The Most Inappropriate Outfits Kimberly Guilfoyle Has Ever Worn

Kimberly Guilfoyle certainly knows that in the game of politics, fashion is a mighty tool in building reputations. Think Hillary Clinton's bold, colorful pantsuits. Or Donald Trump's trademark red tie. The association of these wardrobes to their respective politicians is so strong that conjuring up mental images of them in anything else would be near impossible. While Guilfoyle may not share Clinton or Trump's stature, she is a speaker in the modern political scenario, and she knows how to make an impact with her outfits. Be it an election rally or a local street fair, the former attorney is always dressed to the nines. It's undoubtedly a conscious choice. As celebrity stylist Lauren Rothman told the Financial Times, "Optics are a non-negotiable, important star power for politicians. This is intentional." 

Guilfoyle's commitment to dressing up is not a recent occurrence, though. Fitted dresses and skirts have been a part of her public persona since her glory days as a Fox News host. By making herself a noticeable enough public personality, Donald Trump Jr.'s girlfriend has racked up enough credit in the domain of political fashion. Despite being a seasoned fashionista, Guilfoyle has still had her fair share of fashion misfires. 

What's a wedding without some drama? It was a joyous occasion for the former first family as Tiffany Trump tied the knot with her businessman fiance Michael Boulos at Mar-a-Lago in 2022. Many of the Trump women showed up in their wedding best, coordinating in pastel shades and lighter hues for the day ceremony. Kimberly Guilfoyle attended, too, contrasting the theme of the bridal party in an all-black dress with statement sleeves. 

Now, anyone who has ever indulged in wedding pictures at their own or another's nuptials knows that uploading them to the 'gram — in all their aesthetic propriety — is serious business. It was touted as one of the reasons why Ivanka Trump seemed to have cropped Kimberly Guilfoyle out of the family picture she shared on Instagram. The viral snap featured the who's who of the Trump crew, including former First Lady Melania Trump and the bride's mother, Marla Maples. 

This supposed snub was first caught by hawk-eyed social media users, who then had a field day trying to decode it. The drama this stirred even landed Guilfoyle's picture on "The View," where the panel tore into her choice of outfit — a reaction that was, in turn, criticized by some viewers. Not long after the controversial photo ignited the internet, Ivanka seemingly tried to douse the fire by uploading an Instagram Story of the original, uncropped photo that showed Guilfoyle standing beside her. 

The 2020 Republican National Convention (RNC) was a star-making moment for Kimberly Guilfoyle. It elevated her from her widely known status as Donald Trump Jr.'s girlfriend to one of the foremost characters in the newer chapters of Trumpism. "Fiery," "loud," and "forceful" were just some of the words used to describe Guilfoyle's high-decibel speech on the opening day of the RNC. But those attributes could just as well be used to articulate the impression her event ensemble made on the public consciousness. Clad in a flaming red figure-hugging dress that featured a signature low neckline, Guilfoyle made an impact. It led to The New York Times dubbing her the RNC's "woman in red." 

While red may have seemed like the obvious choice for a personality associated with the upper echelons of the Republican Party that has long capitalized on the color, Guilfoyle's outfit wasn't necessarily well received. Popular stylist Lisa Kline, who has experience working with Republican leaders, told the Financial Times, "I felt her dress was distracting from the moment she walked out. It felt a bit inappropriate. The outfit should not be the headline the next day." And if Kline's dictum about not having to "scream your outfit" is anything to go by, one can conclude that Guilfoyle's RNC dress was a red-hot miss. 

No matter the occasion, Kimberly Guilfoyle isn't one to dress down. The honorary Trump family member was in her dazzling best even for a carnival outing at the luxurious Admirals Cove Club in Jupiter, Florida back in December 2023. In her sparkly Balmain dress and Louboutin heels, Guilfoyle stood apart from Donald Trump Jr. and his children, who also accompanied her to the holiday fair. She took to Instagram to share pictures from the carnival, effusing about the incredible evening the family had. 

