In 2025, The Daily Beast printed a bit hinting that Kimberly Guilfoyle, amongst different ladies within the Trump authorities, had modified her sense of favor out of some kind of loyalty to President Donald Trump and his marketing campaign. In a bit titled, “Usha Vance is about to remodel right into a Trumpian trad spouse,” author, Joanna Coles, described the methods during which a number of ladies had reworked their appears to be like in response to their relationships to completely different males throughout the Trump empire. Apparently, Guilfoyle was one such lady. In spite of everything, she dated Donald Trump Jr., and because the article states, “Guilfoyle was as soon as a lawyer, too. Now she’s a Republican adviser with tunnel cleavage and heavy darkish eye make-up that might make even Cleopatra say, ‘Honey, maintain the kohl.'”

Whereas this story of Kimberly Guilfoyle’s Trumpian fashion transformation could also be tempting to consider, the truth is definitely rather more difficult than that. In reality, Guilfoyle embraced beauty-queen make-up lengthy earlier than she met Donald Trump Jr. She might need even undergone a number of surgical enhancements nearly a decade earlier than the “Make America Nice Once more” motion even existed. Though it’s true that Guilfoyle has modified her face quite a bit over time, it appears that evidently this transformation has occurred in tandem together with her skilled evolution relatively than her relationships. From her time as a public determine in San Francisco to her tenure as a media guide to a nominee for the American ambassador to Greece, Guilfoyle has allowed her face to replicate her place. 

Nowadays, Kimberly Guilfoyle is called a former Fox Information media persona, Donald Trump Jr.’s ex-girlfriend, and President Donald Trump’s choose as ambassador to Greece. However again within the late Nineteen Sixties, she was an cute child who was beloved by her dad and mom. Certainly, across the time of her delivery in March 1969, the long run media persona’s mom, Mercedes Gerena, and her father, Anthony Guilfoyle, splurged on a proper household picture. The shot — which Kimberly later shared on Instagram — exhibits the proud dad and mom staring on the digicam with their child on Mercedes’ lap. Kimberly was, in fact, as cute as a button with spherical cheeks and a full head of hair. Her face reveals a specific amount of curiosity as she stares on the digicam.

Though it is onerous to take a look at this outdated picture and picture the stunning transformation that Kimberly Guilfoyle would in the future endure, it’s simple to pinpoint the resemblance between the general public determine and her mom. Like Kimberly, Mercedes boasted full lips and a sq. jaw. Her mom additionally had outstanding cheekbones that had been clearly handed all the way down to her daughter. Though Kimberly Guilfoyle has long inspired plastic surgery rumors, her mom’s traits present that lots of her options had been really inherited down the maternal line. 

Though the grownup Kimberly Guilfoyle appears to be like an entire lot like her mom, the younger Guilfoyle really took after her father. Grainy household photographs from the Seventies present that the media persona resembled her dad in additional methods than one. In an outdated childhood image posted on Guilfoyle’s Instagram, she’s hugging her father and smiling on the digicam. The cheek-to-cheek shot exhibits that Guilfoyle inherited her pointy nostril and shiny smile from her expensive outdated man.

Curiously, a household resemblance will not be the one factor that the media persona received from the paternal aspect of her household. Guilfoyle’s mom died when she was solely 10 years outdated. Subsequently, her father stepped up and raised her alone. As Guilfoyle shared within the caption of the aforementioned Instagram publish, “After we misplaced her, you raised Anthony and me with limitless love and power … You may at all times be my hero.”

In the course of the years when Guilfoyle was cared for by her father, she watched him go down a few of his most beloved values. These included bravery, braveness, and patriotism — beliefs that Guilfoyle says she follows to this present day. As she shared within the caption of a separate Instagram publish, “From an early age, my father impressed and taught me to at all times get up for myself, my values and my nation. I nonetheless bear in mind my father saying: Be extra afraid of the concern that hinders [you] than the concern of asking, at all times be your finest advocate.”

As Kimberly Guilfoyle moved into her grownup years, her life modified fully. Whereas finishing her undergraduate diploma on the College of California, Davis, she realized that she wished to grow to be a lawyer. Though she was accepted into the College of San Francisco College of Regulation, Guilfoyle’s future within the authorized world was removed from assured. In spite of everything, her tuition and residing bills weren’t precisely free. Motivated to make ends meet, Guilfoyle determined to attempt her hand at modeling. As she would later inform People, “I knew I wished to go to regulation faculty and it ended up being a good way to pay for it. I modeled the whole lot from garments, swimwear and lingerie, together with Victoria’s Secret!”

Though the modeling world has the fame for emphasizing make-up and cosmetic surgery, Guilfoyle apparently averted these enhancers throughout her early profession. She even posted an outdated headshot on Instagram — revealing that she was accustomed to embracing an all-natural, makeup-free look. 

Due to this, her face regarded younger, recent, and completely clear. Reflecting on today with Folks, Guilfoyle remembered the teachings she realized, not simply the garments she wore. “I met an unimaginable variety of attention-grabbing individuals by way of modeling and actually realized quite a bit about self-confidence and self-worth,” she defined.

