From the courtroom to the political stage, the news personality’s appearance has evolved dramatically over the years, sparking both admiration and criticism from fans.
Kimberly Guilfoyle, once a San Francisco prosecutor and Fox News personality, has undergone a striking transformation throughout her public career.
Her appearances in the last few years have revealed a look vastly different from her early days in law and media, drawing comments from one plastic surgery expert, who has expressed his theories to explain her change, as well as from fans who think her original natural look was better.
Let’s take a look at her transformation over time, featuring photos from now back to the beginning, as we explore her evolution from a lawyer and model to a prominent political figure.
From San Francisco Roots to Legal Star
Guilfoyle, 56, was raised in San Francisco, California. Guilfoyle’s mother, Mercedes Marie Guilfoyle, was a teacher who helped children with special needs and had roots in Puerto Rico. Her father, Anthony Christopher “Tony” Guilfoyle, was from Ireland and worked in real estate investing.
Tragedy struck early in Guilfoyle’s life when her mother died of leukemia. She was just 10 years old, which left her father to raise her and her younger brother alone.
Despite these challenges, Guilfoyle worked her way through college and law school. Few people know that she had a brief stunt as a model to help pay for her education.
“I knew I wanted to go to law school and it ended up being a great way to pay for it,” Guilfoyle once told People. “I modeled everything from clothes, swimwear, and lingerie, including Victoria’s Secret! I met an incredible number of interesting people through modeling and really learned a lot about self-confidence and self-worth.”
Guilfoyle started working as a lawyer for the city of San Francisco after she finished studying at the University of California, Davis, and the University of San Francisco Law School.
Her profile rose significantly in 2001 when she successfully prosecuted two defendants whose dogs had hurt a woman. This high-profile case brought her national attention and helped launch her into the public eye.
Her professional success coincided with her marriage to Gavin Newsom, a city supervisor from a prominent family who was later elected mayor of San Francisco in 2003. He is the current Governor of California.
While living in San Francisco, Guilfoyle actively participated in local life. She supported many charities and developed ties with the Getty family.
Her career trajectory took a dramatic turn in 2004 when she moved to New York to become a legal consultant for MSNBC, CNN, and CourtTV. By January 2006, she had joined Fox News Channel as the host of “The Lineup.”
As Guilfoyle’s professional life flourished, her personal life continued to evolve, keeping her in the spotlight for reasons beyond her career achievements.
From Newsom to Trump Jr.
After her divorce from Newsom in 2006, Guilfoyle found love again with furniture executive Eric Villency. The couple married on May 28, 2006, at Sandy Lane, a resort in St. James, Barbados, with the Rev. Ricky Kirton officiating.
Villency’s family had a well-known furniture company. He led Maurice Villency, the stores his grandfather started. Additionally, he hosted a TV show about design called “Idesign” and graduated from the University of Wisconsin.
The couple welcomed their son, Ronan Anthony Villency, on October 4, 2006. Unfortunately, despite their initial happiness, the marriage was short-lived, and they separated in 2009.
Guilfoyle shared a loving message on Instagram to mark her son’s 17th birthday on October 4, 2023. She wrote that he was the best gift she had ever received and expressed immense pride in the kind and successful young man he had become.
Years after her divorce from Villency, Guilfoyle began dating Donald Trump Jr. in 2018, following his separation from his wife, Vanessa. The couple’s relationship quickly became serious, and they got engaged in 2020.
In a 2022 Valentine’s Day Instagram post, Guilfoyle openly shared her affection for her fiancé. She described him as her closest friend, a source of strength, and her lifelong partner, expressing excitement for their future together.
From Fox News Host to Political Figure
Guilfoyle’s connection to the Trump family elevated her political profile significantly. She played a key role in Donald Trump’s campaigns, becoming known for her fierce loyalty and passionate speeches.
At the 2020 Republican National Convention, she delivered a memorable address, famously declaring, “The best is yet to come!” She also spoke at Trump’s rally before the January 6th attack on the Capitol, where she said, “Look at all of us out here—God-loving, freedom-loving, liberty-loving patriots that will not let them steal this election!”
