When it comes to getting dressed, celebrities typically experience a different approach than the rest of us. They're sent designer samples, have the latest pieces before they even hit the racks, and often have a stylist to assist with putting the whole look together (and this is without mentioning their often insane, lust-worthy wardrobes). But while celebrities usually have an upper hand, sartorially speaking, they are not immune to the occasional fashion regret.
Although celebrities like Kendall Jenner, Chrissy Teigen, and OG street style star Sarah Jessica Parker have all cemented themselves as essentially flawless fashion forces, that doesn't mean they haven't had their own share of style-related regrets. Plenty of stars have spilled their biggest fashion regret anecdotes, proving we're all human and giving hope to anyone who's ever lost their fashion footing.
Keep scrolling for the fashion mishaps your favorite celebrities regret more than anything.
Even though Diane Kruger's style can be described as downright impeccable, she's not without her red carpet regret. Her very first Golden Globes was the scene of her "worst fashion risk that certainly did not pay off," she told InStyle in 2014. She describes a daring Marchesa dress she donned for the event—"they were just starting out, and I love Marchesa and I love the girls and I don't know why we talked ourselves into this dress, which was gold, and my belly was exposed." Furthermore, she reflects how she decided to finish off her over-the-top look with retro hair: "It was not a good look, and I think that will be remembered."
There's no question Kendall Jenner currently has the street style game on lock. In her younger days, though, the story was a bit different. Like any teenager, Jenner followed along with some of yesteryear's biggest trends—namely owning an impressive collection of colored jeans. "At one point, it was really cool to have colored jeans—red, green, blue, pink," Jenner reflected in an interview with British Vogue. "I had a collection of them and would wear them every day," she admitted. "I had to wear a collared shirt to school, so I would wear bright jeans and an odd collar. It was weird!"
Alexa Chung is famous for her original style—breaking rules and setting trends. But it turns out that back in 2010, she may have been overly ambitious about just what she could get away with. When she spoke with Leandra Medine of Man Repeller last year, she recalled that she took her trendsetter status too far and donned lacy cycling shorts with a bouclé jacket and Chanel wicker basket. "I started getting invited to fashion shows, and it seemed like I could do no wrong in terms of what I was wearing," she admitted. "So I got really big-headed and thought, You know what, I can start trends. This can happen. So then I started experimenting a bit more, and the cycling shorts was the moment I realized that's not what was going on at all."
Chrissy Teigen will be the first to admit when her fashion game isn't on point. After she wore a sheer black dress to the Jeffrey Fashion Cares 10th-anniversary event in 2013, Glamour magazine posed the question, "Chrissy Teigen's See-Through Dress: Do or Don't?" Teigen hilariously tweeted back at Glamour, writing, "I am Chrissy and even I say Chrissy's look was a don't. It looks like black censor bars! Note to self: try on in the light."
Sarah Jessica Parker
Even when a celebrity look eventually becomes iconic, that doesn't mean the woman who wore it is necessarily fond of the fashion moment. Sarah Jessica Parker, one of fashion's biggest risk takers, shared her surprising style regret while speaking to Andy Cohen on Bravo's Watch What Happens Live. When Parker wed husband Matthew Broderick in 1997, she wore a black wedding dress, a choice that has since become one of her most iconic looks. "Oh, I wish it was because I was badass," Parker admitted. "I just was too embarrassed to spend any time looking for a wedding dress. There was a store that I like that I knew, and I just went and got whatever they had hanging." While her relaxed approach yielded striking results, Parker wishes she had gone in a different direction, confessing, "Now, I would do it differently."
Head to the comments to share your biggest fashion regret.