Kimberly Guilfoyle's Most Inappropriate Outfits Ever

Kimberly Guilfoyle has undergone a dramatic transformation over the years — and she's made a few fashion missteps along the way. When Guilfoyle was married to Gavin Newsom, a 2004 Harper's Bazaar profile likened her to one of America's classiest and most fashionable first ladies, Jackie Kennedy Onassis. Newsom was mayor of San Francisco at the time, and Guilfoyle was hosting the Court TV series "Both Sides."

Her marriage to Newsom didn't last, and Guilfoyle later landed a co-hosting job as one of the panelists on the Fox News show "The Five" and began dating Donald Trump Jr. in 2018. Interestingly, one of her favorite designers since entering Trumpworld has been Chiara Boni. Boni isn't the type of clothier who will ask public figures not to wear her apparel if she disagrees with their politics, but she did tell BoF that she identifies as "liberal." Stylist Lauren Rothman suggests that women like Guilfoyle are drawn to Boni's garments because they feature tailoring that flatters the figure. Many of her designs are also bright and monochromatic, so they photograph well. They're safe options that don't show a lot of skin, which is something Guilfoyle did often when working in the fashion industry.

Guilfoyle modeled while attending law school, telling People in 2014, "It ended up being a great way to pay for it." One of her jobs was posing in lingerie for Victoria's Secret. While she doesn't publicly wear anything quite as revealing these days, there have still been complaints that her outfits are inappropriately revealing.

The sequins on Kimberly Guilfoyle's Balmain mini dress glimmered merrily in the bright lights of the Admirals Cove Street Fair, but they looked somewhat out of place. In December 2023, Guilfoyle visited the Jupiter, Florida, carnival with Donald Trump Jr. She later shared her outfit deets on Instagram, revealing that her platform sandals with towering heels were Louboutins. She looked more club-ready than eager to ride the Ferris wheel with her sweetie. And based on Donald Jr.'s outfit, the couple hadn't dashed straight to the fair after attending a swanky dinner at Donald Trump's Mar-a-Lago beach club. The son of the four-time indicted former president was dressed down in a long-sleeved mint polo shirt, jeans, and sneakers.

Guilfoyle also shared the photos on Facebook, where some amateur fashion critics voiced their opinions of her impractical apparel. "At least Don Jr knows what is appropriate attire for a carnival with the kids," one person wrote. "Her hair gets longer 2and her skirts get shorter," another commented.

Short skirts were essentials in Guilfoyle's Fox News wardrobe repertoire. According to The Washington Post, it was no accident that she was always sitting where viewers could get a clear view of her legs on "The Five." According to the outlet, two sources recalled former Fox News CEO Roger Ailes looking at an image of said view and saying, "There's Kimberly, doing her job."

When attending events where cameras are sure to be flashing away, it's usually a good idea to avoid thin fabrics that are stretched taut over the body. Actor Kristen Bell told People that she even has her stylist take snapshots of her outfits before she hits the red carpet to ensure that they don't become see-through when photographed. Kimberly Guilfoyle could have benefitted from this advice when she attended Zang Toi's fall 2019 show during New York Fashion Week. For the event, she wore a tight black dress with fabric butterflies on the sleeves. The insects would have been the focal point of the garment — if it wasn't so sheer. We're guessing she was unaware that bright light would make her bra underwire and the waistband of her shapewear or pantyhose visible when she chose the dress.

Guilfoyle experienced a similar problem when she attended The New York Society for the Prevention of Cruelty to Children (NYSPCC) Food & Wine Gala in 2016. She was wearing a blue jersey dress that revealed a bit too much when photographed — making it entirely inappropriate for the event in question. It looks like she even blurred the skintight garment's bust area before she tweeted a photo of it. 

Entertainment icon Bette Midler has poked fun at Guilfoyle for favoring tight dresses. "Kimberly Guilfoyle was the highlight of the #RNC," she tweeted in 2020. "I loved her red dress. I wonder if it comes in her size?"

Kimberly Guilfoyle stood out in family photos from Tiffany Trump and Michael Boulos' November 2022 wedding. Guilfoyle's fundraising kept her future father-in-law's re-election campaign in the black, making her a big asset for the Trump family. However, her black dress with dramatic puff sleeves and a high-low skirt was not a big hit on X. "Give poor Kim a break. She was running late and didn't have time to change out of her usual vampire gear," one tweet read. Lara Trump, Marla Maples, Melania Trump, and Ivanka Trump were all wearing pale colors such as lavender and powder blue in a picture with the bride. Of Guilfoyle's dissonant dress, fashion consultant Amanda Sanders told the New York Post, "It looks witchy, like a costume." Some X users suggested Kimberly's color choice explained why Ivanka cropped her out of the wedding photo when she shared it on her Instagram account. However, a source told the Daily Mail that there was no sartorial snub; Ivanka had just made "a terrible mistake."

InStyle consulted three experts about whether it's appropriate to wear black to a wedding, and their consensus was that it's usually acceptable. However, some cultures might find the color offensive because it represents mourning. There are also some unwritten rules. "If you're attending a beach wedding, then I recommend going for brighter colors," said stylist Gillian McHattie. Tiffany's wedding was at her dad's Mar-a-Lago beach club, which may explain why the other women avoided dark colors.

In honor of women's suffrage, Democratic lawmakers wore white for Donald Trump's 2019 State of the Union address. Curiously, so did Kimberly Guilfoyle and Tiffany Trump. Guilfoyle's body-hugging dress, which featured knotted detailing on the neckline and at the waist, was designed by Tom Ford. On her feet, she wore white Manolo Blahnik pumps.

