Kimberly Guilfoyle's Complete Style Transformation

Kimberly Guilfoyle's fashion choices are just like her politics — Americans either love them or they hate them. A casual glance at the Republican newscaster's Instagram reveals posts overflowing with compliments. "Lookin' good Kimberly! God bless," wrote one fan below a photo of her speaking at the Texas Youth Summit in September 2024. Another left a comment lauding what they saw as the gracefulness of her style. "Elegance," they wrote.

Despite these adoring words, Guilfoyle has received quite a bit of criticism for her sense of style. Vanessa Friedman of The New York Times hinted that the newscaster's wardrobe could be anti-feminist — and even used her 2024 RNC outfit of "a scarlet dress and spike heels" to illustrate the concept of "the Palm Beach billionaire take on the trad wife." Joanna Coles from The Daily Beast took things even further when she critiqued Kimberly Guilfoyle's shocking transformation from a casually dressed Bay Area lawyer to "a Republican adviser with ... heavy dark eye makeup that would make even Cleopatra say, 'Honey, hold the kohl.'"

Obviously, adoring or detesting Guilfoyle's style is ultimately a question of personal preference. That being said, it's true that Guilfoyle used to embrace a lighter, more natural look. Back when she was a Democrat, the newscaster wore more casual and corporate clothes. As her politics have shifted, however, Guilfoyle has come to embrace an increasingly Barbie-esque sense of fashion.

These days, Kimberly Guilfoyle is known for wearing outrageously colorful outfits, decorated with glitter and sparkles galore. However, the former Fox News host was not always such a fashionista. As a child growing up in the San Francisco Bay Area, Guilfoyle did not focus much on developing her personal style. Her parents, Anthony Guilfoyle and Mercedes Gerena, apparently dressed her in simple yet comfortable children's attire — without any of the Barbie flair that we see her sporting now. If anything, she grew up in an environment where simplicity and comfort triumphed over all else.

In an interview with SFGate, Anthony Guilfoyle said that he wanted to raise his daughter not to focus too much on material things. He would apparently tell her, "The world is about people, not possessions or silly trinkets. When the lights go out, the question is what it always has been: What did you do for others when you had a chance?"

Back in 2003, Kimberly Guilfoyle was not a Republican. In fact, she was a very involved Democrat who enjoyed attending blue fundraising events. At one such 1994 gathering, she crossed paths with Gavin Newsom — now the left-leaning governor of California. Back in the day, Guilfoyle found Newsom attractive and entertaining. They became friends and eventually started dating. By 2001, they were married, and two years later, Newsom began running for mayor of San Francisco.

For Guilfoyle, Newsom's political aspirations represented a major life change. Before she had to campaign alongside her husband, Guilfoyle was a well-known San Francisco prosecutor and gravitated toward a more professional style. As she found herself thrust into the spotlight, though, Guilfoyle discovered that her fashion choices were more important than ever. Likely in hopes of appealing to voters, the future first lady of the city kept her clothes clean-cut yet casual. 

In one 2003 photo of Guilfoyle campaigning alongside former President Bill Clinton, she is featured wearing a professional, collared garnet-red jacket. Somewhat reminiscent of a work suit, the jacket contained subtle shoulder padding. However, as the piece is meant to come across as casual, Guilfoyle left the first two buttons undone. To make her outfit even more relaxed, she added an inexpensive chunky necklace. All in all, this style choice comes across as professional without bordering on corporate — and casual without appearing unkept. 

In 2003, Gavin Newsom won the mayor's seat — meaning that Kimberly Guilfoyle became the first lady of San Francisco. Although Guilfoyle had once worn suits for her job as a prosecutor, her new role in local politics called for a more formal sense of style. Indeed, San Francisco's first lady was expected to cut ribbons and attend award ceremonies. At these more formal events, Guilfoyle embraced more evening wear.

This was evident in 2004 at the 15th annual GLAAD Media Awards. At the event — which sought to recognize those in the media who represented LGBTQ+ characters in an unbiased way — Guilfoyle wore a fashionable black spaghetti-strap dress. She kept her look professional, however, by pairing the cocktail wear with a set of black glasses that gave her a very "nerdy chic" vibe. Overall, Guilfoyle's style did a fantastic job of marrying the formality of the event with the seriousness of her own identity as a career woman.

