Kimberly Guilfoyle’s Top Makeup Fails

Kimberly Guilfoyle’s beauty transformation over the years dramatically parallels changes in Donald Trump’s political views. Initially, Guilfoyle sported a more natural makeup look. However, as time went on, she began to indulge heavily in bronzer, mascara, and foundation.

During her marriage to California Governor Gavin Newsom, she exhibited a more restrained makeup style. This began to change when she joined “The Five” on Fox News. Her makeup became progressively heavier, with glossier lips, rimmed lash lines, and darker foundation tones. Journalist Jami Floyd commented on Fox’s beauty standards, saying, “It was Fox that changed everything: a Victoria’s Secret ethos driving what you look like on TV.” But this wasn’t the end of Guilfoyle’s evolving aesthetic.

With her involvement with Donald Trump Jr. and subsequent political campaigning, her makeup became even more intense. She also adopted a more combative persona, once remarking, “No amount of drugs and makeup is going to make Joe Biden look good.” This drew criticism, with many on social media suggesting she’s not one to give makeup advice.

For a 2023 episode of “The Kimberly Guilfoyle Show,” the host chatted with Sarah Palin, who famously quipped about lipstick during her 2008 vice-presidential run. However, Guilfoyle’s choice of lip color during this episode was a striking berry, coordinated with her entire outfit. The vivid color overwhelmed viewers, drawing comments like, “Gargoyle’s magic marker makeup is too distracting — hard to focus on what she’s saying.” Guilfoyle’s heavy gunmetal gray eyeshadow and striking lipstick drew significant criticism on social media.

During a conversation with Kari Lake on “The Kimberly Guilfoyle Show,” Guilfoyle appeared with a less-than-flawless makeup look. Her face had glossy spots on her T-zone, possibly from sweat, face oil, or highlighter. Her eyelashes were thick and long, almost dragging her eyelids down, and her blush was misplaced, accentuating her nasolabial folds.

The discussion focused on praising Donald Trump, with Lake saying, “I know that President Trump is willing to sacrifice everything.” However, viewers were distracted by Guilfoyle’s makeup, with some commenting on her dark eyeliner and severe brows.

Guilfoyle’s tendency to opt for dark, heavy eye makeup often results in a dramatic, sometimes overly intense look. At the 2023 GOP debate in Milwaukee, her dark eyeshadow and sparse eyebrows drew significant attention. Guilfoyle and Donald Trump Jr. attended the debate, but were not allowed to mingle in the media spin room, leading Donald Jr. to comment, “It shouldn’t surprise any of us and it’s also why Trump was 100% right to not go to this debate.” Guilfoyle’s downcast appearance may have been due to the situation or the weight of her falsies.

During a 2024 date night at Zuma in London, Guilfoyle’s eye makeup seemed to be migrating. Her signature smudged, charcoal eyeshadow had snuck below her lower lash line, creating a messy look that resembled under-eye circles. She also applied too much rosy blush, which appeared almost raw on her cheeks and clashed with her more natural lip color.

The reasons behind Guilfoyle’s drastic makeup changes during her time with Team Trump remain unclear. She was forced out of Fox News due to allegations of inappropriate behavior and lost access to the network’s makeup team. Without professional help, she appeared at the 2024 Republican National Convention with overly harsh eyebrows, intense blush, and heavy foundation.

Her eyelashes looked like they were laboring under excessive weight, with critics on social media asking if she had multiple sets of false eyelashes on. One user commented, “Oh Kimberly what a mess, get the hell away from Trumps, they make you look like a Racoon.”