Kimberly Guilfoyle's Hair Transformation Drastically Changed Her Appearance

Kimberly Guilfoyle is one set of "I dos" away from joining the Trump family dynasty, but the news that often follows the former Fox News host centers on her personal style. Guilfoyle has garnered plenty of attention with her bold, expressive wardrobe, making her a standout at the endless conventions and political rallies at which she thrives. But despite her obvious love for getting dressed up, many of Guilfoyle's outfits, especially while campaigning for Donald Trump, have been total failures according to fashion enthusiasts and even those with a mild sense of style. Unfortunately, her evolving appearance has also inspired debate about whether she has a history of extensive plastic surgery use.

While it's totally possible that the career Republican may or may not have penciled in a few cosmetic appointments into her packed schedule over the years, it's her chameleonic hair transformation that's seemingly altered her looks the most during the time she's spent as a public figure. While she currently favors heavy, highlighted layers, over the last two decades or so, Guilfoyle has tried out a number of hairdos, ranging from short to long, light to dark, making several stops in between. Don't believe us? Here are some of Guilfoyle's most notable hair transformations throughout her career.

Kimberly Guilfoyle wasn't always a conservative host and Trump supporter. Nor was she always in a relationship with Donald Trump Jr. In the early 2000s, Guilfoyle was a high-profile prosecutor whose marriage to Gavin Newsom was in full swing. The up-and-coming conservative was also in proximity to some pretty left-leaning ideology at the time. But it's not her shifting political affiliations or even the 20-year age difference that had her looking totally and completely unrecognizable. That credit goes mostly to her hair. While she currently seems to enjoy super long hair, seemingly padded with ungodly amounts of extensions, Guilfoyle once sported a much more natural look.

In 2004, Guilfoyle looked fresh-faced and youthful as she rocked a simple, shoulder-length cut in a natural shade of brown. Aside from a side part and a few face-framing layers, there was nothing particularly memorable about this haircut, which totally would've helped her to blend in perfectly with the cast of "The Real Housewives of San Francisco." You know, if Bravo had ever managed to get the failed franchise off the ground. "We cast here once. We clearly didn't cast the right people," Bravo bigwig Andy Cohen once admitted (via SF Gate). Ahh, the missed possibilities. Anyhow, at least there's proof that Guilfoyle can throw a great look together when she feels compelled. Bonus points for the purple dress!

In January 2005, Kimberly Guilfoyle took a break from hitting the pavement to attend the premiere of "The Exonerated," produced by her then-employer, Court TV. The movie premiere was held in New York City, and the California native totally embraced the chic, high-class ambiance of the ritzy city. The star of Guilfoyle's look was a slightly grown-out version of her housewives' haircut. While she kept her brown base and subtle highlights, she'd grown out the cascading layers she'd rocked the year prior, adding some much needed weight to her blunt cut. Guilfoyle also embraced sleeker tresses turned slightly under, probably with a curling iron or even a round brush.

Guilfoyle dressed in a classy, reserved, all-black number. She paired a knit black turtleneck with a frilly, ribbed cardigan, which gathered at the waist. And while Guilfoyle's designer of choice this night is unknown, the look definitely seems like it was curated with an expert's touch. Bonus points for her pulling this look together mere weeks after her impending divorce from Gavin Newsom was made public. "Over the past 10 years, we have developed a tremendous bond of love and respect for each other," read the exes' divorce statement, according to SF Gate. "Unfortunately, the demands of our respective careers have made it too difficult for us to continue as a married couple," they added. 

In April 2013, Kimberly Guilfoyle, who'd only divorced her son's father, Eric Villency, a few years earlier, embraced her philanthropic side by showing up to New Year's in April: A Fool's Fete, a charitable event put on by the New Yorker's For Children. Interestingly, it seems this was the event that kicked off her love for larger-than-life hair. But unlike some of the other unflattering 'dos she's rocked in recent years, her beauty pageant-esque hair, which was probably held in place with hairspray, perfectly matched the event's black tie theme. It's also important to note that it seems that Guilfoyle was slowly warming up to embracing longer lengths and more defined waves. But this was just the start.

To go with the hair, Guilfoyle threw on a black, strapless, off-the-shoulder dress covered in black, translucent, meshed sleeves. It was overlaid with a swirling beaded design, which extended over the entirety of the dress's length. Guilfoyle also played around with a much bolder, smoldering night look, including bright pink lipstick and a thick-lined cat eye. Although this dress and overall look were still miles ahead of some of her more recent fashion choices, the execution wasn't nearly as refined as some of her looks that defined the early aughts. And while there's nothing wrong with experimentation and trying on a new persona, this was perhaps the start of her fall from fashion grace. 

By 2019, Kimberly Guilfoyle was in the middle of a major style transformation that left little room for subtlety. In fact, it seems she was living by the motto, "The bigger the better." However, she still had a little room to play around before totally losing the plot. In this photo, Guilfoyle flaunted a slightly different, more dramatic version of her pageant hair, although with much longer layers and a middle part. It also appears that someone introduced the Republican to thinning shears because her hair didn't seem nearly as heavy. That, paired with the extra-long layers, added a little extra balance to the bold style. It also appears that Guilfoyle embraced not only highlights but warmer tresses overall.

Instead of opting for her signature brown, the base of her hair leaned more copper or even mahogany brown, making the overall look appear less harsh. Plus, the added highlights, which were much lighter than what she usually went for, added even more depth to her hair. Finally, Guilfoyle styled her hair in bold curls, which, when brushed out, gave the style a nice, uniform texture. Interestingly, Guilfoyle's red wrap dress actually elevated this particular look in ways her clothes don't always achieve. If only she took her former style cues more often, people would have much, much less to say about her personal style and more about her views. Actually, you know what — scratch that.

There's no denying that Kimberly Guilfoyle's recent style choices exist on a totally different plane than her frocks from decades past. And while there's nothing wrong with evolving or embracing high fashion during each stage of life, Guilfoyle has cultivated a reputation for being overly flashy, extravagant, and overall distracting, even when the venue doesn't call for it. Enter the hairstyle Guilfoyle wore in an Instagram post from March 2024. Donald Trump's future daughter-in-law wore super long, bulky hair extensions that reached the middle of her waist. She styled the hair in long waves, accented by thick, distracting curtain bangs that weighed down her look and did a major disservice to her white mini-dress.

That said, all was not lost. While Guilfoyle's hair wasn't all that impressive, she managed to take a break from supporting Trump to get all dolled and lend her time to an amazing cause: a dog rescue organization. "Wine, Women, and Shoes brought the house down for @BigDogRanchRescue!," she posted to Instagram. "It was an unforgettable weekend of style, compassion, and four-legged fun. The two-day event raised critical funds to support medical needs at @BigDogRanchRescue and help save more dogs." She continued, "Thanks to everyone who joined us in supporting our furry friends!"