Kimberly Guilfoyle's Sharpie Eyeliner Was So Black, It Cast Its Own Shadow Over Don Jr.

Kimberly Guilfoyle isn't known for her subtlety, either when delivering loud, bombastic speeches or when it comes to her makeup. Specifically, she's notorious for her dark, heavy-handed eyeliner and eyeshadow choices that look like she's taking style inspo from a particularly glam raccoon. Looking back on past years and her time in the political spotlight, it's clear that Guilfoyle's makeup style has completely changed over the past two decades, with her look getting much darker, bolder, and more dramatic.

However, back in April 2024, before Guilfoyle called off her engagement to Donald Trump Jr., she and her then-fiancé shared a date night at the Wags To Riches Gala in Palm Beach, Florida. Guilfoyle took to Instagram at the time to share a slideshow of snapshots from the event, but it was her over-the-top Sharpie eyeliner that really stole the spotlight. The moody makeup choice was contrasted by her canary yellow, semi-sheer gown and brought a real theatricality to the look.

The eyeliner was a darker shade of jet black than Trump Jr.'s boring suit, and made him look reserved and almost modest by comparison. This appearance at the event — which benefitted Furry Friends Humane, a no-kill animal shelter in Jupiter, Florida – was just one of many appearances Guilfoyle has made in recent years in which she's shown off her love for heavy eyeliner – as well as her love for sharing some heavily edited Instagram pics, if we're being honest.

Over the past few years, Kimberly Guilfoyle has made countless make-up mistakes that are too obvious to ignore. From cakey foundation to brooding, vampy looks that made her stick out like a sore thumb in a crowd, it's clear that Guilfoyle has been seduced by the dark (make-up) side. Although this wasn't always the case. Simply looking back to her modeling days shows just how much of a style transformation she's undergone since stepping into the public spotlight.

Back in the early 2000s, Guilfoyle embraced her natural beauty and gave off rom-com movie star vibes while married to the future governor of California, Gavin Newsom, who, for the record, has aged like fine wine over the last 20 years, following his divorce from Guilfoyle in 2005. However, things began to change radically when it came to her looks around the time she began her relationship with Donald Trump Jr.

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Specifically, critics and commentators often point to Guilfoyle as a perfect example of the so-called "Mar-A-Lago Face" cosmetic surgery trend. Plastic surgeon Dr. Faryan Jalalabadi spoke about the phenomenon with The Independent in April 2025, and said it usually refers to women who are trying to obtain "the tiny little pixie nose and big lips." Jalalabadi explained the trend is all about creating a look that is "the opposite of a natural face, in which there's a delicate balance of proportions." While surgery and cosmetic procedure claims regarding Guilfoyle have not been confirmed, there's very little question that she's definitely buying her eyeliner and eyeshadow in bulk.