails.
The press immediately jumps all over these ill-advised outfit choices, and, to be fair, you have to wonder what these stylists were thinking.
These fashion fails are far more expensive than just wearing a pair of sweatpants to McDonald’s. The celebrities on this “Worst Dressed” list all paid thousands for their designer dresses, only to have them ripped to shreds by the media the next day.
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1. Charlize Theron
Event: 82nd Academy Awards
Year: 2010
Est. Cost: $8,000*
Charlize Theron rarely has a fashion faux-pas, so, of course, it is widely discussed when she does slip up. Many felt that the gown she wore to the 2010 Oscars was a mess, even though it was designed for her, especially by John Galliano.
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Admittedly, the floral bust accents were very oddly-placed, as they didn’t really highlight any cleavage so much as concealed it. It looked as though Theron was wearing a rose bustier, and the overall effect of the dress left much to be desired, say, fashion critics.
2. John Travolta
Event: 83rd Academy Awards
Year: 2010
Est. Cost: $1,000*
We have a lot of women on this list, primarily because they have more fashion choices (and, therefore, more options to wear something embarrassing). Men usually just wear a dark tuxedo and call it a day.
But, that was not the case for veteran actor John Travolta, who wore this ensemble to the 2010 Oscars. While blue jeans and a blazer would be considered dressed to the nines at Cracker Barrel, it fell flat at the Oscars. “Jeans” and “Red Carpet” should never appear in the same sentence.
3. Jada Pinkett Smith
Event: 94th Academy Awards
Year: 2022
Est. Cost: $15,000*
Jada Pinkett Smith had quite an eventful Oscars in 2022, to say the least. Not only did her husband smack someone across the face in her honor (causing a headline-making controversy), but Pinkett Smith also was one of the night’s worst-dressed.
Chris Rock should’ve made his joke about Pinkett Smith’s overpowering emerald dress (designed by Glenn Martens for Gaultier), which Evie Magazine named one of the Oscars’ “ugliest dresses” of the night.
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4. Celine Dion
Event: 71st Academy Awards
Year: 1999
Est. Cost: $5,000*
Nineties critics swarmed Celine Dion for her infamous white tuxedo, which she wore to the Oscars in 1999. Made by Dior, this ensemble was considered a gigantic fashion disaster by many. Dion topped her Dior pantsuit with Ray-Ban sunglasses (studded with diamonds, of course) and a fedora cocked just so.
The outfit was daring as-is, but Dion wore the blazer backward, which made the pantsuit even more of a trainwreck. Still, the singer does seem to have nine lives when it comes to her fashion choices, so this wasn’t held against her for very long.
5. Jennifer Love Hewitt
Event: MTV Video Music Awards
Year: 1998
Est. Cost: $500*
There have been a lot of badly-dressed celebrities over the years, and we might’ve forgotten about this particular look, except Jennifer Love Hewitt reposted it in 2018. The picture of her and Carson Daly brought back memories of this red carpet failure, which mixed goth and glam in an underwhelming way.
The actress wore a black, beaded minidress with a sheer overlay. Of course, we can’t forget to mention the glittery skin, courtesy of the ‘90s need to glitterfy everything. While some people thought this look was chic, others thought it was cringe.
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6. Björk
Event: 73rd Academy Awards
Year: 2001
Est. Cost: $1,000*
Bjork is known for her unique music and style, and her “Swan Dress,” which she wore to the 2001 Oscars, has been infamous since she stepped onto the red carpet that day. Bjork’s dress, which was shaped like a swan, literally, was a “tribute” to Esther Williams and Busby Berkeley.
Made by Marjan Pejoski, fashion critics have been unable to let the Swan Dress go. Bjork has said that she is “bewildered” by the critique of her get-up that year, saying she was “amazed [by] how many people thought [she] was serious.”
7. Rihanna
Event: Grammy Awards
Year: 2015
Est. Cost: $12,000*
Fans of Rihanna were split on whether they loved this dress or hated it. It was certainly voluminous, and we’re wondering how the business mogul and singer even made it to her seat that year.
