Jarring Pics Of Kimberly Guilfoyle Prove Her Makeup Should Never Be Captured Up Close

There have been countless times where Kimberly Guilfoyle's tasteless makeup was out of place. Regardless of the situation, Guilfoyle seems compelled to wear cakey makeup. To promote the release of her children's book in May 2024, the one-time "The Five" host donned a low-cut white dress while holding up the book in a snap posted to Instagram. Naturally, she made sure to apply heavy eyeshadow and mascara, and to darken her eyebrows. It was difficult to pinpoint the vibe that Guilfoyle wanted to exude, as the dress and excessive beauty products combo didn't read as motherly to promote a children's book. She also used a photo filter which helped obscure just how much makeup was used. Relying on a filter is a tactic she often employs.

It's rare to find, but unfiltered photos expose Guilfoyle's extensive cosmetic work. To celebrate Donald Trump's inauguration in January 2025, Guilfoyle made her way to Washington, D.C. along with other members of Trumpland. A candid selfie was posted to Instagram that showed how much Guilfoyle's appearance had been altered. The smokey eye look (prevalent in virtually all her photos) was evident, but so were the cosmetic procedures she appeared to have undergone, such as cheek filler and lip filler.

Months later, another semi-candid pic was uploaded to Instagram of Guilfoyle without a photo filter. That was taken at a White House party in May 2025, and Guilfoyle's face filler looked to be melting. She had her requisite makeup caked on, but while the photo captured her dissolving injections, it failed to fully portray just how much makeup had been applied. Below are examples that show how jarring Guilfoyle's makeup can look when caught up close. 

Kimberly Guilfoyle's cakey makeup was a distraction at the Republican National Convention in July 2024. She delivered an impassioned speech to the pro-Trump crowd, and made sure to speak to the back of the room — with her makeup. Those in attendance didn't need the big screen to see that the former Fox News personality went ultra-heavy on the makeup. Her eye shadow and mascara were excessive, and so were her eyebrows that had been filled in. A close-up shot showed that Guilfoyle had a generous portion of foundation, along with ample blush on her cheeks. The effect under the lights caused her face to be multi-colored.

Kimberly Guilfoyle's unfiltered face was on full display in a photo captured from Donald Trump's inauguration. The pic was uploaded to Instagram by TV personality Myrka Dellanos in January 2025. For that inauguration event, Guilfoyle sported a multi-colored floral patterned dress with a plunging neckline that gave people an eyeful of her assets. Those viewing the picture were also given a clear view of how Guilfoyle's makeup looked without being airbrushed by a filter. Not only was the foundation caked on, but so was the eye makeup, as she rocked faux lashes with oodles of mascara piled on. On top of that, the combination of lip filler with a bold choice of lipstick made her look particularly unnatural. 

In hopes of making an impression on the red carpet at the amfAR Gala at Cannes in May 2025, Kimberly Guilfoyle wore a revealing red dress. Half of the top was transparent mesh, with carefully placed stitching to keep the outfit SFW. To match the outlandish dress, the Rumble media personality went all out with her makeup. She had too much rosy blush on her cheeks — which looked to have been touched up with filler — and a liberal amount of bronzer. The matte beauty products gave her skin a waxy, unnatural hue under the bright lights. Guilfoyle topped it all off with a wild amount of eyeshadow and mascara that gave her an Ursula from "The Little Mermaid" effect.

At Day 2 of the Republican National Convention in July 2024, Kimberly Guilfoyle rocked a cobalt blue dress with a plunging neckline that showcased her figure. While those in attendance were given an eyeful of her curves, Guilfoyle also made sure her facial features stood out. Her signature smokey eye look was in overdrive, and she also appeared to pay special attention to her eyebrows, which looked to be filled in with a thick Sharpie. The combination of the cakey eyeshadow and mascara in conjunction with the eyebrows gave her a villainous aura. Guilfoyle also didn't skimp on the lip gloss to highlight her plump lips that seemed to have been touched up with filler just before the event.

Following her unceremonious break up with Donald Trump Jr., Kimberly Guilfoyle was appointed as the United States Ambassador to Greece. She was sworn in to the position in September 2025, and her official photo was shared online. Aiming for an air of professionalism, the former Fox News correspondent went relatively light on the makeup — but she still liberally applied the eye basics. Naturally, she still had on a lot of foundation and blush, but it was her pout that made a statement. Guilfoyle's overly-injected lips were smothered in a light hue of lipstick, which made them stand out by contrast compared to her smokey eyeshadow.

Congrats to our new ambassador to Greece, the cradle of western civilization and the birthplace of democracy pic.twitter.com/3LEFTjI2fM

— Clue Heywood (@ClueHeywood) November 7, 2025

Kimberly Guilfoyle was on hand offering emotional support to Donald Trump as he addressed a crowd at the Trump National Golf Club after being arraigned on federal charges. For the occasion, Guilfoyle wore an all-white skirt suit ensemble with the jacket draped over her shoulders. Wanting to be ready in case cameras caught her reaction to Trump's speech, Guilfoyle packed on the eye makeup. That day, her eyelash extensions were even more pronounced, as a close-up shot from the side showed her flashing an exaggerated smile that matched her overly-embellished lashes.