These Celebrities Agree Their Outfits Belonged On The Worst-Dressed List

Many celebrities put a lot of time and effort into preparations for the red carpet, sometimes spending months on things like skin treatments, workouts, and even posing practice. Then they have to choose the right look, paying attention to every detail, from the hair down to the shoes. Every star hopes that, after all this work, they'll achieve a stunning and memorable red carpet look. Some can even change history; the plunging Versace gown that Jennifer Lopez wore to the 2000 Grammys did help prompt the creation of Google Image Search, after all.

Even with the best of intentions, though, not every red carpet look is a hit. It's often with the passage of time that we realize how cringe-worthy an outfit was, because hindsight is 20/20 and not every look ages all that well. It's not like a celeb heads out on a big night knowing that their outfit is going to be a miss, but when the worst-dressed lists come out the next day, they definitely get the memo.

Some celebs shrug off the criticism, but not all of them. Instead of hiding their shame about their past sartorial choices, some stars actually confirm that mistakes were made. Here are 10 celebrities who actually agree that their infamous outfits belonged on the worst-dressed list.

In 1999, Gwyneth Paltrow showed up to the Oscars in a stunning pink dress; it was also the same year she won Best Actress for "Shakespeare in Love." She firmly established herself as a red carpet mainstay, but not all of her looks have been that great, and she knows it. The year after her big win, she wore a sparkly, cowl-neck Calvin Klein dress that seemed more suited to a cocktail party, and her hair was styled in a fairly boring updo. It looked like she just wasn't really trying or didn't care at all, despite being at arguably the biggest awards show of the year.

In a Q&A on Goop in 2014 about fashion, Paltrow confirmed (via Fashionista), "The Calvin Klein is an okay dress but not Oscars material. I chose it because I wanted to disappear that year." Paltrow ended up selling the dress for a good cause in 2020. However, that wasn't the only disastrous dress she's worn to the Academy Awards.

In 2002, Gwyneth Paltrow had another swing and a miss at the Academy Awards, this time with a black Alexander McQueen gown. The voluminous skirt was dramatic and interesting, but the sheer top revealed more than most celebrities might want to, and it didn't win her many fans. Former Cosmopolitan editor Marcelle d'Argy Smith wrote for BBC News at the time, "This morning Gwyneth Paltrow is probably sobbing with embarrassment. She wore a long black dress with a ruched see-through bodice that showed flat breasts — and the entire top half of her body ruched down to her non-existent waist. ... How did she leave home like that?" Yikes.

In the same aforementioned Goop Q&A from 2014, Paltrow shared what she'd do differently with the dress. "There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup," she confirmed. "Then, it would have worked as I wanted it to — a little bit of punk at the Oscars."

Apparently, 2000 was a bad year for Oscars fashion, and "America's Next Top Model" mogul Tyra Banks is the next victim. Banks wore a lilac Vera Wang gown with a large tulle skirt. It looked more like a high school prom than the Oscars' red carpet. At the time, Entertainment Weekly gave the outfit a "D" in their coverage, summing up the look by asking, "What was she thinking?"

In an interview with Harper's Bazaar in 2024, Banks shared that she viewed the dress as her biggest fashion fail. Turns out, she had no one to blame for the look but herself. "I went to Vera Wang for her to dress me, and she suggested this really beautiful, deep blue, beautiful dress," Banks told Harper's Bazaar. "I was like, 'Vera Wang, I don't want to blend in, I want to stand out!'" So Banks chose the color, and stand out she did — in all the wrong ways. Banks' final assessment of the look now? "That 'Little Bo-Peep has lost her sheep' dress that I wore at the Academy Awards was a hot mess."

Selena Gomez's career started on "Barney & Friends" when she was just 10 years old, and over the years, Gomez has given us some unforgettable red carpet moments. However, there are some looks that she'd like to forget. In her earlier years, she would take to the red carpet in far more casual outfits than you'd see her in now, such as her first red carpet appearance, which was for the 2007 premiere of "Pirates of the Caribbean: At World's End." She wore a long tank top with skinny jeans and a short vest, completing the dated look with black Converse shoes.

Gomez was barely 15, and it was on-trend for the time, so you can almost forgive her. Still, it was far too casual, and it's not a look that Gomez likes anymore. In an interview with Hollywood Life, she said, "I remember going on my first red carpet with skinny jeans and sneakers like, awesome, this is not a look that I would do ever again ... I feel like when I wore sneakers and a lot of jeans to red carpets my stylist was really mortified."

Amanda Seyfried has had quite the transformation since she had her breakthrough role of Karen Smith in "Mean Girls." All you have to do is compare her red carpet look from the New York premiere of that film to just about anything she wears now to see how far she's come. She was wearing a black turtleneck dress with white polka dots for what was her first-ever red carpet, which might have been a flattering look if her white bra hadn't shown through in photos.