The poofy raspberry gown was a fast departure from Rihanna’s other looks, which have included sheer, body-hugging numbers. The Giambattista Valli tulle gown made Rihanna look cartoonish, as though she stepped straight out of a Pixar animated movie.
8. Florence Pugh
Event: 95th Academy Awards
Year: 2023
Est. Cost: $10,000*
Entertainment Tonight described Florence Pugh’s gown, which she wore to the 2023 Oscars, as an “unlikely choice,” while People called it a “fashion risk.” Trust us, some publications weren’t so kind, as this look was an obvious fashion miss.
The poofy raspberry gown was a fast departure from Rihanna’s other looks, which have included sheer, body-hugging numbers. The Giambattista Valli tulle gown made Rihanna look cartoonish, as though she stepped straight out of a Pixar animated movie.
This Valentino look featured short black shorts underneath a voluminous gown top. The one good thing about this look was that it came with pockets, something women’s evening wear is sorely lacking.
9. Halle Berry
Event: Vanity Fair Oscars Party
Year: 2023
Est. Cost: $5,500*
Halle Berry rarely has fashion misses, as she almost always looks stunning on the red carpet. But, her Oscar de la Renta dress caused rounds of shock, awe, and absolute belief when she donned the conical mini-dress to the 2023 Vanity Fair Oscars Party.
Alas, Daily Mail was quick to name Halle Berry the leader of its “Worst Dressed” list, sharply comparing her all-black outfit to the far more stylish all-white one she wore to the Oscars. This outfit change should’ve been ditched, as searching “Halle Berry Worst Dressed” on Google brings up Berry’s look instantly.
10. Kristen Wiig
Event: 92nd Academy Awards
Year: 2020
Est. Cost: $10,000-$20,000*
Kristen Wiig is a bold actress, and we’d expect nothing less from her than a bold outfit. That said, this red and black getup might have missed the mark, even though it was designed by none other than Valentino.
Hence the famous red color, as Valentino is known for its pricey dresses, as well as its unique shade of red. The color wasn’t the issue, we’re just wondering why the dress is shaped like, as Yahoo! put it, a “hot piece of lasagna.”
11. Faith Hill
Event: 74th Academy Awards
Year: 2002
Est. Cost: $5,000-$10,000*
Don’t get us wrong, we love Faith Hill. “There You’ll Be,” “This Kiss,” “The Way You Love Me,” and many more are all bangers. But, this list is equal-opportunity, no matter how talented the wearer of these red carpet fail dresses are.
In 2002, a time when YouTube wasn’t around yet and Peaches Records & Tapes was on its last store, Faith Hill attended the 74th Academy Awards in a rainbow Versace dress. While this dress was so Y2K, it was divisive, with some calling it a “prom dress gone wrong.”
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12. Uma Thurman
Event: 76th Academy Awards
Year: 2004
Est. Cost: $9,000*
Kill Bill actress Uma Thurman arrived at L.A.’s Kodak Theater in L.A. for the 76th Oscars wearing a white-and-blue dress that got her a spot on all the “Worst Dressed” lists. Page Six was a shade nicer, describing the gown as one of the “most controversial Oscars” looks of all time.
Designed by Christian LaCroix (no, not the same LaCroix you can buy at Target for $2), the gown was meant to be different. Thurman told THR that everyone “had it down” to a science when it came to their red carpet wardrobe, and she wanted to stand out from the boring crowd.
13. Lizzy Gardiner
Event: 67th Academy Awards
Year: 1995
Est. Cost: $12,650* (After-Show Auction Price)
Costume designer Lizzy Gardiner has been in Hollywood since the early ‘90s, and she is known for her work in movies like The Railway Man, Queen of the Desert, and Hacksaw Ridge. Gardiner was never one to shy away from a bold fashion choice, and the dress she wore to the 1995 Oscars was one of her most outlandish.
American Express Gold card dress of Lizzy Gardiner
Designed by Christian LaCroix (no, not the same LaCroix you can buy at Target for $2), the gown was meant to be different. Thurman told THR that everyone “had it down” to a science when it came to their red carpet wardrobe, and she wanted to stand out from the boring crowd.
