7 Times Kimberly Guilfoyle's Spicy Style Made Her Look Older Than She Is

If there's one thing you can say for sure about Kimberly Guilfoyle's style, it's that she certainly knows how to turn heads. The current U.S. ambassador to Greece is known for wearing 'fits that show off her figure, but not always in a good way. In fact, Guilfoyle has been seen in some outfits that were beyond tacky and made her look older than her 50-something years. It's clear she's trying to hold onto her youth with low-cut dresses, lots of bling, and teeny tiny crop tops, but when you're at a certain age, those styles can actually age you.

You'll rarely see Guilfoyle in casual outfits, and her over-the-top ensembles have even caused a few wardrobe malfunctions, such as her see-through dress at a 2019 NYFW show that clearly revealed she wasn't wearing a bra. Still, an embarrassing fashion moment won't deter Guilfoyle from stepping out with some gaudy attire, and several of her choices gave off the impression that she's desperately trying to hold onto her youth.

Sweater dresses are great for when you want to throw something on without giving it a second thought, but Kimberly Guilfoyle chose the wrong era to wear hers. The tight red sheath she had on in February 2026 was so outdated with the slit cuffs and keyhole neck that it looked like she found it in an '80s clothing bin. These days, a looser fit is more in style, as is a simpler dress, without all the tacky features like Guilfoyle's, which just shows how clearly out of touch she is with today's fashion.

Kimberly Guilfoyle has worn some cringe-worthy outfits, and her 2018 getup for a Hamptons Memorial Day event was right up there. From her polka dot crop top to her low-rise red capri pants, it looked like Guilfoyle was trying way too hard to fit in with a younger crowd. However, you'll never see a Millennial or Gen Z wear this type of outfit, especially after the mid-aughts. It seems the former prosecutor is a few years too late with her fashion, yet again.

Fashion Week is the time to step up your sartorial game, especially if attending a Paris haute couture show, but Kimberly Guilfoyle dropped the ball with another failed attempt in January 2026. The sheer silver dress in a gauzy material covered in haphazardly placed rhinestones didn't feel high-fashion at all, and seemed to be chosen only because it looked like something someone decades younger would wear. On the other hand, Carla Bruni looked more appropriate and runway-ready in her black lace top and dramatic cape. Guilfoyle should take lessons from the former model.

While LBDs never go out of style, wearing too much black is an outdated fashion trend that instantly ages you. In 2018, Kimberly Guilfoyle showed up at a restaurant opening in New York City wearing a black long-sleeved wrap dress and pumps without a hint of accessories. Not only did the dark color make her look older, but the knee-length silhouette cut her off at the legs and gave her a frumpy appearance. A shorter hemline and perhaps some colorful jewelry would have refreshed Guilfoyle's whole 'fit.

In one of her wildest looks yet, Kimberly Guilfoyle showed up to the 2025 amfAR Gala in a sheer, lacy red gown that left very little to the imagination. It wasn't just inappropriate for the non-profit organization dedicated to HIV and AIDS research, but it was also painfully obvious that Guilfoyle wanted all eyes on her. While posing on the red carpet, she looked like an aging pageant queen who wasn't ready to give up her crown. From the cheap-looking netting to the singular puffy sleeve and gaudy, vine-like embellishments, this out-of-touch look aged her in a big way.

Fashion shows just aren't Kimberly Guilfoyle's forte when it comes to serving looks. In 2017, she arrived at designer Zang Toi's show during New York Fashion Week in a black knit dress covered in white floral appliques. The large print, combined with the knee-length hem and cap cut sleeves, looked like something a grandmother would grab at a department store. It certainly aged Guilfoyle by at least a decade, and if this was in fact Toi's creation, he needs to rethink what looks good on women.

Along with sheer fabrics, Kimberly Guilfoyle loves a sparkly moment. However, sequins only highlight that she's reached a certain age. As fashion expert Shane Watson told the Daily Mail, "Even though they're a Christmas party classic, sequins are high up the list of things that can make the over-50s look dowdy in an 'occasion dress' way." And he's not wrong. If you look back at episodes of "The Golden Girls," you'll see a plethora of sequined dresses worn by the stars. While Guilfoyle's heavily face-tuned pic made her look years younger, her outfit choice was a dead giveaway.