Jackie Kennedy remains one of the biggest fashion icons of all times, giving popularity to dozens of trends and designers. One of the many political partners to emulate her style was Kimberly Guilfoyle — who leaned heavily into a Kennedy look during her time as the first lady of San Francisco. This was especially apparent in 2005 when the future King Charles III and Camilla, Queen Consort, traveled to Northern California. In an effort to show the British royals around, Guilfoyle accompanied them to the comedic "Beach Blanket Babylon" show. As she could not wear just any outfit to the event, Guilfoyle opted for a white coat dress with a black bow at the neckline.

Here, Guilfoyle's style was deeply reminiscent of Kennedy's. With a high neckline and semi-professional cut, this black and white dress resembled many of the suits that Kennedy would wear on her own official outings in the '60s. It particularly called to mind the iconic pink suit that she wore when her husband was assassinated. With a wide, dark collar and a loose, trapezoid shape, Guilfoyle's attire contained many of the same style elements that we can see in Kennedy's most unforgettable outfit.

Interestingly, around the same time as Charles and Camilla's visit, the press was lauding Gavin Newsom as a potential future "Kennedy." Harper's Bazaar touted his "Kennedy-esque mop" of hair and celebrated his marriage to Guilfoyle as "one of the most glamorous political unions since Jack and Jackie."

Although Kimberly Guilfoyle did her best to dress as the first lady of San Francisco, her efforts were short-lived. At the beginning of 2006, Guilfoyle and Gavin Newsom got a divorce. By May, Guilfoyle found herself walking down the aisle again — this time alongside Eric Villency. Although Kimberly Guilfoyle and Eric Villency's relationship may have seemed a bit rushed, there was something binding the pair together. At the time of their wedding, the couple was already expecting their son, Ronan Villency, who would be born that October.

During the initial months of Guilfoyle's new marriage, she found herself exploring maternity styles. While many women of her generation went for tighter-fitting pregnancy wear — all the better to show off one's bump — Guilfoyle was more attracted to flowing looks. This was obvious when the paparazzi captured a few shots of her walking around with Villency hand in hand. Sporting a loose white dress and a casual pair of flip flops, Guilfoyle emulated a Greek goddess. Her outfit showed off her bump without restricting her movement, making it very practical for what appeared to be a warm summer day.

Around the same time that she married Eric Villency, Kimberly Guilfoyle was approached with a fascinating professional opportunity. Fox was looking for a host for its legal talk show "The Lineup," and Guilfoyle was at the top of their list. As a former prosecutor who had also had modeling experience, Guilfoyle knew that her skill set combined technical knowledge with camera readiness. She jumped at the chance to host her own show and signed a contract with the media giant.

Although "The Lineup" was ultimately unsuccessful (it was canceled after just five episodes), Guilfoyle remained on good terms with Fox. To put forward her best face to the company, Guilfoyle dressed extremely professionally in the period between 2006 and 2008. The vast majority of her outfits during this time incorporated somber shades, like gray or black. She also wore a lot of blazers — although many of her dresses also had a more corporate feel.

This was evident at the 2007 Louis Vuitton Party of Love. On this occasion, Guilfoyle sported a pale gray dress and a pair of matching pumps. Although the event was supposed to be more of a party than a work function, Guilfoyle's dress included a V-neck collar that was clearly meant to resemble the folds on a traditional suit. Her small studded earrings also kept things simple — giving off the feeling that she was ready for a day in the office.

Although Kimberly Guilfoyle wore a whole lot of gray in her first few years as a media personality, she began to experiment with more colorful pieces in 2010 and 2011. By then, she was a more frequent guest correspondent on Fox shows, like the "Geraldo Rivera Reports" and "The Strategy Room." Perhaps feeling a bit more secure in her career, Guilfoyle seemed open to dressing boldly.

This was especially true at a screening of "The Sorcerer's Apprentice" which was organized by the Cinema Society & Amnesty International in New York. In stark contrast to her typical corporate style, Guilfoyle went full Hollywood for this event. In a hot pink dress and a pair of chandelier earrings, the media personality looked like she had raided Barbie's closet. Unlike the seriousness of her dark suits, this outfit was fun, lighthearted, and colorful.

Interestingly, Guilfoyle would bring another blast of color into her wardrobe just a few months later at the Doggy John gallery exhibition in May 2011. This time, she wore a deep magenta dress and accessorize with a fun part of hoop earrings. Although most of her other outfits from this time remained steeped in darker colors, these two brighter outfits represented a major transition in Guilfoyle's fashion evolution.

