Even style superstars have beauty and sartorial moments they’d rather erase from fashion history.
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Jamie McCarthy/Getty; Mark Cuthbert/UK Press via Getty; Frederick M. Brown/Getty
Celebrities have tons of opportunities to make a statement on the red carpet, and sometimes they make a jaw-dropping impact, but not every outfit is a success. Whether they were just starting out in their careers and didn’t have access to the professional styling teams they’d later work with, or they took risks that didn’t work out, some of the most stylish celebrities on the planet, like Gwyneth Paltrow, Rihanna, and Emma Watson, have at least one look they’d like to erase from fashion history.
Let’s take a look at the beauty fails, funny styling mistakes, and overall head-to-toe outfits that stars regret.
Rihanna
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Jamie McCarthy/Getty
Rihanna
Even Rihanna seems to regret her outfit choices from time to time: In the April 2024 issue of Vogue, she revealed that while she initially loved the oversized brown suit she wore to the 69th Parsons Benefit Concert in New York City in 2017, she quickly wished she’d worn something different.
“It was this brown suit that we all loved, but the day I put it on I was like, ‘Uhh, this looks like something you’d give to a UPS driver.’ It’s not cute at all. Not suitable for the red carpet,” she said.
Emma Roberts
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Steve Granitz/WireImage
Emma Roberts
Emma Roberts started acting at a young age, but she says she regrets some of her early red carpet looks. The starlet hit the red carpet for the 2001 film “Blow” in camo pants, a black tank top, and a handbag made from a tire.
“For the premiere of my first movie, I styled myself,” she told People magazine in 2024. “My mom let me pick out my outfit. I had camo capri flared pants and leopard-print fur clogs. I thought I was the coolest 10-year-old in the world.”
Emma Watson
Emma Watson attended the first film premiere of Harry Potter and the Philosopher’s Stone in a long gray dress and cute black boa in 2001. 16 years later, the actress commented on the outfit choice on The Ellen DeGeneres Show in 2017.
“This was my first movie premiere and my mom and I spent weeks planning it. It may not seem like it, but a lot of thought went into this. And by the way, I thought I looked amazing. Thank God,” she said.
Kaley Cuoco
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Though Kaley “loved” the clip-in bangs she wore to the 2013 Screen Actors Guild Awards at home, she had second thoughts by the time she got to the red carpet, and when she saw the photos, she labeled her fringe “the worst decision I’ve ever made. It just didn’t work. It looked so unnatural.”
Eva Longoria
Eva Longoria attended the Tomb Raider premiere in 2001 in a brown leather ensemble, and told Health magazine in 2017 that it was her worst red carpet look. “I looked great in Tomb Raider, but it felt like I was going to a theme party,” she said.
“It’s like a time capsule, and it’s 10 years of me showing my belly. I’m like, ‘OK, Eva, can you stop wearing crop tops? Do I have to wear a crop top every time I go on the red carpet?'” she joked.
Robert Pattinson
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If I could wave a magic wand and make one red carpet look disappear, Robert Pattinson would definitely choose this one.
“I had leather pants, cowboy boots and a velvet jacket. I literally looked like a kid in a dress-up box,” Pattinson told GQ about his outfit choice for the 2005 premiere of Harry Potter and the Goblet of Fire.
Selena Gomez
During her Disney days, Selena Gomez often wore casual attire on the red carpet, but in 2013 she told Hollywood Life that she would never wear that style again.
“I remember the first time I went on the red carpet in skinny jeans and sneakers, and it was amazing, but I never want to look like that again. I remember wearing a lot of sneakers and jeans on the red carpet and my stylist was super embarrassed,” she told the website. “I’m never doing it again!”
Jonas Brothers
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Nick Jonas had to go through an awkward style phase before evolving into the fashion star he is today.
“I think we all had that Ed Hardy moment, the time when we had the hat and the T-shirt and the shoes and, if we were lucky, the jeans,” he told Racked. “It was the Dark Ages, from head to toe.”
Victoria and David Beckham
Victoria and David Beckham’s matching all-leather outfits are widely considered one of their most iconic look looks, but they have both publicly admitted to regretting it.
“It bothers me, it bothers me, but I love it,” Victoria said on Watch What Happens Live with Andy Cohen in 2022. “We were wearing Gucci, but the dinner was Versace. That in itself is inappropriate.”
David also spoke about his outfit choice: “It’s one of those things where I look back on it now and go, ‘What were we thinking?’ I laugh at the time,” the former footballer told H&M Life.