Guilfoyle didn't leave people wondering for long whether she had discovered some common ground with Democrats. She took to X to reveal that her dress choice was more about trolling her enemies than celebrating women gaining the hard-won right to vote. "Memo to Democrats: You don't own the votes of all women and you don't own wearing the color white!" she wrote. She then reaffirmed her allegiance to Donald Trump. But maybe using a Tom Ford design to stake her claim on the color wasn't the best decision. In a 2017 appearance on "The View," Ford said he was a Hillary Clinton supporter. He also told Elle that he doesn't think his clothes are the right fit for any presidential couple because they're not American-made. "They're very, very expensive. I don't think most women or men in our country can relate to that, and I think the First Lady or the President should represent all people," he added. So, he kinda admitted that wearing his clothes can make political figures — like Guilfoyle — seem a bit out-of-touch.

In 2023, Donald Trump Jr. posted a photo carousel on Instagram chronicling a fishing trip with Kimberly Guilfoyle, her son Ronan, and Trump's son Spencer. The guys were clad in shorts and long-sleeve shirts, but Guilfoyle had on a black maxi dress with a plunging neckline. "A dress Kimberly really?" one of Trump's followers wrote. "Why is she in a funeral dress lol," another commented. But apparently, her apparel didn't impede her angling, as she was pictured posing with a fish she caught.

This isn't the only time Guilfoyle was criticized for choosing questionable clothing for an outdoor trip with her fiancé. In 2022, she joined Trump for Louisiana Attorney General Jeff Landry's 12th Annual Gator Hunt. After either Trump or Guilfoyle shot and killed a small alligator, they posed with their bloody trophy. In a photo that Trump posted on Instagram, Guilfoyle had a gun in her hand — and high-heeled boots with blood-red Christian Louboutin soles on her feet. "Nice hunting shoes she is wearing! What a joke!" tweeted one X user who noticed her footwear. "She didn't go hunting in those expensive, pristinely clean boots. They can't even fake it well," another critic wrote. Ruining a pair of boots with a little mud and blood probably wouldn't phase Guilfoyle, who once told Us Weekly of her shoe collection, "There have been estimates of about 500 pairs. Is that more than Imelda Marcos? I think it is."

In a 2023 interview with Impact Wealth, Kimberly Guilfoyle touted the prosecution work she did in San Francisco. "I was stalwart in my commitment to carry out justice for those with no voice," she said. "One of my greatest moments was when I fought and helped make animal abuse a felony." The publication also mentioned that Guilfoyle was working on a children's book in which animal rescue would figure into the storyline somehow and that she fundraises for the Furry Friends charity in Jupiter, Florida. But while kitties and certain canines might benefit from Guilfoyle's generosity, she wasn't squeamish about wearing the skins of close cousins of the doggies that she works to save.

In 2019, the Daily Mail published photos of Guilfoyle wearing a $1,300 Nicole Benisti coat. The garment was lined with genuine fox and rabbit fur, and she was wearing the hood pulled up to show off its thick fur trim. "What the f**k did the bunny and fox do so wrong to be killed and made into an ornament, aka, accessory to a coat???" read one reaction to her garment on X. "Disgusting!!!!" And while Guilfoyle might not be wearing puppy pelts while singing Donald Trump's praises, she has been compared to "101 Dalmatians" villain Cruella de Vil on X quite a bit.

Kimberly Guilfoyle made a bold attempt at pulling off the Barbiecore trend for her 55th birthday party, but her look fell flatter than Barbie's feet when her heel pads hit the pink sand for the very first time. Instead, Guilfoyle looked like she was trying to make MTV's "My Super Sweet 16" great again in a strapless mini-dress covered with bright pink spangles. However, a user on X probably wasn't referring to those shiny, decorative disks when they responded to a photo of Guilfoyle and some friends by tweeting, "More plastic than a Mattel factory." The former Fox News host clung to Barbie's pre-existential crisis persona by keeping her own arches far away from the floor in silver platform sandals. She finished her look with a pair of coordinating statement earrings.

At least one Instagrammer thought Guilfoyle didn't look like she was trying to relive her teenage years. "Kimberly needs to stop dressing like a 22yr old," they wrote. But don't be fooled by her flashy outfit — the night was not all about her. Donald Trump showed up and turned his heartfelt speech for the birthday girl into a xenophobic rant. "We have millions of people pouring in from mental institutions, from jails ... including many, many terrorists," he can be heard saying in a video. So, you can see why Guilfoyle had to try so hard to keep the spotlight on herself.

Kimberly Guilfoyle was supposed to be helping Arizona congressional hopeful Abe Hamadeh with his campaign at a political event. Still, all some people seemed to notice was her questionable outfit choice. She had on a little black dress with a side slit that went all the way up to the hip and a plunging neckline that revealed a lot of cleavage. Perhaps she believed the sheer mesh inserts covering the two revealing openings made the garment more tasteful. However, they did not prevent her from being a distraction as she stood on the stage behind Hamadeh.

It was Hamadeh's moment to shine — he'd made it to the MAGA big time by scoring an invite to speak at Mar-a-Lago. But the fashion police clearly cared more about Guilfoyle's perplexing outfit decision than the policies he was describing. It probably didn't help that Guilfoyle was in the center of the photo Hamadeh shared on his X account. One person observed, "Damn, she really just putting those things out there." Another described Guilfoyle as "wanna-be Elvira." But give the gal a break — perhaps she's just trying to get more mileage out of her party dresses because her future hubby is worried about the Trump family's financial future. They may all have to start selling off their wardrobes to help Donald Trump pay his $450 million civil fraud judgment.