At this point, you couldn't ignore Kimberly Guilfoyle if you wanted to. Over the years, she has become a fierce MAGA force you don't want to reckon with, commanding attention both on and off screen. But beyond her outspoken, proud-to-be MAGA presence, it's honestly the striking evolution of her face that probably has people talking most. From her early days, where she gave modeling a shot, to her feather-like lash extension and severely smokey-eyed makeup era, standing beside Donald Trump Jr. in every
MAGA photo-op (the two separated in 2024), it's clear Guilfoyle doesn't like obscurity.
While she's never confirmed how she did it, she's had a complete face transformation that's seriously impossible to ignore. Her lips have become noticeably fuller, and her face overall looks far less natural than it once did, with expressions that don't quite move the way they used to. And let's be real, if she were to say it's simply due to her aging, we doubt many people would buy that.
We're just bummed because her natural beauty and image-making used to be her strong suit, but her current look is stirring the pot and sparks far more speculation than compliments and admiration—even her fans can't seem to help but comment on her photos, urging her to embrace a more natural appearance. Whether you love her or hate her, her face transformation is impossible for anyone to ignore.
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Her Jaw-Dropping Naturally Gorgeous Modeling Days
Long before her days as a MAGA spokesperson, Kimberly Guilfoyle was turning heads in all of the right ways as a young model in the 1980s. While it's unclear how successful her modeling career was, the photos of her prove she had the most naturally radiant features and effortless beauty, and gave the strongest laid-back California girl vibes. She had a seriously undeniable presence that must've been impossible to ignore. Guilfoyle must reminisce on those days often, too, as she'll occasionally share throwback photos like this one on her social media platforms leaving fans to swoon over her glamorous 20s.
She Gave Julia Roberts Vibes During Her Time As The First Lady Of San Francisco
Believe it or not, in the early 2000s, Kimberly Guilfoyle was open-minded enough to attend events hosted by the National Center of LGBTQ rights—back when she was the First Lady of San Francisco and also Gavin Newsom's wife. Despite the 20-year difference, she was no less beautiful than in her modeling days. Her natural features were glowing, and her makeup was perfectly understated, highlighting her best features. Fast forward to today, Guilfoyle's got a completely transformed face, claims she's always been conservative, and she's throwing shady digs at her ex-husband whenever she has the chance.
Her Pregnancy Glow Was Absolutely Surreal
Kimberly Guilfoyle was pregnant and gave birth to her first and only child in 2007 with her second husband, Eric Villency. Even while expecting, she had that classic pregnancy glow, and her natural features were front and center. Clearly, she's always had serious discipline, as her lean figure barely hinted at the pregnancy, if it weren't for the baby bump. She radiated that effortless beauty, looking soft and natural in a way that's miles away from the high-glam, camera-ready look she sports these days.
Second Divorce Who?
Only three years into her second marriage, Kimberly Guilfoyle signed divorce papers, again. Yet heartbreak and motherhood had nothing on this lady. Despite the peril in her personal life, Guilfoyle was up and running around the social scene with almost no downtime, and we can't blame her. She looked absolutely stunning in 2010. Whether it be her figure or her face, she looked remarkably similar to her pre-mom self, but there is one thing we can't help but notice. It seems this is where she began experimenting with her makeup, as you can see she's sporting a more familiar tan, cheeks that some may consider too pink, and a light, but very much prominent smokey eye.
A Plumped-Up Smile Amid Scandal
2018 was one heck of a year for Kimberly Guilfoyle, but you couldn't even tell with all of the events in NYC she continued to attend. At the celebration of a restaurant opening, she showed off a deeper tan than the previous years, unnaturally full cheeks, plumper lips, and lifted brows. Meanwhile, when she left Fox News, the company was investigating allegations of her abusive behavior towards an assistant. Yet there she was, at all social events, smiling for the cameras, seemingly untouched by the chaos that ensued behind the scenes. We guess you could say she's very good at leaving work in the workplace.
A New Romance Blossoms, And Does A New Look
Call it a coincidence, but a few years into dating Donald Trump Jr. in 2019, Kimberly Guilfoyle's face started to look noticeably different. Not only was her makeup heavier, but she also had fuller cheeks and a more sculpted look that slowly began to define her appearance. In fact, board-certified plastic surgeon, Dr. Dennis Schimpf spoke to Glam and suggested she may have started with a little bit of Botox here and there to combat signs of aging. Still, she didn't look too unnatural. If anything, her refreshed appearance injected a bit of youth and highlighted her naturally strong features.
From Natural Beauty To More Defined
By the year 2020, Kimberly Guilfoyle's face showed a ton of noticeable changes. First of all, her makeup was completely different. She started wearing feather-like lash extensions paired with a heavy, smokey eye and overly blushed cheeks that have now become her signature makeup look. But what stood out most was her once slim, elongated face looked rounder with much fuller cheeks. In the interview with Glam, Dr. Dennis Schimpf carefully suggested that at some point she may have started adding fillers to her routine.
When People Started Comparing Her Smile To The Joker's
Only a year after the previous photo, Kimberly Guilfoyle posted a selfie with her son on Facebook—and some fans couldn't help but notice her smile looked different. One fan was too blunt as they commented, "What happened to your face? Good god." It must've looked bad to many because people couldn't help but compare her to the Joker. While there were no confirmations on what caused the stark change, it was clear her facial transformations, along with her makeup, were becoming more pronounced than ever.
Showed Up To A Trump Family Christmas In Full Glam
When Christmas 2022 came around, Kimberly Guilfoyle no longer really looked like the woman everyone remembered. Her smile was wider, and even in a photo, it was obvious her face wasn't moving as naturally. And we can't help but think how many heads she turned for her over-the-top look at a Trump family Christmas party. While everyone else, even the kids, were dressed fairly casually, Guilfoyle showed up looking like she was heading to a gala — statement drop-style earrings, an overly embellished dress, a full face of make-up, and a fresh blowout. Family time or not, she's not one for blending in.
She Loves Herself No Matter What
Kimberly Guilfoyle must have really been feeling herself in December 2023, as she posted multiple photos of what appears to be a glam photoshoot of none other than herself. But with every shot she shared, concerned fans flooded the comments, pleading with her to ease up on facial enhancements. One fan said, "Kimberly, you are beautiful. But please please stop with the lip fillers," then another said, "Too much BOTOX." One individual even compared her to Morticia Addams. Yikes. This really highlighted just how much people thought her face had changed and underscored the growing concern over her continually evolving look.
The Signature Mar-A-Lago Face We Know Today
And finally, we've reached Kimberly Guilfoyle present-day — perhaps the face and overall look the majority of us recognize today. Critics often say she is the perfect representation of the Mar-a-Lago face: very high, firm, and overfilled cheeks, taut skin in which pores are non-existent from thick layers of makeup, a sculpted jawline, and teeth so white they glow. Alongside the facial changes, her fitted mini baby pink dress highlights a noticeably slimmer frame compared to photos from previous years, with the weight loss only sharpening the overall chiseled effect.
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