Diane Kruger
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Diane Kruger is known for taking risks on the red carpet and, for the most part, is immune to fashion criticism, she told Stylist in 2011 (via Huffington Post), but there’s one dress she admits may not have been the right vibe for the moment.
“The first Golden Globes dress I wore was by Marchesa (in 2005),” she said. “They had just started working with me and were really close friends of mine. I loved the dress they made, but it was completely inappropriate for the occasion. My belly button was showing and everyone else was wearing long, flowing gowns.”
Thomas Ian Nicholas
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Who doesn’t look back on their ’90s-inspired style with a hint of embarrassment? The American Pie star celebrated the film’s 25th anniversary by reflecting on it. “25 years ago, American Pie came out in theaters, and for some reason, I decided to wear this shirt to the premiere…”
Ashley Tisdale
Ashley Tisdale quickly learned not to use Disney costumers as her personal stylists: “They just style me the way I’m dressed on the TV show, so whenever I go out I end up looking like my character (Maddie Fitzpatrick),” she told People magazine.
At the 2004 premiere of The Incredibles, the Suite Life star wore a pink camo skirt, pink buttoned jacket, pink boots and a pink sequence bag.
“I didn’t even know what this pink furry thing was, but I was like, ‘Oh, put this on!’ And instead of just wearing it normally, I was like, ‘I’m going to stick one arm out and put this on my body.’ It was so weird,” she said. “At that point, I could only laugh at myself!”
Amanda Seyfried
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Laurence Lussier/FilmMagic
Amanda Seyfried
Amanda Seyfried now has a superstar stylist, but when she was promoting her early role in the 2004 film Mean Girls, she didn’t have a stylist, publicist, or makeup artist to help plan her look.
During an appearance on Jimmy Kimmel Live in 2022, the actress referenced one of her earliest red carpet outfits, a sheer black-and-white polka-dot turtleneck dress. “I didn’t know any of the rules, so I wore a white bra and black underwear, no slip, and I paid $600 for that dress,” she said.
Kyra Sedgwick and Kevin Bacon
Kyra Sedgwick and Kevin Bacon tried out some trends at the 1997 Golden Globe Awards, but Sedgwick jokes that they’ve since regretted it.
“I had a turquoise suit and he had a crushed velvet suit. We just got it all wrong,” the actress told People magazine in 2021. “I know I was on the worst-dressed[list]that night. I think so, and I think Kevin thought so too.”
Gwyneth Paltrow
Gwyneth admitted in a Goop newsletter that she regrets wearing an Alexander McQueen dress to the 2002 Oscars. “There were a few issues with it. I still love the dress, but I should have worn a bra, had simple beach hair, and gone easy on the makeup,” she wrote. “That would have given me the slightly punk look I wanted at the Oscars.”
Miley Cyrus
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Frank Trapper/Corbis/Getty
Miley Cyrus has been a superstar since she was a little girl, but even A-list stars can be awkward with their clothes as teenagers.
“When I was around 16 to 18, I used to dress a little questionable. I went to the Justin Bieber premiere of ‘Never Say Never’ in a hippie outfit, and who told me it was a premiere, not Woodstock?” she told Marie Claire.
Kate Hudson
Kate Hudson told People magazine in 2024 that she has no regrets about any of the clothes she’s worn on the red carpet. “I love fashion and everything I’ve ever worn has come from a creative place for me,” she said, explaining, “I know that there are some things that other people might not like, but for me, I’ve always worn and will continue to wear what makes me feel good and what I want to express myself.”
One outfit that drew public criticism was the dress designed by Stella McCartney to the 2001 Oscars, but Hudson admitted in 2011 while presenting McCartney with an award that the dress was too flashy.
“The next morning I woke up, turned on the TV and saw I was on every worst-dressed list, so I called Stella and we had a good laugh, and she said, ‘Hey, it was because of your hair, wasn’t it?'” she recalled. (She added that she’d like to wear the outfit again, but with a different hairstyle.)
Eva Mendes
The dress Eva Mendes wore to the 2007 Ghost Rider premiere was beautiful, but she says it was ruined by the styling.
“I had a dress on, but I had to get my hair and makeup done in the back of an SUV,” she explained to NBC. “It was a beautiful dress, but the outfit I wore was the wrong Princess Jasmine look. It was a strapless purple dress, a necklace, and my hair was in a high braid. It wasn’t a good look.”
Olivia Holt
Olivia Holt once attended an event in 2011 around the time of “Kickin’ It” in a white lace dress paired with black leggings and knee-high lace-up boots. She later described the outfit as “pretty scary.”
“I feel really sad that I did this to myself,” she told People magazine.
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