The Complete Transformation Of Kimberly Guilfoyle

Chances are that — unless you've been following the political scene of the United States super closely, watching Fox News religiously for years, or having an obsession with the Trump family — you probably haven't heard of Kimberly Guilfoyle. If you have, it's still possible that you don't really know too much about her. But globally famous or not, Guilfoyle has undeniable fashion prowess and contagious confidence that definitely makes her worth paying attention to.

As Guilfoyle is engaged to Donald Trump Jr., the son of the president-elect, and has served various roles for the Republican Party throughout her career, she's a controversial person to some and a highly beloved one to others. But we can all agree on this: Everyone can learn a thing or two about bold fashion and female resilience from her journey, which has been marked by a lot of figure-hugging black dresses. So here it is — the very interesting transformation that Kimberly Guilfoyle underwent over the years!

Kimberly Guilfoyle — who got her law degree from the University of San Francisco Law School in the '90s — was slowly making a name for herself in the early aughts. Guilfoyle had quite an impressive career as a prosecutor, admitting in 2001 that working was a priority for her. "It's not just who's dating who, parties and silliness," she told SFGate, clearly taking on life with an optimism that may seem either refreshing or naive. "If you put your mind to it, anything is possible."

However, thanks to her slender physique and beautiful facial features, Guilfoyle was also making her way into modeling, and in 2005, she even walked in San Francisco Fashion Week. Guilfoyle later admitted that modeling wasn't really a major passion of hers but rather a "means to an end, period." Guilfoyle's career-driven enthusiasm didn't come out of nowhere. The television news personality admitted that it was the passing of her mother when she was only 10 that became a turning point in how she views her future. "My most defining moment was the death of my mother," she told SFGate.

In 2001, Guilfoyle and politician Gavin Newsom got married, and two years later, he was elected as mayor of San Francisco. The two quickly gained popularity as a couple and were even proclaimed as "the new Kennedys" by local outlets. Unfortunately, the picture-perfect appearance they were delivering wasn't real — and in January 2005, the two announced their separation. Later on, it was revealed that Newsom was having an affair, but it is unclear whether Guilfoyle knew of it at the time.

Kimberly Guilfoyle had big plans for her future when she moved to New York City in 2004. Initially, she worked as a legal consultant for news-based channels like CNN, but it seemed as if she wanted more of a spotlight, and the Fox News Channel offered her that. In 2006, Guilfoyle became a host on the channel's show "The Lineup."

Being on television surely allowed Guilfoyle to explore and have even more fun with fashion. Attending fashion events was a must for her, and often, she would also find herself on the runway. "I was able to meet a tremendous [number] of interesting people through modeling, and I really learned a lot about self-confidence and self-esteem," Guilfoyle revealed to Cosmopolitan a few years later. "I learned how to cue into my own autonomy as a woman." Her personal life was thriving just as much. In 2006, she tied the knot with businessman Eric Villency, and only a couple of months later, the two welcomed their son Ronan.

While Kimberly Guilfoyle's career as a television news personality was consistently growing, her personal life was seemingly suffering. In late 2009, Guilfoyle and her second husband Eric Villency got divorced — and the Fox News star seemingly had enough of love, at least for the time being.

Instead, she shifted her focus even more to fashion, which became an incredibly important part of her life. Guilfoyle regularly attended New York Fashion Week shows, always ensuring she was dressed to the nines. At the time, her go-to signature look was a posh and preppy minidress, à la Blair Waldorf in "Gossip Girl." One thing we couldn't help but notice is that the former prosecutor was gravitating toward black-and-white combinations, avoiding bold and bright colors. A deep side part and full-glam makeup always accompanied her look, making her instantly recognizable everywhere she went.

In 2011 and 2012, Kimberly Guilfoyle's private life remained very much private — as little was known about any romantic relationships she may have had. Seemingly, the star focused on work and raising her son Ronan. In 2012, she gushed to Glamour about her work environment. "'The Five' is so special because we all have such diverse backgrounds," she said. "It's such a nice mix of men, of women, and the variety of where we come from, different walks of life, different occupations, and certainly different viewpoints. That's what makes it so unique."

