Pics That Prove Matching Red Carpet Looks Always Land You On The Worst-Dressed List

Every awards season, viewers can expect to see celebrities get dressed in their finest clothes to walk the red carpet. However, some celebs don't always get it right, and it's always painful to see. Especially when there's a couple providing not one, but two bad looks. Still, some people with more disposable income than they know what to do with are still the worst-dressed celebrities on the red carpet, even when they have the funds to avoid wearing a bad outfit.

One of the guaranteed ways to end up on a worst-dressed list is to be one of those matchy-matchy celebrity couples — the ones who refuse to leave the house until everyone knows they came to the event together. While we can appreciate the love, a matching red carpet look rarely works. And if it does, none of the ones below match that description.

Kylie Jenner and Timothee Chalamet's matching red carpet outfit for the Los Angeles premiere of "Marty Supreme" in December 2025 quickly put them on several worst-dressed lists. Many who saw the matching look online compared them to Halloween pumpkins and traffic cones, as well as declaring the 'fits overall tacky choices for a formal Hollywood event. While Chalamet broke the orange color block with a black crossbody bag, the couple were head to toe in carrot.

Before they were involved in a public fallout with their eldest son, Brooklyn Beckham, Victoria and David Beckham had a memorable fashion no-no in 1999 at the Versace Club Gala Party in London. The couple were photographed wearing matching leather outfits with questionable hair. Even in the '90s, they looked more like they were going to a motorcycle convention than a high-fashion event. Victoria told Andy Cohen on "Watch What Happens Live" that the look "haunts" her every time she sees it, though she loves it regardless. At least someone does.

During the 2016 Met Gala, Kim Kardashian and Kanye "Ye" West wore matching metallic outfits designed by Balmain. Kardashian looked as if she was channeling a disco ball with badly sculpted eyebrows and makeup that made her face look washed out. West also missed the mark, though, instead of bad, he went downright scary. His piercing, silver eye contacts made him look as if he was going trick-or-treating or acting on the set of "X-Men" rather than attending the Met Gala. 

Jonah Hill's relationship with Sarah Brady made headlines when she accused him of being emotionally abusive and shared unflattering texts between them. But before their messy breakup, we only judged their fashion choices. Their matching blue Gucci suits at the premiere of "Don't Look Up" in December 2021 screamed Jeff Daniels in "Dumb and Dumber," minus the hat and cane. Hill also insisted on showing us his bare chest under his blazer while Brady remained buttoned up.

Timothée Chalamet and Kylie Jenner's matching orange outfits were so cringe that it was quickly recreated for those who hated them to judge all over again. The culprits of the parody were "Hacks" stars Megan Stalter and Paul W. Downs. During the 2026 Critics Choice Awards, Stalter and Downs appeared on the red carpet wearing a replica of the couple's viral look, which was styled by Taylor McNeil. On the red carpet, Stalter joked that she borrowed the dress from a "really close friend." 

Don't hate us, but Britney Spears and Justin Timberlake's denim look is a fashion nightmare. Their combined determination to add as much denim as humanely possible at the American Music Awards in 2001 made the look even worse, as no one ever needs to replicate denim accessories. Still, the look remains one of the most memorable red carpet moments for both Spears and Timberlake. The "Toxic" singer shared in her 2023 memoir, "The Woman In Me," that she loves how much their fans adore and recreate the look today. 

Beyoncé and Jay-Z rarely miss when it comes to fashion. But unfortunately, even one of the richest and most fabulous couples get it wrong on the red carpet once a matching look is involved. In 2004, Bey and Jay made their first red carpet appearance together by stepping out from a yacht at the MTV Video Music Awards. Maybe it was the excitement of making their relationship official or something else, but this look seemed like they didn't coordinate until about an hour before the event.

Megan Fox and Machine Gun Kelly's relationship was quite interesting while it lasted, blood drops and all. But at the 2023 Grammy Awards, Fox and Kelly completely missed the mark. They wore matching shiny outfits that just didn't work for either of them. Kelly channeled a roll of aluminum foil in a metallic Dolce & Gabbana suit and overshadowed Fox's white Zuhair Murad gown, which was designed with a basic mermaid silhouette. 

Although Evan Peters and Halsey didn't work out after dating from 2019 to 2020, they were together long enough to make a terrible fashion choice. In October 2019, they made their red carpet debut at an "American Horror Story" event with matching outfits that paid homage to the iconic couple Sonny Bono and Cher, mustache and all. The colorful look was a complete replica of how the former duo dressed in the 1970s, and that's exactly where they should've left it.

