Gwyneth Paltrow's Most Inappropriate Outfits

Since Gwyneth Paltrow's breakout roles in "Emma" and "Shakespeare in Love," the actor has been a style icon with a fabulous fashion sense that many have imitated. Known for her minimalist style, Paltrow always looks effortlessly chic and was way ahead of the quiet luxury trend that's now considered outdated in 2025. "I'm always quite partial to old French brands. I think there's always something so inherently aspirational about these brands that have existed for all these years. And the quality's so beautiful," Paltrow told Harper's Bazaar in 2024. As one of the celebrities who has re-worn outfits on multiple red carpets, Paltrow knows what she likes and sticks to it. 

Despite being a trendsetter, even Paltrow has had some sartorial misses over the years and has been caught wearing some inappropriate attire. For instance, while she's made preppy dressing her signature style, she once tried to embrace boho-chic, which didn't always translate well. From see-through mishaps to awards-show gowns that just didn't work, Paltrow has proven that even fashionistas fail at style sometimes.

Gwyneth Paltrow completely embraced the see-through trend years before it went big in the early 2020s, but she went overboard at the "Shakespeare in Love" premiere in 1999. While the Giorgio Armani dress itself was gorgeous, Paltrow could have worn a bodysuit underneath, especially in front of flashing camera lights. "I guess this was the beginning of my see-through looks, which you know, they've reared their ugly head once in a while throughout my sartorial history," she told Vogue in 2021. As for whether she received backlash over her daring 'fit, Paltrow pointed out, "There was no internet at this point."

In 2002, Gwyneth Paltrow made a styling mistake when trying to nail the see-through trend at the Oscars. The "Sliding Doors" star showed up in a black mesh shirt worn without any undergarments, and she paired it with a long, black maxi skirt. Paltrow's look was quite a departure from her usual minimalistic style, and she admitted in a Goop newsletter (via Complex), "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. Then, it would have worked as I wanted it to — a little bit of punk at the Oscars." Ultimately, this landed her on our list of the worst-dressed celebs in Oscars history.

At first glance, Gwyneth Paltrow's frock at the 2012 Met Gala looked like a minidress, albeit a very short one. It was a bit low-key for the theme, which was "Schiaparelli and Prada: Impossible Conversations," and Paltrow should have worn something with a bit more flair. That wasn't the reason the 'fit was inappropriate, however, and she told Vogue, "I guess I should mention that this was the shirt, and there was a big skirt that came with it, but I was like, 'No.'" Hopefully, Paltrow didn't have any wardrobe malfunctions that night, or her face would have been the color of the red carpet.

The Met Gala is the place to show up in the wildest looks imaginable, but Gwyneth Paltrow disappointed yet again in a shapeless, sheer yellow maxi with a ruffled high collar and pleated bodice in 2019. The "Iron Man" star's look wasn't only uninspiring for a fashion event, but it also looked as though she rolled out of bed from the 1800s and took a time machine to the Metropolitan Museum of Art that year. Perhaps she was trying to lean into the "Camp: Notes of Fashion" theme, but it didn't work for us.

Fans of Gwyneth Paltrow know that she's all for the New England coastal aesthetic, and her preppy 'fits are usually chic and tailored. However, her baggy black-and-white striped sweater paired with outdated Bermuda shorts made her look like a kid who was ready to take school pictures in 2019. Worn with white sneakers with ribbon laces, Paltrow aged herself backward, but not in a good way. A crisp, white pleated skirt or tailored jeans would have looked much more fashion-forward with her sweater.

Some people would sacrifice anything for fashion, and for Gwyneth Paltrow, that meant being unable to walk properly at the 2019 Emmys. The Goop founder made waves when she walked onstage in her vintage Valentino gown to present an award and shuffled awkwardly at a slow pace. Her stylist, Elizabeth Saltzman, later explained to The Hollywood Reporter, "That's because in 1963 there were no back slits!" She added, "In order to keep the dress authentic, I didn't want to change Mr. Valentino's design." Perhaps that's why Saltzman didn't address the small hole at Paltrow's armpit. Oops.

Now, check out how Paltrow's daughter, Apple Martin, is one of the celebrity kids who's borrowed iconic vintage outfits from their famous parents.