Rare Times Kimberly Guilfoyle Has Been Spotted Wearing Glasses

Kimberly Guilfoyle has undergone a complete style transformation since her days as an attorney married to Democratic California Gov. Gavin Newsom, but it wasn't exactly a good one. Gone are the days when she used to grace parties, galas, and red carpets wearing sleek LBDs and chic young-lawyer-on-the-go ensembles with zero hair extensions in sight. Nowadays, Guilfoyle's signature look consists of tight-fitting dresses, high heels, bold and often cakey makeup, and long, voluminous hair, often making fashion and glam mistakes she should have ditched long ago. Just like her plastic surgery, which was on full display in her rare unfiltered photos, Donald Trump Jr.'s former fiancée's style seems to have gone from bad to worse, churning out many inappropriate outfits and makeup fails. However, regardless of how her style has changed over the years, there's one accessory that Guilfoyle will always have in her bag: eyeglasses. 

Even though she doesn't often wear glasses in public, Guilfoyle once revealed that her vision has needed correcting since she was a child (which might explain why her makeup and outfits look like she's never seen herself clearly in the mirror before leaving the house). "Now you know that I've worn glasses since Kindergarten! #KeepingitReal," Guilfoyle wrote on Instagram in 2016 alongside a photo of her with a pair of specs, looking very different from her usual self. 

Her spectacled look got plenty of praise in the comments, with one person advising her to "keep the glasses" because they looked "sexy as hell" on her. But Guilfoyle apparently wasn't keen on adding them to her everyday wear as she's been photographed rocking the accessory just a handful of times since becoming a prominent member of Donald Trump's circle. Here are the rare moments Kimberly Guilfoyle has been spotted wearing glasses.

It's unclear how bad Kimberly Guilfoyle's eyesight is, but she seemingly wears her glasses in public only when she has to deliver a lengthy speech and needs to read notes. This was the case when she served as a speaker at a 2019 event. In a video shared on Facebook, Guilfoyle did not wear her spectacles when she came on stage after being introduced. Instead, she donned them right before she began giving her speech and looking at her notes, suggesting she may require them only for reading.

Following her breakup with Donald Trump Jr., Donald Trump nominated Kimberly Guilfoyle to be U.S. ambassador to Greece. Guilfoyle might have wanted to look extra smart and professional to make up for her lack of diplomatic credentials, as she brought her glasses to her July 2025 Senate confirmation hearing to be ambassador. However, she might have chosen the wrong bureaucratic figure to emulate as the cat-eye glasses, pussy-bow blouse, thick eyeliner and eyeshadow, and pink lip were very much giving Roz, the glasses-wearing secretary in "Monsters, Inc."

Years before the Senate hearing, Kimberly Guilfoyle's cat-eye glasses made an appearance at the 2022 Conservative Political Action Conference in Florida. However, this had a much different vibe from her formal look during the Capitol Hill hearing. For CPAC, Guilfoyle wore large hoop earrings, high heels, a form-fitting, low-cut dress, and her specs, resulting in a sexier look. However, heavy eye makeup and glasses with thick, dark frames don't seem to be a great combination, as Guilfoyle's eyes looked like black lines behind her specs from some angles. 

Kimberly Guilfoyle's eyes also seemingly disappeared behind her glasses, overdone eyeliner, mascara, and eyeshadow at the 2022 iteration of Turning Point USA's AmericaFest in Arizona. The former Fox News host posted photos of herself at the event, showing her strutting on stage and speaking to the crowd while sporting another tight dress, large hoop earrings, and her specs. "Thank you [Charlie Kirk, Lauren Toncich, and Turning Point USA] for having me at yet another amazing AmericaFest! Let's keep saving America!" she wrote.

Though Kimberly Guilfoyle seems to have filled her Instagram with nothing but Donald Trump-related content and photos of her attending various events, she occasionally provides a glimpse into her personal life. In 2024, she shared videos of her cooking dinner for then-fiancé Donald Trump Jr. and their respective children. But aside from her admittedly bomb-looking chicken dishes, the star of the show seemed to be Guilfoyle's black-framed glasses, which made an appearance in both videos, suggesting she uses them more often when she's at home and away from the public eye. 

The cat-eye glasses might have been a newer addition to her collection, as Kimberly Guilfoyle used to wear a more flattering pair of square glasses on the rare occasions she donned specs. Her appearance at the 2020 Conservative Political Action Conference is a case point. While Guilfoyle donned her "uniform" — tight dress, thick eyeliner, and terrible hair extensions — her glasses with thin frames were more sophisticated and stylish than her cat-eye ones, elevating the look. Of course, it helped that Guilfoyle's dress also looked more appropriate and that she didn't slather her lips with concealer.

When Kimberly Guilfoyle and Donald Trump Jr. gave speeches at the University of Florida in 2019, they weren't exactly given a warm welcome. But while their $50,000 appearance was met with protests, Guilfoyle and Trump brushed off the negativity. For her part, Guilfoyle rocked her thin-framed square specs and a different but equally forgettable bodycon dress as she praised Donald Trump and made corny jokes about her romance with his son. "It's not fake news that I know Donald Trump Jr. a little bit better," she joked, per WUFT.

If we have to rank all of Kimberly Guilfoyle's glasses moments, No. 1 would have to go to her appearance at the 15th Annual GLAAD Media Awards in New York City in 2004. Then still married to Gavin Newsom and working as an assistant district attorney in San Francisco, Guilfoyle looked stunning with her rectangular glasses while presenting an award alongside model Inés Rivero. She wore the specs alongside a simple but chic little black dress and silver dangling earrings and kept her short hair sleek and her makeup soft.