Her gown was made from over 254 American Express Gold cards. All of the golden-hued cards were authentic yet expired, and Gardiner made for quite a sight when she went onstage to accept an Oscar for her costume work.
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14. Lady Gaga
Event: 87th Academy Award
Year: 2015
Est. Cost: $8,000*
We love the way Lady Gaga’s style has evolved over the years, and she has never failed to amaze us, good or bad, with what she chooses to wear on the red carpet. Mother Monster donned a trio of Azzedine Alaia pieces to the 87th annual Oscars.
One of the pieces was a bit of a miss, due to one shocking accessory. Gaga’s Alaia dress was big, sparkling, and show-stopping, but she chose to wear a pair of gloves with it that looked like kitchen gloves you’d buy at Dollar Tree.
15. Mindy Kaling
Event: 95th Academy Awards
Year: 2023
Est. Cost: $5,000*
When celebrities take fashion risks, their choices can be polarizing. Such was the case with Mindy Kaling’s 95th Academy Awards look, which showed off her newly-toned figure (that she achieved, according to an interview, through simple portion control).
Kaling wore a cutout Vera Wang white gown, which some thought was dreadful and others thought was daring and inspiring. What do you think? Frankly, we love the NBC star no matter what she wears, fashion faux pas, or brilliant style.
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16. Kim Basinger
Event: 62nd Academy Awards
Year: 1990
Est. Cost: $1,000-$5,000*
To be fair, the ‘90s were not a fashion era that many of us want to remember, and we could have dedicated an entire list to red carpet fails from that decade. That said, Kim Basinger is one that stands out, thanks to her over-the-top look, which she wore to the 62nd Academy Awards.
Basinger, who went to the Oscars with her brother, designed her own outfit that year. Though she was inspired by Grace Kelly, this is giving us Disney’s Cinderella vibes, and not in a good way.
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17. Geena Davis
Event: 64th Academy Awards
Year: 1992
Est. Cost: $1,000-$5,000*
Geena Davis won “Best Actress” at the 1992 Oscars, and we love that for her, but we wish her outfit choice that year was better. Davis not only made the winners’ list, she also made the “Worst Dressed” roster, thanks to this half-up, half-down, satin-and-black-tights nightmare.
According to TIME Magazine, the MGM star’s Moulin-Rouge-inspired outfit makes her look as though she sees the Academy Awards as a “hilarious costume party.” To be fair, Davis does seem completely unbothered by the fact that this outfit will live on in infamy.
18. Machine Gun Kelly
Event: American Music Awards
Year: 2022
Est. Cost: $11,000*
Why is Machine Gun Kelly like this? That’s a question that has popped into our heads many times as we’ve seen the wild headlines involving the rapper-turned-rockstar. As the years have gone on and his music career has evolved, MGK has become known for being a flamboyant dresser.
To say the least. At the 2022 American Music Awards, the “My Bloody Valentine” singer donned a Dolce & Gabbana suit that was not only bright purple but also covered in silver spikes. This wool-neoprene suit was a verifiable hazard, as those spikes were all real and made from pure gunmetal.
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19. Sally Kirkland
Event: 74th Academy Awards
Year: 2002
Est. Cost: $500-$1,000*
Sally Kirkland was the “it” girl during her sixty-year career, starring in movies like Anna, In The Heat of the Night, High Stakes, Cuck, The Haunted, and more. She has been to a lot of awards ceremonies, including the 74th Academy Awards.
Kirkland wore a very ill-advised, high-low golden dress, and, though she looked like she was having fun, the bloggers were writing some not-too-nice things about her wardrobe choice. The gown looked like a mix of the French Renaissance combined with something you’d find at Spirit Halloween.
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20. Hailee Steinfeld
Event: Toronto International Film Festival
Year: 2016
Est. Cost: $5,000-$10,000*
Singer Hailee Steinfeld strutted her stuff wearing Balmain at the 2016 Toronto Film Festival, and, though the designer’s name holds a lot of weight in fashion, this optical illusion dress looks like something we’d find on a NASCAR track.
The red, orange, pink, and black dress was colorful and embellished, but even those features couldn’t save it. Compared to the other, better-dressed celebrities at TIFF that year, Steinfeld’s look totally fell short.