Fashion-wise, she was thriving, and with even more invitations to industry events, the television news personality was allowing herself to have some more fun with her style. Never branching out from her comfort zone too much, Guilfoyle began embracing some color while still ensuring she never went too bright or into the realms of neon. One of our favorite Kimberly Guilfoyle looks from this era is the long-sleeved teal minidress that she wore in 2011 to the "The Ides of March" premiere in New York City.

After a brief exploration of colorful fashion, Kimberly Guilfoyle realized that she adored the classic vibe black dresses come with. And just like that, black became her go-to choice for red carpets. While we've seen the star rock numerous minidresses, it was her gown moments that left us in awe — in particular, the stunning black-lace maxi dress that she wore to the New Yorkers for Children Dinner in 2013. It was chic and elegant, yet still sexy and modern thanks to the see-through lace parts.

In 2014, during Guilfoyle's candid conversation with Cosmopolitan, she revealed her best advice for young people who are chasing a career. "The one message I always send to young people is: Don't be afraid to try different things to see what feels right and what's a good fit," Guilfoyle shared. "Then once you're in, if an opportunity presents itself, don't be afraid to go through that door and explore and see if it's something you could become excited about or that you go to bed at night and wake up in the morning and feel good about. If you do, then you know you're on the right track."

2015 marked an important year in Kimberly Guilfoyle's career as she released her non-fiction book "Making the Case: How to Be Your Own Best Advocate." As of writing, the book has a 4.2 star rating on Goodreads. At the time of its release, it mostly received positive reviews, with Forbes even calling it "sound advice from someone as qualified as they come."

Apart from broadening her professional experience, Guilfoyle continued showcasing her love for sleek black clothes as she kept on attending fashion events. While she stuck to black for her fashion-industry moments, when she was hosting "The Five," she often went for eye-catching dresses in bright colors like red and blue.

In 2016, Kimberly Guilfoyle was first linked to the Trump administration, which she confirmed in 2017 by revealing that she was being considered for the position of the White House press secretary. "I'm a patriot, and it would be an honor to serve the country," Guilfoyle shared at the time (via AOL). "I think it'd be a fascinating job, it's a challenging job, and you need someone really determined and focused, a great communicator in there with deep knowledge to be able to handle that position." Ultimately, Guilfoyle wasn't selected for the position. 2017 marked her departure from Fox News, reportedly due to accusations of sexual harassment.

During the second half of the 2010s, the former prosecutor's fashion was as flawless as ever. Still leaning toward black fashion, Guilfoyle began incorporating some patterns into her style, often gravitating toward black-and-white dresses. For Us Weekly, the television news personality opened up the doors to her closet. "Every girl knows you can never have enough closet space. And in New York City, wow it's like you need a magic wand to figure it out," she said. "I tried to make sure to maximize every inch of space." When asked how many pairs of shoes she had, Guilfoyle responded, "The truth would frighten me. There have been estimates of about 500 pairs," she revealed.

In 2018, Kimberly Guilfoyle found herself in the spotlight thanks to her relationship with Donald Trump Jr. For those who aren't familiar, Trump Jr's ex-wife Vanessa (who underwent a stunning transformation of her own) filed for divorce in the spring of 2018, and by mid-summer, Guilfoyle's relationship with Donald Trump's oldest son became public.

Guilfoyle — who is nine years older than Trump Jr. — seemed very happy during one of the couple's first outings together. The two were together at the White House on the Fourth of July, 2018, and a source revealed to Us Weekly that they looked very much in love while on a date that June. "Donald stood and kissed her on the lips when she arrived and they hugged each other," the insider revealed, adding, "They were laughing all throughout lunch and Donald and Kimberly took photos with two people who asked."

