Kimberly Guilfoyle's Most Embarrassing Makeup Moments

Kimberly Guilfoyle's beauty transformation over the years is a lot like Donald Trump's political views: the change is so drastic that it makes less sense than Donald's strange obsession with Hannibal Lecter. Guilfoyle's future-father-in-law once donated money to the campaigns of Democratic politicians — including Kamala Harris — while Guilfoyle once sported subdued makeup. But nowadays, she has a tendency to overindulge in the bronzer, mascara, and foundation.

Back when Guilfoyle was married to California Governor Gavin Newsom, she was capable of restraining herself from emptying half an eyeshadow pan to paint her eyelids. Her makeup started to become heavier after she joined "The Five" panel on Fox News. Her lips were glossier, her top and bottom lash lines were rimmed in black, and she was using a darker shade of foundation because her skin had gone from porcelain white to bronze. Of the network's beauty standards, journalist Jami Floyd once told Allure, "It was Fox that changed everything: a Victoria's Secret ethos driving what you look like on TV." But it wasn't the final stop in Guilfoyle's aesthetic evolution.

When Guilfoyle started dating Donald Trump Jr. and began campaigning for his father, her cosmetic coverage increased again. She also became a political mean girl. "No amount of drugs and makeup is going to make Joe Biden look good," she sneered on "The Joe Pags Show" ahead of the first 2024 presidential debate. But according to some social media critics, Guilfoyle is the last person who should be offering anyone makeup advice.

For a 2023 episode of "The Kimberly Guilfoyle Show," the titular host chatted with former Alaska governor Sarah Palin, who famously tried to appeal to moms like herself with a folksy quote about cosmetics. "What's the difference between a hockey mom and a pit bull? Lipstick," she said during the 2008 Republican National Convention, per the New York Post. While Palin loves some lip color, the former beauty queen might have advised Kimberly Guilfoyle to choose a different one if the host had asked for her input.

Guilfoyle buried herself in berry, coordinating her lipstick and blush with her outfit and her earrings. The sheer amount of vivid color was overwhelming because there's so much real estate on her lips, and this made it difficult to focus on the words coming out of them. "Gargoyle's magic marker makeup is too distracting — hard to focus on what she's saying," read one critique of her colorful countenance on X, formerly known as Twitter. This was likely not Guilfoyle's goal, as she had some important stuff to say to her listeners about Joe Biden's age. Referring to the president falling down, she cruelly joked, "He's better suited to be the spokesperson for Life Alert."

Guilfoyle's beauty look also included a generous amount of gunmetal gray eyeshadow slathered almost up to her eyebrows. But it was her pout that received the most biting criticism. "Did she use the whole lipstick at once?" another X user asked.

Kimberly Guilfoyle was in desperate need of some of Donald Trump's ear gauze to blot her face with when she chatted with Arizona Republican Kari Lake on "The Kimberly Guilfoyle Show." Guilfoyle looked a bit like she'd just taken a dip in a lake, but the spots on her T-zone that appeared to be damp could have been anything from sweat to face oil to highlighter that she got too heavy-handed with. Whatever the case, her glossy glam wasn't giving fresh and dewy.

Another issue with Guilfoyle's makeup was her fake eyelashes. They were so thick and long — like black sea urchin spines — that they appeared to be pulling her eyelids downward. The placement of her pink blush was also a bit off. She had smeared it too far from the apples of her cheeks, dragging it all the way to her nasolabial folds and making them more prominent.

The topic of Guilfoyle and Lake's conversation was how swell of a guy they think Donald Trump is. "I know that President Trump is willing to sacrifice everything," Lake said. Based on the dark lines around Guilfoyle's eyes and her severe brows, these sacrifices apparently included one of the Sharpie markers that are his preferred writing instruments. 

Forget a smoky eye — Kimberly Guilfoyle is all about that heavy char. One of her worst makeup instincts is to grab black eyeshadow and go to town with it, to the point that Gerard Way would say, "Girl, you're doing too much." The result of her head-scratching obsession with dark eye makeup is that she can look like her lids are being smothered by used oil. At least the harsh look is concordant with Donald Trump's "Drill, baby, drill" campaign messaging.

In the photo above, Guilfoyle could have used some of that superfluous facsimile of fossil fuel to fill in the sparse spots on her eyebrows. She needed to look her best, after all, as she was repping Donald Trump at the first GOP debate of 2023 in Milwaukee, Wisconsin. Donald did not show up to participate in the event, but Guilfoyle and Donald Trump Jr. were in attendance. The couple was hoping to mingle with the media in the spin room, but according to Donald Jr., they were not allowed to do so. "It shouldn't surprise any of us and it's also why Trump was 100% right to not go to this debate," he huffed, per the New York Post. No wonder Guilfoyle looks so downcast — or maybe that's just the weight of her falsies.

Donald Trump Jr. and Kimberly Guilfoyle decided to enjoy some fine dining at the upscale Japanese restaurant Zuma during a trip to London in 2024. However, Guilfoyle's eye makeup had a different craving — it made like Taco Bell and made a run for the border.

Guilfoyle seems to have no interest in even testing out a "less is more" approach to beauty, as she adopts the same smudged, charcoal eyeshadow no matter what the occasion. During her date with Trump, some of it had snuck below her lower lashline, ruining her entire beauty look by making it look messy. Unfortunately, dark makeup on the under-eye area has the added effect of mimicking under-eye circles, which results in a tired appearance.

Guilfoyle repeated another makeup mistake by going overboard with her rosy blush. There was so much of it that it looked like she had grabbed her compact and ground it into her cheeks raw rather than using a makeup brush. It also had a bright undertone that clashed with the more natural shade of pink on her lips. Her skin looked paler than usual, which worked fine with the pinks but made her dark eye makeup way too intense. 

Why Kimberly Guilfoyle's makeup went as wrong as it did when she joined Team Trump remains a mystery. However, Guilfoyle did get forced out of Fox News around the time she adopted her new go-to look. According to The New Yorker, other employees at the network had complained about Guilfoyle's alleged inappropriate behavior in the workplace. She was accused of showing her coworkers obscene photos and videos, and at least one makeup artist claimed that Guilfoyle would speak about sex in a vulgar manner.

HuffPost reported that Guilfoyle's exit from Fox News was due to the allegations against her, while her attorneys insisted this wasn't the case. Regardless, the result was that she lost access to the glam squad that came with the gig, and one insider told the Daily Beast that she had been using her makeup team outside of work. Her forced separation from the artists may help explain the "Mommie Dearest" eyebrows, Marie Antoinette blush, and caked-on foundation she sported at the 2024 Republican National Convention. Guilfoyle's eyelashes also looked like they were doing curls in the gym with weights they couldn't handle. "Does she have like 4 sets of false eyelashes on??" one X user asked. "Oh Kimberly what a mess, get the hell away from Trumps, they make you look like a Racoon," another tweet read.