Kimberly Guilfoyle’s Most Embarrassing Makeup Moments

Kimberly Guilfoyle has long been a controversial figure, but recently, it’s her over-the-top makeup looks that have been getting the most attention. From her bronzed foundation to dramatic eye makeup, Guilfoyle’s beauty transformations have sparked more than a few eyebrows. Known for her role as a political commentator and for dating Donald Trump Jr., Guilfoyle’s look has evolved—sometimes for the better, and sometimes, not so much.

Here’s a look at some of her most embarrassing maTkeup moments over the years that have left fans buzzing.

Lip Color Failin’ with Palin

During a 2023 episode of The Kimberly Guilfoyle Show, she had a conversation with former Alaska governor Sarah Palin, who had made headlines for her famous “lipstick” quote during the 2008 Republican National Convention. However, Guilfoyle took it a step too far, going overboard with berry-colored lipstick and blush, which clashed with her outfit and jewelry. The vibrant hues overwhelmed her face, distracting from what she was saying.

One viewer on X (formerly Twitter) quipped, “Gargoyle’s magic marker makeup is too distracting — hard to focus on what she’s saying.” Others wondered if she had used the entire lipstick in one sitting, as her lips appeared to be completely caked in the product.

The Wet Look With Kari Lake

Another memorable moment occurred when Guilfoyle interviewed Arizona Republican Kari Lake on her show. Fans noted that her face appeared as if she’d just come from a swimming pool, with spots on her T-zone that looked either like sweat or an overzealous application of highlighter. In addition, her fake eyelashes were so thick that they seemed to pull her eyelids downward, giving her a tired or strained look.

Her heavy-handed application of pink blush made the situation worse, as she smeared it too far beyond the apples of her cheeks, emphasizing the lines around her face. The overall result? A makeup disaster that failed to convey the polished image she likely intended.

Channeling Texas Tea in Old Milwaukee

Kimberly Guilfoyle’s obsession with dark, smoky eye makeup has often led to disastrous results. In one notable appearance at the first GOP debate in Milwaukee in 2023, her dark eyeshadow was so heavy and smeared that it made her look like she had been dunked in oil. Her makeup looked more suited for a goth rocker than a political spokesperson, and her overly charred eye makeup drew comparisons to an overcooked barbecue, with one fan suggesting that Donald Trump’s “Drill, baby, drill” campaign was the inspiration for her look.

Despite the harsh appearance of her makeup, it was clear that Guilfoyle had gone for an extreme aesthetic, perhaps trying too hard to fit in with the bombastic political image she was cultivating.

Migrating Makeup on Date Night

Even during a romantic evening out with Donald Trump Jr. in London, Guilfoyle’s makeup didn’t quite cooperate. While dining at the upscale Japanese restaurant Zuma, her eye makeup migrated below her lower lashline, resulting in a messy look. The smudged charcoal eyeshadow under her eyes gave the illusion of tiredness, resembling under-eye circles rather than a polished, fresh appearance.

Additionally, her blush was applied so heavily that it looked as if she had rubbed it into her cheeks rather than gently applying it with a brush. The too-rosy blush clashed with her bright lipstick, making her complexion look pale and out of balance.

A Mishap at the 2024 Republican National Convention

Kimberly Guilfoyle’s appearance at the 2024 Republican National Convention was another example of her overdone makeup. Without access to her usual glam squad from Fox News, which she reportedly lost access to after her departure from the network, Guilfoyle’s makeup appeared excessively heavy-handed. Her foundation was cakey, her eyebrows appeared drawn on with a sharpie, and her lashes looked like they were struggling under the weight of several sets of false eyelashes.

The overall effect was jarring, with fans on social media commenting on her “Mommie Dearest” eyebrows and exaggerated makeup. One X user even asked, “Does she have like 4 sets of false eyelashes on??” Another tweet read, “Oh Kimberly, what a mess, get the hell away from Trumps, they make you look like a raccoon.”

Conclusion

While Kimberly Guilfoyle’s style has certainly evolved over the years, not all of her makeup choices have been a hit. From her over-application of bronzer and lipstick to the infamous heavy eye makeup, her beauty moments have often overshadowed her political commentary. Whether it’s her attempt to channel a dramatic image or simply pushing the boundaries of glam, Guilfoyle’s makeup choices have become just as much a part of her public persona as her political views.

Despite the criticism, one thing is clear: Kimberly Guilfoyle is unafraid to experiment with her look, even if it occasionally results in a makeup disaster. Perhaps her next beauty evolution will find a balance between bold and polished—but for now, fans will continue to watch her beauty missteps with both fascination and amusement.