Brooke Shields Outfits That Totally Missed The Mark

Brooke Shields has been in front of the camera for the majority of her life. Ever since that iconic, controversial 1980 advertisement for Calvin Klein, Shields has remained a recognizable figure in the entertainment industry. She also pretty much put bushy eyebrows on the map by not only embracing them, but looking chic while doing so.

Although Shields has always been an integral part of the fashion world in her own way, as she's gotten older, her relationship with clothes has changed. "For the first time, I am looking at clothes with a sense of my own taste," Shields told Harper's Bazaar in January 2025. "For so long, I either was just doing a modeling job for other people or I was trying to look like other people, and now I'm working with different stylists who understand different parts of who I am." As one of the celebrities who's confronting aging with confidence, Shields explained to the publication that now, at 60 years of age, she likes her body differently than when she was young and has learned to give herself and her body grace.

While Shields is someone who hits it out of the park with her outfits most of the time, some of her looks have missed the mark. Whether it's the event or the color and design of a certain dress, Shields has had her fair share of fashion moments that she may want to forget. Or, at the very least, pass the blame on to her stylists.

In February 2015, Brooke Shields attended the New York premiere of "Kingsman: The Secret Service." Although she wasn't in the film, which lessens the pressure of pulling out all the stops when choosing an outfit for such an event, because it's still a film premiere, you want to at least look like you made an attempt. However, Shields looked rather undone — especially for someone of her caliber in the fashion world. Not only was her dress rather ill-fitting, and the fabric wasn't taken into consideration regarding paparazzi camera flashes and the undergarments it would reveal, but even her shoe choice — which appeared to be flats — was perplexing because they were so boring.

As we all know, monochromatic looks make for winning outfits on lazy days, but when you're attending the Time Women of the Year Gala at the Four Seasons in Los Angeles, of all places, maybe head-to-toe pink isn't the best option. That being said, this was the outfit Brooke Shields wore in March 2023 to that particular gala, and it was far too much bubble gum pink for such an event, especially since she carried the color all the way down to her heels. There's also the matter of what's going on under the blazer: was it a two-piece ensemble or a strange take on a jumpsuit? When an outfit offers more questions than answers, you know something is off.

There's no denying that a silver sparkling jumpsuit is a lot of fun, as is the fact that Brooke Shields clearly paid homage to the 1970s with the outfit and her hair. But the issue here was in the length of the jumpsuit: it was too darn long. Considering Shields wore this to the 2019 CFDA Fashion Awards, you'd think she — or her stylist — would have paid closer attention to the details, making sure it fit Shields' frame perfectly. Instead, it looked a little sloppy, something that could have been avoided by sticking to the universally flattering clothing hack for every shape and size: tailoring.

When Brooke Shields attended the "Yellowstone" premiere at the Museum of Modern Art in November 2024, she opted for a color that really didn't do her any favors. While the design and cut of the dress fit Shields perfectly, and the boots brought the whole look together, while also giving a subtle nod to the theme of "Yellowstone," the shade of brown wasn't right for Shields. Between her hair color, which wasn't much darker than the dress, and her skin tone, the sandy hue really washed Shields out. Of course, the yellow backdrop didn't help all that well either.

While black cigarette pants and matching heels are pieces that will never go out of style and look good on everyone, Brooke Shields' shirt situation genuinely made us wonder if this fashion icon lost a bet or if someone stole her mirror. Granted, Shields wore this to Take Home A Nude to benefit the New York Academy of Art at Sotheby's in October 2016, so it's not a gala, but that still doesn't excuse the shirt. It's not just about the cut-out shoulder, but that it looked like someone blindly took scissors to her garment, then convinced her it was cool and flattering. Unfortunately, that was not the case.

While it's always fun to play with color, some colors — like we saw with her bubblegum pink look — can just be too much. In September 2024, for an appearance on "GMA," Brooke Shields arrived in a bright orange suit and proved she really has a thing for taking bright and bold colors to places they simply shouldn't go — like an interview for a morning show, for example. While we've learned that Kate Middleton can turn a pantsuit into a sleek fashion statement, she seems to be one of the few — something that Shields basically confirmed in her own way when she left the house in her orange outfit.

In 2016, for the opening of Cirque Du Soleil Paramour on Broadway, Brooke Shields decided to go a little casual, which is fine for an event like this. What's not fine was the cut of the dress and how uncomfortable Shields looked. Between the halter top and keyhole in the center of the bust, it looked like a dress that was trying to appear relaxed and cool, but was actually strangling Shields. To make matters worse, the fabric's pattern and belt-like design through the waist made Shields look far shorter than she actually is. When you're six-foot, and your dress makes you look 5'4", you know it's not the best design for your frame.

For the 32nd Annual Rita Hayworth Gala for the Alzheimer's Association in October 2015, Brooke Shields wore a fabulous art deco-inspired dress, and, in theory, it was perfect. However, it just didn't seem to work in the real world, and not even Shields could save it. While some dresses are meant to accentuate certain features, like the hips, this dress did that by accident. The curved drop waist made Shields look very wide through the hips, while the length brought a dowdiness to the entire ensemble. Although the embellishments were stunning, the design simply didn't work for Shields.

In August 2012, Brooke Shields attended the LA premiere of "The Campaign" with her husband Chris Henchy and wore a woefully unflattering dress — even by 2012 standards. Not only were the colors — especially the neutral paneling — not a good choice for Shields' skin tone, but the dress simply didn't fit her correctly. While colorblocking dresses can work, if you haven't taken colorblocking 101 to learn about how to rock the trend, then some attempts will fall flat, as evidenced here. Another interesting detail about this dress, and not in a good way, was how the ruching along the side seemed uneven, making the overall ensemble look cheap and borderline tacky.

While Brooke Shields leaned into the polka dot renaissance without looking too twee, she also looked like she was being swallowed whole by all those dots. It's not just the fact that the polka dots were huge, making the dress look gaudy, but there were so many of them. Had Shields opted for a mini dress with dots of the same size, the look would have been playful, fun, and very flattering. Instead, it was overwhelming, even for someone of her height. But Shields definitely scored points by completing the look with a bold red lip and matching clutch.