Her dedication to the Trump cause was rewarded in December 2024 when President-elect Trump announced her nomination as the U.S. ambassador to Greece.
After the announcement, Guilfoyle expressed her gratitude, “I love President Trump. He has been my great friend for over 20 years.”
The appointment followed Trump’s pattern of placing close allies and family members in key roles, similar to his previous appointment of the father-in-law of his daughter Tiffany, Michael Boulos, as a senior adviser to the Middle East, and the father-in-law of his daughter Ivanka, Charles Kushner, as ambassador to France during his first term.
However, her relationship with Trump Jr. changed around the time of this announcement when he was spotted holding hands with Palm Beach socialite Bettina Anderson.
According to sources who spoke with People, Trump Jr. had been dating Anderson for about six months and had even taken her “on a trip to Alaska and introduced her around as his girlfriend when he was still very much with Kim.” Allegedly, Guilfoyle largely ignored the situation because she enjoyed the influence and affluence dating the president’s son brought.
Shortly after these rumors surfaced, Trump Jr. publicly supported Guilfoyle’s nomination, writing on X, “I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”
I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First. pic.twitter.com/S3FjxqCgCx
— Donald Trump Jr. (@DonaldJTrumpJr) December 10, 2024
One insider explained that the engagement had lasted a long time and seemed to be in a state of limbo. Despite the split, the Trump family reportedly continued to hold her in high regard.
The source emphasized her intelligence, loyalty, and strong ties to the family, noting that she had been close to them even before her relationship with Trump Jr. In fact, she had known the current president personally before ever meeting his son.
Now, let’s take a look at her appearance years ago, and the striking difference.
From Natural Looks to New Face
As Guilfoyle’s career evolved from law to media to politics, so too did her appearance. Her transformation has been the subject of much speculation.
Plastic surgeon Dr. Gary Motykie shared his professional opinion on Instagram, suggesting that Guilfoyle had likely “dabbled” in fillers because her cheeks seemed much fuller than in previous public appearances.
“She’s lost a lot of weight recently,” he said on a reel, “and that can take an effect on the face, particularly when we get a little bit older. As we’re aging, we’re actually losing naturally fat volume on our face.”
The doctor went on to explain that if people are dieting or using Ozempic, the effects will be even more noticeable. However, the results can also make people look “tired.” Many will resort to common beauty procedures, like fillers and fat-grafting.
Also because of her age, Dr. Motykie believes she may have also had face and neck lifting. While Guilfoyle has not publicly commented on whether she has had any cosmetic procedures, the difference between her earlier photos and more recent appearances has been striking enough to prompt widespread discussion among fans and followers.
When she posted photos celebrating her birthday on March 10, 2025, comments flooded in with opinions about her look. Some followers expressed concern about what they perceived as cosmetic enhancements. One commenter wrote directly, “Please cut back on the lip fillers.”
Another offered more detailed advice, “Kim the lip filler and dark eyelashes needs to go!! It isn’t attractive on you. Embrace your natural beauty. You and your friends need to quit making your face and body be something it isn’t meant to be [sic]!!!” A third simply stated, “Ladies Get Rid Of The Big Lips and Eyebrows [sic]!!”
Yet many admirers continue to praise Guilfoyle’s appearance. “Beautiful lady ❤️🔥😍🔥,” wrote one supporter on her birthday post. Another commented, “Always looking amazing, Kimberly 😮 Happy birthday 🥂.”
Interestingly, when Guilfoyle shared throwback photos from earlier in her career, followers often expressed nostalgia for her former look.
One netizen wrote, “Your natural beauty.” Another added, “Pure Beauty! Absolutely Gorgeous. :)” Others simply respond with amazement, with one fan writing, “WOW 😲.”
From her early days as a San Francisco prosecutor to her current role as a political figure and diplomat, Guilfoyle’s transformation reflects not just changing personal and professional aspirations, but also a desire to keep her youthful looks, similar to this star who is beloved by everyone in Hollywood.
