Kimberly Guilfoyle's Makeup Style Has Completely Changed Between 2004 And 2024

Kimberly Guilfoyle's entire life may currently seem centered around her relationship with Donald Trump Jr., but her time in the spotlight predates that of the Trump heir. While the "Triggered" author became famous after joining his father's reality television show in 2004, Guilfoyle was already carving her own path as a famous attorney and wife to one of the most popular Democrats in the country.

Just three years into her marriage to Gavin Newsom, he was elected Mayor of San Francisco, making her the city's First Lady. If their marriage hadn't ended in 2006, Guilfoyle would have gone on to become California's First Lady when Newsom became governor. Instead, she moved to New York permanently and eventually switched political sides.

The 2004 and 2024 versions of Kimberly Guilfoyle are almost polar opposites. Although she's always been a fan of revealing outfits, everything else — from her values to her makeup style — has changed. Interestingly, the changes to her beauty routines seem connected with the switch in her personal life. However, unlike her political choices, her makeup evolution didn't happen overnight. In fact, without a side-by-side comparison, you might even miss the small but steady tweaks that made Kimberly Guilfoyle the figure we know today.

At the start of 2004, Kimberly Guilfoyle was already making waves in the legal world as a lawyer with the San Francisco District Attorney's Office. It had been two years since she gained international recognition for securing a murder indictment in a high-profile dog-mauling case, and her popularity didn't seem to be waning anytime soon. 

As a result, she was quite busy and, like many 9-to-5 women, seemed to favor simple and quick makeup routines that enhanced her looks but clearly didn't require hours in front of the mirror. Unlike her ensuing makeup styles, this wasn't too different from what Guilfoyle looks like without makeup. 

She stuck to simple brows, a touch of blush on the apples of her cheeks, and light, natural foundation — if she wore any at all. Most noticeably, her eye makeup was minimal, thanks to a little eyeliner and perhaps some mascara. The natural palette she used didn't scream "makeup expert," but it did highlight her striking eyes. The most daring part of the look is her pink lip.

By 2010, Kimberly Guilfoyle had experienced several changes. She'd left the courtroom to host Fox News' "The Lineup" in 2006 and divorced her second husband, Eric Villency, in 2009; it's no surprise that she made several beauty changes to transition from a busy 9-to-5 lawyer to a soft-glam television personality. Apart from dyeing her hair a darker shade, she began wearing her foundation a little thicker and arched her brows ever so slightly higher. Her blush remained light on her cheeks but seemed less like a natural flush.

One of the most noticeable changes was around her eyes. Unlike her earlier looks, Guilfoyle was clearly beginning her transition into her signature dark eye makeup. She wore a thicker layer of eyeliner along with more mascara or possibly a pair of false lashes. Despite these subtle changes, her look didn't appear overly artificial, and by 2011, the former attorney became a regular on the Fox network.

The year is 2016, and Kimberly Guilfoyle is now well-known in Republican circles. She has co-hosted "The Five" on Fox News for five years and officially switched from Blue to Red. She has also begun attending more GOP events and is even considered a potential candidate for Trump's press secretary.

Expectedly, as her popularity grew, so did her glam. She ditched the thin brows that had been trendy in the early 2000s and opted for thicker, more defined ones. Her blush became a heavy, rosy red shade, and her eye makeup was more intense than ever. She even fixed her powdery foundation look.

The former attorney also began using one of the oldest tricks in a makeup artist's book to look younger: using wider false lashes for a doll-eye makeup effect. This change may or may not have been influenced by her 2017 relationship with Don Jr. and their large age gap. Interestingly, Guilfoyle's makeup wasn't the only part of her that got bold. In 2018, the host was fired from Fox News for alleged sexual harassment.

At the start of the 2020s, Kimberly Guilfoyle's style transformation officially took a turn for the worse. Beyond her fashion choices, which featured increasingly inappropriate outfits, she officially stepped into the loud and unnatural makeup territory. She fully switched to a dramatic smokey eye, layering on heavy eyeshadow and bold eyeliner that made her eyes almost secondary to the makeup itself. Her lashes were thicker than ever, and her photos hinted at a switch to full-coverage foundation.

The former Fox News host also adopted a more bronzed and sculpted look. Around this time, she seemed to have gotten lip fillers and traded her signature side part for a center part. She even returned to a lighter hair color, resembling shades she wore earlier in her career. Unfortunately, her hair changes were trumped by her heavy makeup, which made her look peculiar — and not in a good way.

By 2024, Kimberly Guilfoyle's makeup took an even bolder and heavier turn. The soft, glamorous looks she once wore were long gone, replaced by a cakey foundation that appears unnatural. She stepped up her bronzer, applying it from her forehead to her cheeks. But it's not just the bronzer; every aspect of Guilfoyle's current makeup style is completely exaggerated, from her thick and poorly shaped brows to the odd color of her foundation.

However, one of the most criticized parts of Guilfoyle's current beauty routine is her eye makeup. She layers thick eyeshadow with winged eyeliner and bold lines along the top and bottom lash lines, finished off with heavy false lashes. The television host's eye makeup is so bold that it dominates her look, making it nearly impossible to see her actual eyes.

Unfortunately, this intense approach to makeup has erased all natural coloring from her face, creating an odd effect, which is probably why Guilfoyle's recent appearances feature makeup fails we can't ignore. And while everyone has the right to express themselves through their looks, it's fair to say this might be a great moment for her to consider hiring a new makeup artist.