Supermodel Cindy Crawford Has Had A Few Rare Fashion Flops Over The Years

The idea of the supermodel is a relatively modern creation, with many of the earliest to be called such still alive — and modeling — today. One of the biggest names of '90s fashion, American model Cindy Crawford, formally stepped away from walking the runway full-time in 2000but has by no means exited the public eye.

In addition to some scattered catwalks, campaign shoots, and stepping out with her daughter, model and actress Kaia Gerber, her philanthropic work also has her posing for cameras fairly regularly. Best remembered for her athletic figure and amazing hair, the model turned businesswoman also released lines of workout videos, a furniture line, and her longstanding cosmetic brand, Meaningful Beauty. She's hardly changed at all since she won the  Elite Look of the Year at just 17, and there's no doubt that her consistent workout regimen and focus on skincare have helped maintain her radiant and minimal makeup glow.

Her sense of style has also remained incredibly relevant and on-trend, pulling together both business casual looks, as well as a more formal glam to the red carpet. However, after more than four decades in the industry, it would be impossible for Crawford not to miss the mark at least once. While they are few and far between, here are a few of her fashion flops over the years.

Love, in a lot of ways, boils down to a certain sense of harmony. However, while her relationship with her husband, business tycoon Rande Gerber, is stronger than ever, the same can't be said about this black cutout dress she wore to the Keep Memory Alive "Power of Love" gala benefit on Valentine's Day 2026. 

The stretchy, soft material of the long-sleeved black dress creased awkwardly at the several circular holes on the side of the dress, detracting from her typically more refined and structured sense of style. While undoubtedly comfortable, the dress would have been just as chic sans the peekaboo side-view.

Crochet has been a knitting technique since the 18th century, but the 2010s Coachella music festival fashion trend certainly helped solidify it as a boho staple in the American fashion psyche. Cindy Crawford may have been trying to channel some of that free spirit at the Best Buddies' Celebration of Mothers in May 2023, but ultimately it felt like a trend hopped on a decade too late. 

The awkward X-pattern made it appear edgier than what was probably intended, and she probably could have styled the underlying slip dress with the same beaded belt, bag, and brown sandals to the same effect.

Cindy Crawford walked for several of the biggest fashion houses of the '80s, '90s, and beyond. However, just because something is designer doesn't exclusively mean that it's the best possible look. In theory, this magenta lace Versace number from the Clooney Foundation For Justice's "The Albies" event in September 2023 could have been an iconic nod back to her 1992 MTV Awards look by the same designer. However, the sporadic silver safety pins scattered across the bodice didn't have as great an impact as the original golden buckles. We can't directly blame Crawford, but we'll take it up with Donatella.

Cindy Crawford typically elevates business-wear masterfully, but the styling of this black, shoulderless blouse tucked into a high-waisted camel pencil skirt at the Women's Guild Cedars-Sinai Annual Luncheon in 2019 was not her brightest moment. The slouching at the chest was a silhouette-blocking nightmare, and sat awkwardly atop the waist-cinching bottom. Maybe if the top had been somewhat tighter, or the waist of the skirt had been somewhat lower, the pieces could have fallen in a way that was more flattering. The color palette undoubtedly had the right idea, but unfortunately, gravity could not let the look sit right.

We've all jumped on trends that don't really resonate with us, and not even multi-millionaires like Cindy Crawford can pay their way into pulling something off. In this photo of her and her husband, Rande Gerber, walking hand in hand at the Mert Alas x Marcus Piggot book launch party in 2017, Crawford debuted an unconventional burgundy jumpsuit with black zipper detailing. Although athletic wear has always looked stunning on her, this more utilitarian piece fell awkwardly and felt painfully trendy. The black leather jacket softened the blow slightly, but the model should focus on making trends — not following them.

Cindy Crawford's 2009 blue metallic Versace Met Gala look was so good, but not every Met Gala look lived up to that iconic dress. She showed up to the event in 2019 wearing custom Balmain and fell into the nude-look trap that so many others do — the shade mismatch. 

The nude panelling among the reflective mirrored pieces was several shades lighter than her skin tone, shattering the seamless illusion. Maybe she should have skipped tanning ahead of the event, but ultimately, this is such a common struggle among any woman seeking a formal dress; it brings some humanity to the supermodel.