Kimberly Guilfoyle might have averted make-up in her outdated modeling headshots, however that does not imply she maintained this pure search for lengthy. After graduating from regulation faculty, she selected to enter public life, first as a prosecutor in San Francisco and ultimately an Assistant District Legal professional. Throughout this time, she fell in love with future Governor of California Gavin Newsom, who was then hoping to grow to be the mayor of San Francisco. The pair walked down the aisle in 2001, and Newsom turned mayor three years later — making Guilfoyle the primary woman of San Francisco.

For Guilfoyle, taking up these roles within the public eye was a very huge deal. Now not was she a typical regulation pupil — she was an necessary political determine. As such, photographs present Guilfoyle sporting refined, first-lady make-up throughout this time interval. One shot exhibits her at a celebration with Newsom. On this event, she dressed up her look with easy eyeshadow, lipstick, lip gloss, and a strong layer of basis. As a lot effort as Guilfoyle invested into her face, nonetheless, she was recognized for her persona. Newsom himself advised SFGate in 2001, “I can even say that Kimberly is the one individual I’ve ever recognized in my life who will get increasingly enticing with day-after-day that passes. And that comes from inside, clearly.”

Simply because Kimberly Guilfoyle took on a public function throughout her tenure within the district legal professional’s workplace doesn’t suggest that she at all times went for probably the most glamorous appears to be like. In 2004, she attended a number of occasions in what seemed to be semi-professional apparel. This was very true on the GLAAD Media Awards in New York Metropolis. For this occasion, she wore a strappy black gown that stored issues cool. Her face matched the general really feel of her look as she wore an cute pair of glasses on the podium.

Though the selection to put on glasses or not could appear small, framing your face with a pair of spectacles can totally rework the best way others understand you. Writing for Psychology Today, Susan Krauss Whitbourne, PhD, ABPP, defined that this accent actually can make you look smarter. “Folks with glasses appear to be they learn extra; therefore, they’re [viewed as] extra clever,” the knowledgeable shared. Whitbourne additionally famous that glasses can impression the best way others understand your ethical character, writing, “You could look extra reliable in case you’re sporting glasses with rims.” In that sense, Guilfoyle’s alternative of accent would have framed her face in a method that was useful for her political profession. Not solely did her glasses make her look sharper, however additionally they made her look like a extra moral individual.

Though Kimberly Guilfoyle and Gavin Newsom remained married for a time, the political energy couple was not meant to final. The pair divorced in 2006 and Guilfoyle went on to marry Eric Villency that very Could. Simply 5 months after tying the knot in a romantic Barbados ceremony, Villency and Guilfoyle welcomed their son, Ronan Villency, in 2006. Shortly after giving delivery, Kimberly Guilfoyle rocked a rare no-makeup look that enhanced her magnificence in a throwback picture she posted on social media.

As revealed in a photograph of this second — which Guilfoyle later shared on Instagram — the media persona apparently stored her face fully pure. She wore no seen eyeliner or eyeshadow, and the small freckles that we will see on her cheeks counsel that she forewent basis as effectively. This picture exhibits that Guilfoyle didn’t gown up her countenance for these first few moments of maternity. As an alternative, she determined to spend that point bonding together with her new son.

The beginnings of Kimberly Guilfoyle’s profession might have been marked by various pure appears to be like, however that does not imply she embraced these for lengthy. In 2005, Guilfoyle started internet hosting “Each Sides” on CourtTV — permitting her to remodel from a political determine to a media one. As Guilfoyle started to spend increasingly time in entrance of the cameras, rumors of potential plastic surgical procedures started to pop up throughout her. To unravel the rumour, The Record reached out to Dr. Raja Mohan, a board-certified plastic surgeon based mostly in Dallas, Texas. Based mostly on what Dr. Mohan advised us, it is very potential that Guilfoyle underwent just a few procedures round this time.

Pointing to {a photograph} of Guilfoyle on the premiere of the 2007 movie “Sleuth” in New York Metropolis, the surgeon advised us, “Probably the most notable variations seem within the contour of the jawline and neck, that are sharper and extra outlined … This may be achieved by way of a decrease facelift or neck carry, typically mixed with liposuction underneath the chin to take away extra fats and tighten the pores and skin.” In different phrases, Guilfoyle doubtlessly sought surgical interventions to assist her obtain a youthful look. She additionally appeared to extend the quantity of make-up on her face, making use of copious quantities of black eyeliner and a very shiny model of lipgloss. 

As Kimberly Guilfoyle’s media profession took off, she piled extra make-up on. In 2011, the previous Democratic first woman of San Francisco began as a co-host of the Fox Information night present, “The 5,” having been with the community since 2006. Maybe as a result of she was spending extra time in entrance of the cameras, Guilfoyle’s appears to be like grew more and more makeup-heavy. Though her period of dramatic beauty procedures was nonetheless just a few years away, by 2012, Guilfoyle’s make-up had already taken on a daring and heavy-handed aptitude. She typically appeared with overly vivid touches — flushed bright-pink cheeks, darkish eyeliner, shiny lips pushed to extra, and brows darkened with a heavy sweep of powder. The general impact very a lot referred to as to thoughts a magnificence queen.