At the 2014 VMAs, 13 years after Britney Spears and Justin Timberlake's infamous matching denim look, Riff Raff and Katy Perry recreated the look for a 2010s upgrade. Rather than completely replicating the outfits, the pair decided to make it a bedazzled mess. We truly don't know which version of denim-on-denim is worse, but since Riff Raff and Perry weren't in an actual relationship and didn't have love on their side, we're picking them.

Alicia Keys and Swizz Beatz attended the 2025 Met Gala in bright red and burgundy pin stripe suits. The effort was there, but they both got their look horribly wrong. The suits' colors didn't fit either one of them. Additionally, Keys' headdress overshadowed her face and, while the coat matched the look, its bulkiness made us wonder how many times she tripped on the steps that night. We also could've gone without Beatz's burgundy durag and sunglasses. 

Will Smith and Jada Pinkett Smith usually dominate on the red carpet. However, everyone makes mistakes, even an impeccably stylish couple like them. In 1997, the Smiths attended the Academy Awards wearing matching lime green outfits. It was one of the rare times it didn't fit their aesthetic. They appeared to not have the same shade of green on, and Will Smith barely matched with his wife.

Exes Bella Thorne and Mod Sun decided to represent the clothing brand MCM at one of their events in 2019 by wearing matching blue and white outfits and accessories. While we understand that paying homage to a designer is a sign of respect, there was nothing respectful about this look. It's a good thing the couple didn't stay together long enough to keep their cringe-worthy red carpet looks going.

When you think of 2000s nostalgia, it's difficult not to remember that, in this very same universe, Jennifer Lopez and Sean "Diddy" Combs were in a serious relationship. One of the highlights of their relationship was their matching white 2000 VMAs look that is still often discussed. However, while many pop culture lovers saw their matching look as cute at first, something tells us a fashion icon like J.Lo wouldn't be caught dead wearing a bedazzled bandana today. Diddy's gaudy cross chain is also unnecessary.

Joe Jonas and Sophie Turner, who were married for five years before divorcing in 2024, graced the 2019 Met Gala carpet soon after they wed. The former couple's Louis Vuitton looks weren't bad, but didn't quite suit them nor fit the event's "camp" theme, though Turner's smoky-eye makeup helped. The bright colors also made the "Game of Thrones" star look paler than usual.

Zayn Malik and Gigi Hadid had some ups and downs during their seven-year romance, and one of them came in 2016 when they appeared at the Met Gala for the first time as a couple. While the Met is all about costumes and thinking outside of the box, Malik's "I, Robot"-inspired look was a bit much. Hadid's choice to wear sequins instead of armor shows she probably felt the same way.

Nick Jonas and Priyanka Chopra seemed a little too eager to keep the spark alive in 2019. One year after their two wedding ceremonies in 2018, the couple proved they were still deep in wedding mode. At the Cannes Film Festival that year, they wore matching blush outfits, with Chopra posing in a blush gown and Jonas wearing a white suit and a blush bowtie. We don't hate it, but it would have been more suited for a third wedding rather than the red carpet.

When two of the most talented movie stars get together, you don't expect them to not know how to pull off a red carpet look. However, such was the case for Kirsten Dunst and Jake Gyllenhaal. The A-listers, who dated from 2002 to 2004, were often adorable to see on the red carpet. But their 2003 Met Gala debut wasn't one of them. The outfits reek of a time in the early 2000s when you thought it was okay to wear a beanie with a formal gown.

For some reason, there are celeb couples who get together and instantly start craving a matching denim look, though it never quite ends well. However, that didn't stop one of Hollywood's strangest couples, Kanye "Ye" West and Julia Fox, from trying their version of the trend. They briefly dated right after his and Kim Kardashian's divorce, and their relationship thrived on outrageous fashion choices, like this one. While we can't deny the creativity (Fox's cone-breast jacket), it still fell flat — pardon the pun.

Even a couple as adorable as Bethany C. Meyers and Nico Tortorella got it wrong on the red carpet. The couple, who married in 2018 and share two children, attended the red carpet at that year's MTV VMAs looking as if they stepped out of a Green Day music video circa 2004. While MTV is where rock n'roll thrived in the 1980s, 1990s, and even early 2000s, the look didn't do much for either of them in a new decade.