Kimberly Guilfoyle's Beauty Evolution Went Off The Rails – Here's How Our MUA Would Fix It

Kimberly Guilfoyle has been a prominent figure within the MAGA crew ever since she paired up with Donald Trump Jr. in 2018 (the couple split in 2024), but she's been in the political realm for quite some time. Many may not recall that the current ambassador to Greece was once married to California Governor Gavin Newsom in the early aughts — and Kimberly Guilfoyle has had a complete transformation since then. Back then, she looked unrecognizable from her current self, and her makeup had a lot to do with it. Looking at her beauty evolution through the lens of a decade-long makeup artist, I can clearly see how her applications started going more and more astray.

Guilfoyle has always veered towards a soft glam, with heavily lined eyes and bright lipstick. However, her makeup has become heavier with time, and all her fillers aren't helping to soften up her face. Usually, folks learn to hone their skills over the years, but it looks like the former political commentator is just relying on packing on products to achieve that Republican makeup aesthetic.

With her love of cosmetics, it's hard to imagine what Kimberly Guilfoyle looks like makeup-free, especially when she loads on the products. In 2011, the political commentator had years of experience in broadcasting and worked as a co-host for Fox News. It's understandable that her choice of makeup was to go big, with heavily lined eyes, false lashes, and bright lipstick, as that's what many television personalities preferred at the time. During the mid-aughts, the trend was definitely more is more, and it looks like Guilfoyle ran with the theme.

Guilfoyle has strong features, which means too much makeup will just overpower her face. Her gorgeous blue eyes were hardly noticeable with all the heavy black eyeliner, which only made them appear smaller. The smoky eyes also fought with the bright cheeks and lips, which were plump enough without all the fillers Guilfoyle seemingly added later. Good makeup is all about balance and enhancing features, but Guilfoyle was all about applying everything, all at once. A focus on either her eyes or her lips would have looked much softer. 

2018 was the year Kimberly Guilfoyle began dating Donald Trump Jr., and she fit right in with the right-wing crowd. By then, her Republican makeup was in full effect, with loads of foundation and heavily drawn eyebrows, along with the requisite smoky eyes. Guilfoyle's blush blindness became even more apparent during this time, as her cheeks were packed with a bright pink shade that looked almost neon.

Guilfoyle toned down her heavily lined eyes with a more subtle look, which made them appear brighter. Still, the layers of foundation on her skin were way overkill, especially with the bright blush. With her warm undertone, a soft peach hue would have complemented her skin tone better, especially when paired with a bronzer to sculpt her cheekbones. During this time, Guilfoyle switched from bright lipstick to the nude color that her MAGA cohorts seem to favor, but at least the touch of gloss prevented her pout from looking overly flat.

Kimberly Guilfoyle's slightly toned-down makeup look didn't last too long, and the next year, she was seen with eyes smoked out to high heaven. Instead of drawing a sharp line, the right-wing commentator smudged the dark color around her peepers and then accentuated it with a grayish-brown eyeshadow. As if that wasn't dramatic enough, Guilfoyle added a pair of thick false lashes that further weighed down her eyes.

Unsurprisingly, Guilfoyle had on a full-coverage foundation, which was completely outdated. By 2019, the trend had shifted to a more natural, dewy look, instead of the heavy matte finish she prefers. And, it only drew attention to the fact that her shade was at least two steps lighter than her neck and chest, while being too cool for her undertone, to boot. A bit of liquid bronzer mixed into Guilfoyle's foundation would have done wonders for warming up her face, while diluting the heavy formula as well.

When you get to a certain age, less is more when it comes to makeup, as products tend to settle into fine lines and wrinkles. Eye makeup and foundation easily smudge due to hooded eyes and crepey skin, as is the case with Kimberly Guilfoyle. As someone who's nearing 60, she should focus on products that are designed for mature skin, such as a silicone-based primer that blurs wrinkles and pores. Then, a lightweight foundation with a silky finish would look best, as opposed to the matte formula she often uses.

Kimberly Guilfoyle's face has obviously transformed over the years, with her lips and cheeks plumped up for added volume. While that may have been done to make her appear more youthful, the dark eye makeup and strong brows add years to her face. Additionally, thick falsies were trendy about 10-15 years ago, but it's more about feathery lashes now. If she wants to add definition to her eyes, a lash lift and tint may be just the thing to give Guilfoyle the extra boost she needs, without having to look like she time-traveled from 2010.