8 Matching Red Carpet Looks That Still Make Us Cringe

There's a saying in life: "Just because you can, doesn't mean you should." While there are many situations where this may come into play, where it really picks up momentum is when celebrity couples hit up the red carpet, or other events, in matching outfits. Yes, they may have had the means to bring these looks to fruition, but was it really necessary? Most of the time, the answer is a very stern "no."

But while that's the case, it hasn't stopped celebrities from wearing matching outfits and looking absolutely cringy in the process. In December 2025, Kylie Jenner and Timothée Chalamet, whose relationship is rife with red flags, became the latest couple to try to pull this off. Not only did they fail in their obnoxious orange ensembles, but it gave Meg Stalter and Paul W. Downs the opportunity to mock them with their own matching orange getups when attending the 2026 Critics Choice Awards. To no surprise, Stalter and Downs hilariously nailed the look, making them the best dressed duo of the night.

Of course, Jenner and Chalamet are not the first to try making matching outfits work. It has been an ongoing trend for a certain type of couple since the 1990s. Although it's a technique that's worked for the likes of Zendaya and Tom Holland, for example, for the most part these matching looks never work and still make us cringe to this day.

In one of the best examples of when matching outfits go terribly wrong, we have Victoria and David Beckham in head-to-toe leather in 1999. Not only is this a fashion moment that still makes most people cringe, but even Victoria isn't exactly keen on the matching ensembles. "It haunts me, it does haunt me, but I love it," Victoria told Andy Cohen on "Watch What Happens Live" in 2022 (via People). "We were wearing Gucci [and] it was a Versace dinner, which is inappropriate in itself... We really thought about it and there was a naïveté to it that was just so sweet." As much as it was a fashion faux pas in more than one way, it's still an iconic Victoria Beckham look we'll never forget.

In 2001, Britney Spears and Justin Timberlake — who were basically American royalty at the time — attended the 28th Annual American Music Awards in matching head-to-toe denim. Which, to be honest, was even absurd-looking for 2001. In October 2022, Steven Gerstein, the designer behind Timberlake's outfit, told Jezebel, via People, how the look came to be. "We were in New Orleans when Britney and Justin were like, 'We're doing matching denim,'" explained Gerstein, adding that they took the suit Timberlake wore on NSYNC's 2001 album "Celebrity" and remade it in denim. "We had some crossover contacts at Levi's, so it went from being an idea to it being made within days." Ever since, these looks have lived rent free in the heads of both fans and non-fans alike.

If you thought that denim debacle was the only time in their relationship that Britney Spears and Justin Timberlake tried to make matching outfits happen, then think again. In November 2001, the couple arrived at Spears' record release party for her album "Britney," donning coordinating shades of yellow, mustard, and brown. While certainly not as bad at the denim attempt a few months prior, this still isn't exactly a good look for them as a couple — or even separately, for that matter. Sure, the early aughts had some of the worst fashion in recent memory, but these two really could have taken a different route here.

As much as many of us would like to forget Kanye West exists for a whole boatload of reasons, we can't ignore his less egregious offenses, like this look. During Paris Fashion Week in 2022, West was spotted at various events with Julia Fox, a celebrity who really takes the classic cat eye to a new level, and the two were wearing these heinous matching outfits. To no surprise, despite the haute couture designers involved in these pieces – Fox's jacket is by Schiaparelli and West was in Balenciaga – it was "Ye" himself who styled he and Fox... and it shows.

If you're a celebrity who goes out of their way to dress in something to garner attention and that attention isn't enough, your best bet is to try again; and, of course, make sure to up the ante the next time around. That's exactly what Kanye West and Julia Fox did in January 2022, just one day after their matching denim ensembles. When the two attended the Schiaparelli Haute Couture Spring/Summer 2022 show, they went for matching leather outfits and, because Ye didn't get the commotion and ruckus he craved, he put what appears to be a cotton bag over his head. Considering the comments he'd make in the months to come, covering his face tracks.

Because Timothée Chalamet has been applauded for his fashion sense, it's hard not to wonder who thought this matching look was a good idea. Yes, it makes sense for the Los Angeles premiere of "Marty Supreme" that there would be some orange, an homage to the ping pong balls in the movie, but this choice — all of which was designed by Chrome Hearts – is tacky and ridiculous, right down to the orange Timberland boots on Chalamet. Not only are we still cringing, but when these two look back at this photo years from now (if not sooner), they're going to know exactly how Britney Spears and Justin Timberlake feel about their 2001 denim moment.

Another matching Victoria and David Beckham memory from the early 2000s? You better believe it! While the couple have often coordinated outfits — and have done so amazingly well — in the early aughts, the majority of their attempts were painful on all the senses. For the 2003 MTV Movie Awards, the couple showed up in matching white outfits. Although David went for a suit, which he accessorized with earrings and a large diamond cross necklace, Victoria decided on this embellished and bedazzled lace-up dress with a small train. It may never be as bad as the matching leather outfits, but it's also not a proud style moment for either one of them.

In December 2021, Sarah Brady and Jonah Hill officially made their red carpet debut in matching pale blue Gucci suits for Hill's film "Don't Look Up." Not only were the suits identical, but so was how they wore them, with Brady flawlessly pulling off a topless blazer moment. At the time, the matching suits and shoes were simply cheesy and eye-roll-inducing. However, when the two broke up the following year and Brady chose to publicize text messages from Hill in 2023, which revealed the bullying and control he had over her, the matching suits took on a more sinister tone. Now we're cringing over this fashion moment for other reasons, too.