With the new relationship, it certainly seemed as if Guilfoyle regained some confidence as her fashion choices became bolder than ever. The television news personality was never one to shy away from showing some skin, but now, plunging necklines and basic crop tops had become a closet staple for the star. 

Kimberly Guilfoyle continued exuding confidence, and in 2019, she was known as one of the women in Donald Trump's family whose fashion is fierce and flawless. However, even those who have great style can make a mistake, and that is exactly what happened to Guilfoyle at the 2019 New York Fashion Week. The former prosecutor attended the Zang Toi show in a little black dress that looked cute and classy — but flash photography wasn't its friend. And just like that, Guilfoyle ended up showing a bit more than she intended to. Of course, a fashion faux pas happens to pretty much everyone in the spotlight at some point, but we're hoping this served as a fashion lesson to Guilfoyle.

Apart from rocking bold looks (both good and bad) and supporting her designer friends' fashion shows — Guilfoyle was also serving us selfies on Instagram, where we noticed that her go-to posts in 2019 were duck-face pics. Hey, we've all done them, so there's no judging, but we're glad that this Guilfoyle era is over.

In 2020, the world went into a temporary standstill due to the coronavirus pandemic, and for Kimberly Guilfoyle, this meant enjoying some more free time with Donald Trump Jr. Together, the two explored nature, something she frequently shared on Instagram.

In 2021, Guilfoyle and Trump Jr. got engaged, although news of their engagement wasn't made public until 2022. According to Daily Mail, Trump Jr. proposed to the television news personality with an eight-carat diamond ring on New Year's Eve 2020 — which also happens to be his birthday. "They've been together for almost four years now and have been friends for 15 years," an insider revealed to the outlet. "They've kept it private for the past year as they settled into life in Florida after moving from New York. Both are focused on their children — they have six between them — and their work."

One thing we couldn't help but notice is the change in her makeup routine. Even though Guilfoyle always preferred a dramatic look, she was now all about messy smokey eyes and false lashes. This certainly makes us wonder whether she and Melania Trump share the same makeup artist. Then again, we wouldn't really recommend that Guilfoyle have Melania Trump as a makeup role model, as the first lady is known for more than a few makeup mistakes.  

By 2022, it was clear that Kimberly Guilfoyle had become one of the most prominent Trump women (though not one of the Trump women who loves going makeup-free), and her support was always visible. Whether she was attending Ivana Trump's funeral or speaking at political conferences — Guilfoyle became a very important voice for Donald Trump.

The former prosecutor's relationship with her fiancé Donald Trump Jr. was flourishing, and Guilfoyle gushed about their partnership in an interview with Metropolitan. "Don and I knew each other for years but, when we went on one date years later that was it. Sparks. In fact, we have been together from that night on, happily ever after," she said in December 2022. "Don and I are a perfect match ... We share the same inner passion and fighting spirit. What people may not know is that I am very traditional, which I learned from my parents." With her more prominent involvement with Donald Trump's family, a change in Guilfoyle's style was noticeable. Now, she was dressing more conservatively as the days of a bare midriff and deep-V necks seemed to be gone.

In 2024, Kimberly Guilfoyle played a big role in popularizing Donald Trump in the presidential election — which the former president ended up winning. While her career in politics is undoubtedly continuing to thrive, Guilfoyle celebrated a more important milestone this year — her son turning 18. "Happy 18th Birthday, Ronan! Watching you grow into the incredible young man you are today has been my greatest joy. Love you to the moon and back," Guilfoyle wrote on her Instagram. In 2024, we also got to see more of a new side to Guilfoyle as she shared quite a few cooking videos on her social media, showcasing her favorite recipes.

While she has lived multiple lives over the years — from being a model to a prosecutor to a television host to now being the fiancé of the president's son — there is no denying that Guilfoyle has undergone an impressive transformation, proving that one can reinvent themselves and change their career path at any age. Love her or hate her, there's also no denying that she is the most fashionable thing that ever happened to the Republican Party, and for that, we applaud her!