Kimberly Guilfoyle’s Most Memorable Wardrobe Malfunctions Ever

Once a voice for justice in the courtroom as an attorney, Kimberly Guilfoyle has become mainly a spokesperson for former president Donald Trump’s re-election campaign. As the fiancée of Trump’s eldest son, Donald Trump Jr., Guilfoyle has devoted her social media and podcast to criticisms of President Joe Biden’s administration and MAGA rallying cries.

The former Fox News host has also become known for her distinctive personal style, which has led Guilfoyle to pick some inappropriate outfits over the years. Too-low necklines, too-cutesy baby-doll dresses, and too-distracting colors and cuts for official events have elicited plenty of criticism.

Every woman has suffered an occasional wardrobe malfunction, but Guilfoyle’s style choices make her more vulnerable to them than most. Ride-ups, slip-downs, and see-throughs are among her standout moments, and since she is such a visible part of the Trump team, this only adds to the embarrassment factor.

Former Fox News personality Kimberly Guilfoyle and businessman Donald Trump Jr. had just started to go public with their relationship when they attended the Zang Toi exhibition at New York Fashion Week in early 2019. Naturally, Guilfoyle wanted to look her best for the occasion, and she almost succeeded. Almost.

The silhouette of the black dress that she chose for the occasion was flattering, and the embroidered butterfly detail on the left shoulder strap added a pop of whimsy. Alas, Guilfoyle apparently got dressed in a dim room before the event. Under the bright lights of the venue, the mesh bodice of the dress became rather see-through, illuminated her chest, and made it quite clear exactly what was underneath. A friendly word of advice for Guilfoyle for next time: It’s usually best to match the darkness of one’s undergarments and outerwear.

In an October 2023 episode of her self-titled “Kimberly Guilfoyle Show” on the Rumble platform, Guilfoyle’s message was obscured by her apparel. Her bright yellow dress was eye-catching enough—blinding, even—but its low-cut neckline was distracting in more ways than one. Even Guilfoyle seemed self-conscious of her exposure; the camera caught her pulling up the top and squeezing her shoulders together as if to cover the excess cleavage.

Kim wore a special outfit for guest Roger Stone today, but has been struggling to keep things under wraps. pic.twitter.com/GHxDQyNKP3

— Ron Filipkowski (@RonFilipkowski) October 5, 2023

Frequent Trump critic Ron Filipkowski posted a clip of the interview on X, formerly known as Twitter, noting she was “struggling to keep things under wraps.” Plenty of followers found the look unappealing, too. “Zero self-awareness. Tacky,” said one. Commented another, “She paid a lot for those, she wants to show them off.” Another put it more directly: “If you have to occasionally adjust your shirt to keep “the girls” from falling out, then your choice of shirt is too low for TV. What happened to dressing classy instead of trashy?”

Understandably, Guilfoyle enjoys showing her figure to her best advantage, which often means wearing close-fitting dresses. However, as anyone who has donned a tight skirt knows, one has to move carefully. In June 2018, when Guilfoyle and Donald Trump Jr. were a newly loved-up couple, paparazzi caught them on their way to a midtown Manhattan restaurant. Photos shared by the Daily Mail showed the two exiting a town car—along with a little too much of Guilfoyle. In one shot, it was clear the skirt of her orchid-toned dress had ridden up almost to the top of her thighs. The then-Fox News host began tugging it down, and Don Jr. helped her adjust it to its proper length. Guilfoyle also appeared to be adjusting the neckline, as well.

The two became engaged two years later, but only made the engagement official in 2022 when Guilfoyle showed off her sparkler in an Instagram pic celebrating her fiancé’s New Year’s Day birthday. Lately, though, there have been signs Guilfoyle and Trump’s relationship is on the rocks, not least of which is their apparent reluctance to set a wedding date.

Finally, the vote for the most embarrassing wardrobe malfunction goes to Kimberly Guilfoyle’s outfit on the final night of the 2024 Republican National Convention. The red sheath dress featured a matching shrug that covered her usually-exposed décolletage, and the below-knee length was appropriately conservative. However, when Guilfoyle walked to her seat in the VIP box at Milwaukee’s Fiserv Forum, she had to pull up her skirt in order to sit down, and her hand lingered longer than one might expect. The gesture was, unfortunately, caught on camera; even more unfortunately, it looked as though Guilfoyle was doing something quite indelicate.

What is Kimberly Guilfoyle doing in this video?

😳😬😳😬😳😬😳😬😳😬😳😬😳

pic.twitter.com/0Q372fMJrB

— Art Candee 🍿🥤 (@ArtCandee) July 19, 2024

X user Art Candee was among the commenters who caught and posted the embarrassing moment online. Rumors flew in response: “Dealing with the disease of the week?” queried one. A second suggested, “It looks like her Spanx crotch has slipped down and she’s pulling it back up—at least I hope that’s what that is.” To add insult to injury, Donald Trump Jr.’s lackluster reaction to Guilfoyle’s speech only fed the speculation their relationship is faltering.