Red Carpet Outfits Celebs Admit They Regret

There's one major downside to being a fashionista, and it's called outfit regret. Trends come and go, our own personal style evolves, and sometimes, we simply look back and realize we got it wrong. But the silver lining is that outfit regret happens to everyone, including celebrities. According to personal stylist Jordan, one key factor usually leads to regret somewhere down the line.

"Nine times out of 10, the reason a woman regrets her outfit choices is because she's wearing clothes that aren't truly her style," she tells Glam exclusively. "She's trying to do something, be something, or look like someone she isn't, and the end result (usually the outfit in photos) makes her feel like an imposter wearing a costume." When outfit regret happens to non-famous folks, Jordan explains that those feelings usually boil down to another reason. "Women will also regret wearing clothing that isn't a proper fit for the proportions of their body but are unable to recognize this until they see themselves in photos," she notes. "This is much less likely to happen on the red carpet because a stylist should be an expert in fitting the body and has easy access to tailoring and alterations." 

Basically, outfit regret is incredibly common. For example, Nicki Minaj didn't love what she saw when peeking back at her look for the 2022 Met Gala, the fashion event of the year. "Oh, no," she told Vogue when she saw the black, strapless gown. "I loved what the outfit was giving but I said, you guys ... these boobs are gonna be spilling out." It's never a good feeling to look back and regret, but we can take comfort in the fact that, from confident style icons like Rihanna to noughties it-girl Paris Hilton, nearly everyone has a story like this.

Rihanna made a name for herself with catchy noughties bops like "Umbrella" and 2010s hits like "Diamonds," but she's also proven to be one of the world's most-daring fashionistas, never afraid to experiment with fashion. Rihanna's stunning style transformation shows that the Bajan star was taking fashion risks right from the earliest days of her career as a teen idol, but there's one particular look she wishes she'd never worn.

"When I first started, and I was wearing like the baggy jeans, with the panties out," she told TikToker Mystery Fashionista in a December 2024 interview. "What the f— was I thinking?" Of course, the "Stay" singer was alluding to a 2005 look that saw her in baggy jeans, a pink-and-white tie-dye crop top, pink Converse shoes, and matching pink-and-white underwear poking up from beneath her jeans. "It's called growth, y'all!" Rihanna added, confirming that outfit regrets just serve to remind us of how far we've come with our fashion game.

Since there was nothing wrong with the fit or proportions here, this may have been a case where Rihanna went against her intuition to suit a trend. "Both celebrity and stylist may also be trying to push the look to fit a certain trend, message, or gain a certain level of publicity — ultimately resulting in a way of dressing that's inauthentic and contrived," Jordan explains exclusively to Glam. Notably, RiRi told the interviewer that there were other old trends she has zero regrets about, including wearing heels with sweatpants.

Tyra Banks having fashion regrets is proof that it happens to the best of us — if a supermodel who's walked for powerhouse brands like Chanel and Dior can make mistakes, it's definitely okay for you. The "America's Next Top Model" host doesn't look back fondly at the 2000 Oscars, where she turned up in a lavender ballgown by Vera Wang. To be fair, the dress was pretty and Oscar-worthy, with a strapless satin corset, drop waist, and sprawling tulle skirt. But this look failed to land for one big reason.

"I went to Vera Wang for her to dress me, and she suggested this really beautiful deep blue dress," Banks said in a 2024 interview with Harper's Bazaar. "I was like, Vera Wang, I don't want to blend in. I want to stand out! So I chose purple! Lavender! And ... I saw her face, but she was like, 'Okay, you're the supermodel.'" But looking back, Banks said the dress reminded her of "Little Bo Peep" and the purple hue rendered the 'fit "a hot mess." Fast-forward to March 2025, and Banks posted a photo of the dress to ask what her fans thought through a modern lens. "People had some OPINIONS about this dress back then," she said on Instagram. "It kinda feels like Ariana Grande would wear it in pink today."

In our exclusive chat, Jordan notes that events like the Oscars can sometimes make stars feel rushed in their decisions, so it's more likely that they'll end up with regrets. "Fittings and preliminary photos should always take place with enough time ahead of a major event, so that the celebrity can think over a decision and change her mind if something doesn't feel right," she shares. "To this effect, it's also a good idea to choose more than one option in a fitting when possible."

Love her or hate her, but Kim Kardashian is undeniably one of the leading fashionistas of the 2020s. The businesswoman and reality star doesn't just jump on the trends before anyone else — she sets them, not necessarily creating them but certainly making them viral. After all, would bike shorts and bodysuits really be a vibe this decade if it weren't for Kim? But well before she became the ultimate fashion influencer, Kardashian made a few style choices that her current self wouldn't condone. 

Back in 2006, when Kardashian was about to rise to global fame on her family's reality show, she notoriously showed up to Us Weekly's Hot Hollywood: Fresh 15 bash clad in Fendi. The look consisted of a gray knit dress worn over a white shirt with a chunky, high-waisted statement belt and knee-high leather boots. "I thought I was killing it," Kardashian told E! in 2022. "I had saved up for a Fendi belt, Fendi boots, Fendi bag." Upon reflection, Kardashian slammed this Y2K look. "I was not killing it," she said. "But I thought I was. And I probably chose to buy that than pay my rent, and I should have paid my rent." 