Curiously, it was on this similar yr that journalist Liza Mundy printed a report in The Atlantic discussing the sweetness requirements imposed on feminine anchors for Fox. In her write-up, Mundy reported, “A Fox common as soon as commented to me that she will get extra calls from community administration about her hair, garments, and make-up than about what she says. ‘I simply consider it as a uniform,’ [the journalist] mentioned of her getup.” Though it is unclear whether or not or not Guilfoyle felt any type of stress to stick to those requirements, you will need to contemplate that she was working in a spot with an unstated makeup-heavy rule on the time that she upped her glam.

By the point 2018 got here round, Kimberly Guilfoyle was one of many largest names at Fox. She additionally seemed to be married to her makeup-heavy look — displaying up at quite a few occasions with what appeared to be a number of layers of basis caked onto her pores and skin. Though she did depart her tv function later that yr, Guilfoyle continued to seem within the public eye. That yr, she even traveled to Bozeman, Montana, to assist then-Republican candidate Matt Rosendale in his bid for the Senate. Shut-ups of Guilfoyle’s face at Rosendale’s marketing campaign occasions present she was sporting loads of blush, eyeliner, and eyeshadow. These similar pictures additionally revealed that her cheeks and brow lacked the quantity of plasticity usually seen in unaltered pores and skin.

To know why Guilfoyle’s face regarded so frozen, we spoke to Dallas-based board-certified plastic surgeon Dr. Raja Mohan. After inspecting one of many photographs of Guilfoyle’s Montana journey, the medical knowledgeable posited, “A stiff facial look is usually the results of overuse of Botox and fillers. In Kimberly Guilfoyle’s case, heavy Botox within the brow and across the eyes, paired with substantial filler within the cheeks, lips, and jawline, can cut back pure motion and create a mask-like impact.” Curiously, Dr. Mohan additionally concluded that Guilfoyle’s make-up may even contribute to this overly clean look. “Extra quantity, mixed with heavy make-up or picture retouching, can additional exaggerate stiffness,” Dr. Mohan advised The Record.

Kimberly Guilfoyle’s face will not be the one factor that modified in 2018. Throughout that yr, Guilfoyle initiated a relationship with President Donald Trump’s son, Donald Trump Jr. Though Guilfoyle and Don Jr. would break up in 2024, there was a time when the 2 appeared destined to final. Previous to their break up, the couple really had plans to wed.

Fascinatingly, it was throughout her relationship with Don Jr. that Guilfoyle underwent yet one more bodily transformation. She started to appear in public with lips that appeared bigger than ever earlier than. This was particularly evident in a video shared to Guilfoyle’s Instagram in Could 2024. The footage — which captured Guilfoyle talking — emphasised the dimensions of her mouth.

Commenting on this in an unique dialog with The Record, Dr. Raja Mohan attributed Guilfoyle’s transformation to fillers. “Kimberly Guilfoyle’s lips present indicators of great enhancement, most probably from hyaluronic acid–based mostly dermal fillers. The amount seems evenly distributed all through each the higher and decrease lips, with added definition alongside the vermillion border and cupid’s bow,” Dr. Mohan advised us. Within the surgeon’s opinion, Guilfoyle might have undergone a number of procedures, stopping her from shifting her lips naturally. “When filler is layered over time, it may result in a firmer look and diminished flexibility, which can clarify why her lips transfer in a extra restricted method when she talks,” defined Dr. Mohan.

In 2025, Kimberly Guilfoyle started a brand new section in her profession after being nominated by President Donald Trump a yr earlier than because the U.S. ambassador to Greece. Though she has lengthy been recognized for sporting oodles of make-up and pageant-worthy hairstyles, Guilfoyle appeared to ever so barely tone down her look to replicate her potential new function, simply one of many many times Kimberly Guilfoyle tried to look professional but failed miserably.

This was evident on July 9 when she appeared earlier than the Senate International Relations Committee on Capitol Hill throughout a nominations listening to and was requested questions on Greece’s relationship with Turkey. As evidenced by her look on the day, Guilfoyle appeared to have taken a small break from some points of the daring make-up she’s worn up to now, as a substitute sporting a impartial shade of lipstick and a extra refined shade of blush. Though her eye make-up was darkish and heavy, she wore glasses, presumably hinting at her need to be seen as an clever, ethical determine. 

This main transition in how Guilfoyle presents her face to the general public demonstrates her capability to shift her picture based mostly on completely different skilled conditions. Whereas she adopted a extra pure look throughout her tenure in San Francisco politics, Guilfoyle leaned into the beauty-queen fashion throughout her time at Fox Information. When she dated Donald Trump Jr., Guilfoyle’s look turned extra artificially enhanced. In 2025, although, as a potential ambassador, Guilfoyle’s face modified as soon as extra.