While Don Jr. and the kids donned casual tees, sweatshirts, and comfy sneakers, Guilfoyle went with a figure-hugging dress and high heels — hardly a carnival fit. Posing in front of the merry-go-round carousel, as one of her pictures showed, is probably as far as she would have got to enjoying a ride in that attire.

It was not especially surprising, though, given that this is more or less Guilfoyle's default wardrobe. And anyway, someone who owns a bottomless reserve of heels — "about 500 pairs," Guilfoyle once told Us Weekly — would probably use every opportunity they got to flaunt a pair. 

Kimberly Guilfoyle is no stranger to the glam world. Formerly a model herself, she was in the past associated with big brands like Victoria's Secret — a detail that gained mainstream attention back in 2012 when anchor Brian Kilmeade joked about Fox News picking out female hosts from the lingerie brand's catalog (via The Cut). 

A host on Fox's "The Five" at the time, Guilfoyle had defended her modeling career as a means to get through law school. "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," she told Cosmopolitan. It must have been a full circle moment for Guilfoyle, then, to be rubbing shoulders with fashion bigwigs at the New York Fashion Week in 2019. 

She sat front row at Malaysian designer Zang Toi's runway showcase wearing a dress with a pair of butterflies sewn onto the sleeve. Unfortunately, the insect appliques weren't the most memorable detail about Guilfoyle's outfit that evening. Turns out, her dress was a bit too sheer for the paparazzi's flashing lights, which captured stark outlines of her underwear in pictures. 

Who doesn't love pink? But also, who isn't aware of the social baggage it comes with? Given its enduring association with gender — more often than not, to stereotypical extents — pink sticks out as one of the most contentious colors on the spectrum. True, pink has been reclaimed from its prejudiced notions in many ways. But its usage in a political context only adds another layer to its already loaded gender classifications. It's why Kimberly Guilfoyle's Barbie-coded outfit during Donald Trump's presidential campaign in 2020 carried complex connotations. 

For a Women For Trump event in Pennsylvania, the former president's advisor donned an all-pink sheath dress that matched the signage of the rally slogan. Besides being cliché, Guilfoyle's dress also proved to be a study in irony.

Pink was used extensively as a color of protest following Trump's inauguration as the President of the United States in 2017. The landmark Women's March turned the capital city of Washington pink, with knitted caps termed p**syhats emerging as one of the movement's most striking symbols. As gender studies scholar Rebecca Jordan-Young told Time: "The ramped-up vocal misogyny of Donald Trump ... lots of women decided to own these symbols of femininity that had been grounds of disparagement." 

In political and historical contexts, white has long been a color of great significance. A symbol of purity, it became synonymous with women's empowerment when women of the suffrage movement co-opted it as a color of protest during the early 20th century. Modern politics has continued this legacy, with women leaders like Hillary Clinton and Kamala Harris marking major political milestones in statement white outfits. The Democrats, in particular, have integrated the color into their diplomatic appearances, such as at the annual State of the Union Address. 

A sea of white memorably flooded the SOTU assembly in 2019, where then-President Donald Trump delivered his speech before a Congress dominated by Democrat women wearing coordinated uniforms in solidarity with gender issues. As political expert David Barker told the Voice of America: "To [Trump], all the women sitting out there wearing white is just a big statement of opposition." 

White wasn't a Democrat-only color that day though, with Republicans like Tiffany Trump and Kimberly Guilfoyle also staking a claim to it by synchronizing with the theme. It was supposedly meant as a statement, which Guilfoyle spelled out on X, formerly Twitter: "Memo to Democrats: You don't own the votes of all women and you don't own wearing the color white!" The merit of her forceful assertion, however, was questionable since The New York Times reported that all the Republican women had also been invited to wear white. 

For Halloween 2019, Kimberly Guilfoyle dressed up as a witch. The talk show host did a fair job of it, putting together an ensemble of a pointy black hat and a figure-hugging black dress complete with purple detailing. It seemed like an ordinary enough getup, considering that a witch's costume was one of the most Googled Halloween costumes of 2019. However, Guilfoyle's outfit was far from conventional. It came with a dose of subtext, meant to be read in conjunction with the hunting outfit her boyfriend, Donald Trump Jr., was wearing. Together, the duo represented a witch-hunt — something Republican supremo Donald Trump claimed he was being subjected to at the time. 