"I did not have a stylist," Seyfried confirmed when asked about the outfit during a 2022 appearance on "Jimmy Kimmel Live. "I didn't know any of the rules, so I was wearing a white bra and black underwear and no slip." She's learned a lot since then, and it goes to show just how easily it can be to slip up with a red carpet look without a stylist's help.

Rihanna is a fashion star with red carpet outfits that have left us speechless, and she regularly shuts down the Met Gala. Nonetheless, even she can make fashion slips. Her outfit at the 2017 Parsons School of Design benefit in New York was one of those times. She wore a suit custom-made by a graduate from the school, which is a nice nod to the event, but even Rihanna knew that it just didn't work.

"It was a brown tan suit that we all loved so much," Rihanna told Vogue UK, "but the day we put it on I was like, 'Mmm, it's giving UPS driver,' and that is not cute. Not for the red carpet anyways." While the giant suit may have worked for a Talking Heads music video, it definitely didn't work for Rihanna.

Uma Thurman's dress at the 2004 Academy Awards was widely considered one of the worst of the night. It was a fluffy white Christian Lacroix dress with a gold waistcoat and a blue sash belt, and it's gone down in history as one of the Oscars' all-time fashion flops. The Hollywood Reporter compared it to something "a townsperson from Disney's 'Beauty and the Beast' would wear," while People said that it "made her look more like the Swiss storybook character Heidi than a sexy movie star."

However, Thurman actually went into the night knowing that it was going to be a red carpet bomb. She told The Hollywood Reporter that she wanted to stand out and be different with her outfit, even if it was in a bad way. "Everyone [else there] looked the same," Thurman said (via Evoke). "Everyone had it down to such a perfect tee in their spaghetti-strapped, sequined or chiffon, body-hugging, gym-hour promoting things. You get bored. That's when you have to say, 'I will be worst-dressed.'" Mission accomplished.

Diane Kruger started her career as a model, and she's made best-dressed lists multiple times, so she surely knows what works on her. That's why it's surprising just how much her 2005 Golden Globes outfit didn't work. She'd never been to the event before, and she certainly made an impression with her outfit, though not exactly a good one. Her hair was giving old Hollywood, but the Marchesa dress was giving "Arabian Nights."

She described it in 2014 to InStyle as a fashion risk that didn't pay off: "I don't know why, but I wore a dress, a Marchesa dress, and they were just starting out, and I love Marchesa," Kruger explained. "I don't know why we talked ourselves into this dress, which was gold and my belly was exposed. But I decided to do a retro hair; I had a short bob then. It was not a good look, and I think that will be remembered." Sadly, she's right, and she's been added to lists of the worst-dressed award show looks from a variety of media outlets because of it.

Back in the early 2000s, Eva Longoria was all about showing off her abs on the red carpet, as in, "If you've got it, flaunt it." One such midriff moment came during the 2001 premiere of "Lara Croft: Tomb Raider" in Los Angeles. She wore a brown leather pantsuit with no top, and it all felt like too much cosplay; Longoria is dressed like she's in the movie and not going to see it.

It was a pre-stylist look for Longoria that she wouldn't want to repeat. "There was a 'Tomb Raider' premiere where I wore all leather," she explained to Health in 2017 when asked about her red carpet regrets (via People). "It was very appropriate for 'Tomb Raider,' but it was almost like I was going to a theme party." As for her own midriff, Longoria said, "... there is a decade of me just showing my stomach. Like, 'OK, Eva, can you stop wearing a crop top? Must you wear a crop top on every red carpet you go to?'"

Ashley Tisdale played Maddie Fitzpatrick on "The Suite Life of Zack and Cody," and she used that show's stylist to help get her ready for the red carpet at the 2004 premiere of "The Incredibles." The result was a bewildering mix of pink, camouflage, fur, and ribbons. It's like everything in the closet was thrown on her at once with no thought behind it.

Tisdale admitted to People in 2017 (via Teen Vogue), "I wore this really weird pink camo skirt and this pink furry thing, I don't even know what it was, but I said, 'Ooh, put me in it!'" Tisdale added, "And instead of wearing it like you would normally wear it, I was like, 'I am going to do it, have one of my arms out and have it going across my body. It was the weirdest thing. At that point, you just have to laugh at yourself."

Tisdale was just 19 at the time, and who hasn't worn some questionable outfits as they were growing up and figuring out their personal style? However, not many of us wear our fashion disasters on a red carpet full of photographers, and we don't have to see the evidence of our mistakes years later.