By 2012, Kimberly Guilfoyle was a staple at Fox and was no longer afraid to wear brighter, more vibrant colors. If anything, she began to develop a passion for reddish shades, like scarlet, vermilion, and magenta. She showed up to Mercedes-Benz Fashion Week that year in a bright red dress with capped sleeves and a buckled waist. Leaning all the way into the boldness of the look, she contrasted the color of her dress with a black manicure.

Following this event, Guilfoyle began to wear red to more occasions. In 2013, the television personality sported a red floral dress to the "Inside Edition" anniversary party. She also wore a simple scarlet frock to a New York City screening of "Elysium" that same year. 

By 2014, she had begun to experiment with the "Miss America" look she often sports today. She even attended a screening of "Fury" wearing a low cut vermilion dress that showed off her cleavage. This combo of a bright color with a V-neck cut has become a key element of her signature style today.

As Kimberly Guilfoyle leaned increasingly into a more Barbie-esque sense of style, she also increased her make-up use and apparently dipped into a bit of plastic surgery. In 2016, at the Fool's Fete party in New York City, Guilfoyle was photographed making a dramatic half smile as opposed to her more usual toothpaste ad grin. The lack of facial expressions in photos of her from that time make it seem like she might have experimented with botox or fillers. Although the newscaster has not confirmed or denied plastic surgery rumors, it's undeniable that her style began giving stronger "Miss America" vibes.

Her face was not the only thing she changed at this time. Kimberly Guilfoyle also underwent a major hair transformation that involved coloring her locks and growing them out longer. With her dramatic waves and chest-length hair cut, Guilfoyle's style was not quite as "beauty pageant-esque" as it is today. However, she definitely departed from her career-girl look and began to lean into something a little more glam.

By the time Kimberly Guilfoyle started dating Donald Trump Jr. in 2018, she already embraced a more dramatic, Barbie-style look. However, during her relationship with the eldest Trump son, Guilfoyle began to wear even more pronounced eye makeup. If she already enjoyed using eyeliner before, the newscaster took her smoky eye to a whole new level. Photos of Guilfoyle since dating Donald Trump Jr. show her wearing thick black eyeliner on the top and bottom of her lids, as well as dark eyeshadow and what appear to be eyelash extensions.

Although Guilfoyle seems very happy with this look, she has received a lot of backlash for leaning into such a makeup-heavy style. In 2021, she shared a selfie to Facebook — revealing that she had caked on the dark makeup for a weekend in "the outdoors." One of her concerned fans commented, "Who camps with all that makeup? That's not you!" However, at the end of the day, the only person who needs to be happy with Guilfoyle's makeup is Guilfoyle herself.

As things have grown more serious between Donald Trump Jr. and Kimberly Guilfoyle, the latter has found herself spending more and more time in South Florida. There, fashionistas famously experiment with vibrant, over-the-top colors. In this fun, lighthearted fashion environment, Guilfoyle appears to have discovered new ways of expressing herself through clothing.

This was especially clear in 2023 when she took to Instagram with a photo of herself wearing bold purple attire. "Great day with my amazing friend, @cameronpatrickneth, the most talented custom jeweler in Florida," she wrote.

In the shot, jeweler Cameron Patrick Neth was wearing a purple suit with a violet and while polka dotted undershirt. Guilfoyle matched his vibe completely, wearing a lilac dress. Not to be outdone, she paired the frock with a fur overcoat in a softer, pastel purple shade. This totally outrageous outfit contrasts fully with the sort of clothes that Guilfoyle would wear in New York.

As time goes by, Kimberly Guilfoyle has gravitated toward increasingly cleavage-forward clothing. While many of her more "career girl" outfits sported higher necklines and lower hems, Guilfoyle's 2024 wardrobe has been all about the plunge. In her role as a hostess for the Abraham Hamadeh fundraiser at Mar-A-Lago, Guilfoyle wore an extremely low-cut V-neck dress that went almost down to her bellybutton. Chain links provided some coverage of her chest, but the outfit definitely centered her cleavage. 

Fascinatingly, Guilfoyle has leaned so heavily into this sort of low-cut look that she even sometimes wears deep-dipping dresses at home. One video of the newscaster — which she shared on Instagram — shows her cooking a chicken dinner in a teal dress with a plunging neckline. In the caption of the video, Guilfoyle admitted that she had prepared this particular meal right after filming a new project. Even so, the fact that she didn't kick off her white stilettos before seasoning her chicken shows that Guilfoyle is totally dedicated to her new look. Although her 2024 style differs greatly from the outfits she wore in 2004, Guilfoyle seems confident in her clothes — and that's all that matters.