Trump was at the center of a probe that investigated his alleged abuse of power to influence the U.S. elections via Ukraine, which led to an impeachment trial against him. "Witch-hunt" was a favorite term of the former president who used — or, as some would argue, overused — it to defend himself against the charges in public arenas. The rest of his family naturally followed suit, with his son and Guilfoyle making the most of Halloween for a hyper-realistic, too-literal interpretation of witch-hunt.

"With all the bullsh*t the Democrats are throwing out there we just couldn't resist," Trump Jr. wrote on Instagram, sharing pictures of himself in head-to-toe camouflage gear and a bow-and-arrow set, posing beside Guilfoyle. Trust the Trumps not to lose even a single opportunity to make a political statement! 

Kimberly Guilfoyle's enthusiasm for using her nationwide platform for the twin purposes of politics and fashion was more than evident throughout her run as a star campaigner for Donald Trump's presidential bid in 2020. Every appearance the former Fox News host made on Trump's campaign trail to rally support for her boyfriend's father made for a dramatic fashion moment. A memorable one, in particular, happened in Michigan, where she was headlining a Make America Great Again (MAGA) event with Donald Trump Jr. and Trump loyalist musician Kid Rock. For the occasion, Guilfoyle opted for an extraordinary ensemble comprising a plain black tee, an olive jacket, and a pair of jeans ripped at the knees. 

This extraordinariness didn't come from the outfit itself — a jeans and tee combo is hardly a novel idea, after all. What made it so momentous was Guilfoyle's decision to wear it, especially to a political event. Customarily dressed in taut dresses and pencil heels, Guilfoyle makes a rare show of dressing up as informally as she did in Michigan. Her oversized jacket and ripped jeans symbolized casual comfort that few other political figures have dared to indulge in during presidential campaigns. 

Kimberly Guilfoyle's tight fits and plunging necklines are by now as much a part of her public image as her firebrand Republican rhetoric. The fact that she is rarely ever out of her routine wardrobe makes for some interesting contrasts, especially around the holidays when the norm is to slip into something more traditionally festive. Consider, for instance, her choice of outfit in Christmas 2023. Guilfoyle opted for a short, black dress with a silver bow detail around the bust for the Trump family get-together at Palm Beach, Florida. Despite the daring of her holiday ensemble, Guilfoyle looked ravishing, as comments under her Instagram post made clear. 

Reactions hadn't been as kind in 2018, when Guilfoyle shared a poolside selfie from her seat at the Trump's Mar-a-Lago retreat. Her form-fitting black top was zipped down the front to show just enough skin to get social media users going about her unconventional holiday attire. Per usual, Guilfoyle's post turned into a combat zone between her staunch followers and the critics disapproving of her skin-baring turnout for Christmas day, as noted by Yahoo! News. While showing more skin when poolside is not unusual, Guilfoyle is a prominent public figure — and an extended member of the Trump family, no less — and thus held to stricter standards. 

When famous people make zealous public commitments to the cause of animal rights, it usually serves as an open invitation for their lifestyle choices to be scrutinized. And often, the scrutiny is so thorough that it leads to the discovery of contradictions that poke holes in their stories. In an interview with Impact Wealth magazine, Kimberly Guilfoyle made an impassioned show of her love for animals. "As a prosecutor in California, I was stalwart in my commitment to carry out justice for those with no voice. One of my greatest moments was when I fought and helped make animal abuse a felony," she said. A dog mom to three, she has lent her support to the cause of pet adoption and is also associated with the nonprofit Furry Friends. 

For all her noble efforts, Guilfoyle is still known for having some animal-derived items in her wardrobe — something that awkwardly puts her at odds with her social causes. Back in 2019, the former attorney was spotted out and about in New York City bundled up in a $1,300 parka trimmed with fox and rabbit fur, the Daily Mail reported. Guilfoyle's preference for leather, meanwhile, is also no secret. From jackets to pants to boots, she has a fair amount of leather pieces.