One of Kim Kardashian's style secrets that will change the way you get dressed is to keep it simple, so we can't imagine the Skims founder matching an oversized belt with knee-highs and knitwear today. But you never know; fashion has a way of repeating itself in the most-unexpected ways. Just look at the classic style trends staging comebacks in 2025!

Kim Kardashian isn't the only sister in Hollywood's first family to regret past fashion choices. Older sister Kourtney Kardashian has undergone a major fashion evolution, finally landing on an edgy, bold, and rock-inspired style in her 40s. So, of course, she reflects on her subtler looks over the years, like the strapless gray gown she wore to the 2009 Emmys, and shudders.

"I went to the Emmys 15 years ago, and the look was very different," she reflected in a 2024 episode of "The Kardashians." "I just wore this random gray — I don't even know the designer, I don't even know where I got it or how I even got dressed." To an objective third party, there's nothing overtly wrong with this gown — simple though it may be — but it's certainly a world away from the grungy aesthetic she prefers today. 

Whether we regret a look because it no longer aligns with our style or because it never sat right with us to begin with, Jordan recommends not holding on to those feelings. "[I would tell a person living in regret] that style is fluid and ever evolving and that what you're doing in the present moment matters far more than what you've done in the past," she tells us exclusively. So, the multitude of looks that Kardashian has worn since then that showcase her true self definitely make up for one red-carpet flop.

Eva Longoria has turned heads in her fair share of show-stopping red-carpet gowns over the years, from the deep-purple strapless number she wore to the 2008 Met Gala to the metallic Oscar de la Renta gown she rocked at the Global Gift Gala in 2024. But Longoria doesn't look back fondly on all of her dresses, especially not the gilded frock she donned to her first Cannes Film Festival in 2005.

To the untrained eye, there's nothing untoward about the sparkly, figure-hugging dress. "It looked amazing and people were like, 'Who are you wearing?'" Longoria recalled in a 2025 conversation with The Times. "I thought, 'Why are they asking me that?'" The dress might have looked fantastic, but Longoria cringes thinking about the price tag. "I went to Melrose Avenue in Los Angeles and bought a $39 dress because I was told I needed a dress," she admitted. "Even L'Oréal were like, 'Maybe next time we style you.' I really didn't understand the gravity of that red carpet."

In 2005, Eva Longoria had made her breakthrough on "Desperate Housewives," but she still wasn't a household name. Sometimes, celebrities at this stage of their careers don't have the resources to build the looks they truly desire, which leads to regrets later. As Jordan explains exclusively to Glam, this can happen whether the rising star has a stylist or dresses themselves: "Since everything a celebrity wears is borrowed and has to be approved by the label/designer, it may very well be the case that the stylist was not able to get approvals from brands that were more of a stylistic 'fit' for the client, and so they're trying to make the best of something that ultimately isn't a great match to the end goal."

Celebrities who find fame early on may be more prone to fashion regrets once they're older; how many of us regret things we wore in our teens but had the privilege of not being in the public eye at the time? Selena Gomez revealed to Hollywood Life back in 2013 that she doesn't feel great about her first few red carpets, where her go-to aesthetic included skinny jeans and sneakers. "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," she reflected (via People). "I feel like when I wore sneakers and a lot of jeans to red carpets my stylist was really mortified."

This is a case of a celebrity going against the advice of their stylist and paying for it, but Jordan notes that the opposite can be true, too. "The celebrity may not trust her own judgment, therefore deferring to the opinions of the stylist with a very different vision only to see her red carpet photos later and regret not speaking up about her apprehension," she confirms in our exclusive chat.

In Gomez's defense, she attended events like the premiere of "Pirates of the Caribbean: At World's End" in 2007, and the mid-to-late noughties did mark the rise of the skinny-jean empire. We bet she wasn't the only one rocking the denim silhouette that would dominate for the next decade! Really, the time to ditch the skinny jeans only came in 2023, and the divisive style is even set to make a comeback in 2025.

Unless you were around in the Y2K period, it's hard to comprehend just how influential Paris Hilton was. To put things in perspective, Kim Kardashian launched her career as the "closet organizer" of the hotel-chain heiress. While Paris Hilton rocked many brilliant Y2K looks in the 2000s, from baby-pink tracksuits to satin babydoll dresses to sparkling minis with matching chokers, she also had a few flops — at least in her own estimation. One standout regret was a dramatic tutu dress that she wore to the Sundance Film Festival in 2001. "It was like a black bustier with a giant pink tutu gown — it was too drastic," she told Vogue in 2020. "I wore it with moon boots because it was snowing and I couldn't wear my heels, and it was freezing so I had to wear this beanie."

Hilton revealed that she got the frock from Patricia Field, a costume designer known for her work on "Sex and the City" and "The Devil Wears Prada." With the success of the former at the time, it's understandable that the "Simple Life" star wore the outfit without asking questions. But personal stylist Jordan maintains that celebrities should never hastily accept a look. "... there should be extensive conversations around what the style is, what it isn't, and overarching details of the vision before the celebrity ever steps foot on the red carpet," she explains exclusively to Glam. "There should also be interpersonal boundaries put in place, so that the celebrity feels comfortable speaking up for herself and expressing her likes and dislikes."