Kimberly Guilfoyle Has Undergone A Dramatic Transformation Since Her First Divorce

Kimberly Guilfoyle split from her first husband, the divisive politician Gavin Newsom (who has some strange things in his second marriage to Jennifer Siebel), in 2005. "Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple," they said in a joint statement (via SFGate). "Over the past 10 years, we have developed a tremendous bond of love and respect for each other. That will never change," they added. The twosome's divorce was finalized the following year, and Guilfoyle has undergone a serious transformation since being known as Mrs. Newsom.

Not only has her life changed drastically (she joined and left Fox News, got engaged and split with Donald Trump Jr., and was sworn in as the next U.S. Ambassador to Greece) the Guilfoyle also looks nearly unrecognizable since she and Newsom went their separate ways. To see how far she's come, we're looking back at her ever-evolving appearance. And, yes, that includes the omnipresent plastic surgery rumors that have plagued her career.

Post 2020, Kimberly Guilfoyle is nearly unrecognizable without her hair extensions, but there was a time where she rocked shorter tresses. in this photo from Marc Jacobs fashion show in 2006, the forthright republican can be seen with a shoulder-length cut and side part that gave her a youthful, fresh appearance. At the time, she was in her late thirties, dating Eric Villency, and pregnant with her her son Ronan. During this era, she appeared to be going with a much lighter makeup look, as her face didn't appear to have any signs of heavy contour or overlined lips.

In 2008, Kimberly Guilfoyle started to morph into a version of herself closer to the one we've seen in the 2020s. She'd seemingly discovered hair extensions while attending a screening of the movie "August." Her mane was a little longer and much fuller than before. She wore it in a dramatic side part and created serious height around her crown, suggesting she'd had extensions installed for volume rather than length. The star's face was also more chiseled, which could have been down to post-pregnancy weight loss.

Kimberly Guilfoyle had a noticeably more glam look by 2010. Having split with Eric Villency the previous year, the Fox News personality got her second post-divorce glow. She made a serious statement and gave us Taylor Swift-esque revenge dress vibes when she attended the screening of "The Sorcerer's Apprentice" in a hot pink cocktail dress with a deep, healthy-looking tan. Her glossy, long locks cascading over her shoulder, her skin looked super smooth, and she expertly matched her manicure to her flirty dress shade.

By 2011, Kimberly Guilfoyle had landed herself a more prominent role on Fox News as a co-host on the talk show "The Five" and consequently, her style shifted to fit with her new gig. She served up the classic overly made-up aesthetic with heavy contouring and began dressing in more corporate appropriate attire. Her hair was longer than ever with obvious extensions, and she was regularly spotted with a glossy lip that glistened in the on-set lighting.

By 2014, Kimberly Guilfoyle looked drastically different from her 2006 self. While attending a charity gala, the then-Fox News personality wore long, faux lashes and had full, glossy lips. Her face also appeared slimmer, which was likely achieved via carefully placed contouring and blush. Despite being in her forties, she wasn't showing obvious signs of deep wrinkles on her forehead either, which board-certified plastic surgeon Dr. Dennis Schimpf speculated could have been Botox-related. "I think initially she started out with Botox to her forehead, crow's feet around her eyes, and glabella area," he told Glam, though Guilfoyle's never confirmed getting the injection.

Kimberly Guilfoyle departed Fox News in 2018 but had more eyes on her than ever before thanks to her newfound romance with Donald Trump Jr. When the pair attended a premiere together, she looked so different than when she was with Gavin Newsom. Her dark caramel highlighted hair was super long and in soft waves, and she ditched bright lipsticks in favor of glossy, nude lip gloss. Guilfoyle embraced spicy fashion too, wearing a form-fitting white dress that was anything but subtle to ensure all eyes were on her.

When Kimberly Guilfoyle stepped out for a Mira Zwillinger fashion show in 2020 she looked closer to a reality star than a politician. Clad in a bright yellow blouse, with warm brown hair extensions and light pink blush, we'd have guessed she was headed to be on "Love Island." Following this appearance, there was plenty of speculation she could have undergone cosmetic procedures. "Her cheeks and lips have maintained a fullness that's most likely from filler or fat grafting," board-certified plastic surgeon Dr. Sean McNally purported to Daily Mail, though Guilfoyle has never confirmed the plastic surgery chatter.

In 2023, Kimberly Guilfoyle landed her own, short-lived, online show called "The Kimberly Guilfoyle Show," and she took her signature heavy makeup to a whole new level. She was repeatedly seen very heavily made up (even more so than on Fox News) and often sported super smoky eyes, heavy blush, and obvious lipstick with overly-lined lips, all at the same time. Fans took notice of her heavy approach to cosmetics, with one X user writing, "What the hell is up with Kimberly Guilfoyle's makeup."

In 2025, the newly single Kimberly Guilfoyle was officially sworn in as U.S. Ambassador to Greece. Soon, we saw the politician adopt a more sophisticated wardrobe, seemingly to match her important new role. This included the white pussybow blouse and black blazer look she wore to a meeting with the Senate Foreign Relations Committee. The look was no doubt striking and clearly indicated that Guilfoyle had long evolved from her days of wearing fitted pink dresses. That said, it was impossible for some to not take note of how different her face appeared compared to photos from the previous year. Dr. Dennis Schimpf even recommended to Glam that she dissolve any filler she may have gotten. "To give her a more natural appearance," he said.