Kimberly Guilfoyle Wore Some Seriously Bad Outfits In 2024

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There is one figure in the Republican party who loves attention, and no, it's not Donald Trump. We're talking about Kimberly Guilfoyle, once a political adviser to the president-elect as well as arm candy and almost-wife to Donald Trump Jr., though rumors of an affair have left many wondering how long their relationship will last. Guilfoyle has a wonderfully bad habit of wearing outrageous outfits, oftentimes making the party of family values shake its head when she steps in front of cameras in yet another mini skirt or cleavage-baring dress. And with 2024 being an election year, Guilfoyle had plenty of time to trot out her worst outfits, with no shortage of podiums, fundraisers, and political gatherings to show herself off at.

While her bad outfit history seems to be a recurring trait, some credit must be given to her sheer consistency. In a way, we're thankful, because we always have something to write about. So, as we close out 2024, we're taking a look back at some of her best worst wardrobe choices. And with Trump headed back to the White House in 2025, we will be sure to be on fashion watch for whatever bombshells the unflappable Ms. Guilfoyle is ready to bring us in the new year.

Kimberly Guilfoyle brought in 2024 with a still-up Christmas tree and a very short Retrofête dress that likely confused Santa when he made his naughty or nice list. Paired with a cream-colored pair of Paris Texas over-the-knee boots, Guilfoyle clearly came to make a statement. That statement is likely that she's a little overdressed for what looks like a living room and would perhaps be more at home at a University of Texas fraternity holiday party. But hey, she chose to start the year with a bang and we shouldn't judge her for it.

We're not sure if the cross-armed pose is supposed to be sexy or imply that it's cold out, but we do know that the aged American flag in the background looks like it's made out of wrapping paper. The location of Guilfoyle's Instagram photo of her 'fit is tagged as the Pine Creek Sporting Club, which according to its website is a members-only hunting and target shooting club. And while we don't want to judge what people like to wear to hunt, one has to wonder if Guilfoyle once again wore the wrong outfit to the wrong event. 

In March, Kimberly Guilfoyle hosted a fundraiser for Abraham "Abe" Hamadeh's congressional race at none other than Trump HQ, Mar-a-Lago. And while the goal of any political fundraiser is a memorable evening that spotlights the person you want to win, Guilfoyle's revealing outfit almost stole Hamadeh's thunder. Though the incoming Congressman would go on to win his race, people were not happy with Guilfoyle's black dress and its plunging, cleavage-flashing mesh neckline and mesh slit up the thigh. For his part, Hamadeh did not seem to have a problem with it though, as he posted photos of himself next to Guilfoyle on his own Instagram account.

After Guilfoyle posted a video of her speaking at the fundraiser on her Instagram, the comments lit up with people telling her to show less skin, with users saying, "Cover up, [it] would be more professional;" "Yikes!!! No clothes (hand slapping face emoji) What is this about????" and more pointedly, "Girl looks like she fell off a stripper pole." But if there is one defining trait of a classic Kimberly Guilfoyle outfit, it's that she truly never ever cares what other people think about it.

For Alina Habba's 40th birthday, Kimberly Guilfoyle decided to bring the party to her party and arrived looking like a glittering, yellow disco ball. It's not known if there was an official theme, but Page Six reports that Habba, who has served as Donald Trump's lawyer, was dressed to match the orange and brown Hermes gift bags that were on hand. One wonders if both she and Guilfoyle were trying to imitate inanimate objects, and as one commenter on X, formerly known as Twitter, noted — Guilfoyle kind of looked like a bathroom tile backsplash.

There's also the chance that Guilfoyle was going for something along the lines of a Gustav Klimt painting, but with the shimmering squares wrapped around her like a towel, we unfortunately cannot give her the benefit of the doubt. Per usual in 2024, she attended the event with Donald Trump Jr., who wore his requisite navy blue everything, creating a jarring dissonance between Guilfoyle's shimmering Daft Punk homage and his just-another-day-at-the-office look.

News personality, former prosecutor, and now children's book author — Kimberly Guilfoyle can do it all, and she will wear whatever she wants while she does it. In May, to break the news that she had published a children's book titled "The Princess & Her Pup," Guilfoyle posted a photo to Instagram of her posing with the book while wearing a flashy, strapless, semi-see-through, and sequined white dress.

The children's book was published by a company called Brave Books, whose website says it is a "Christian publishing company that makes books for kids that reinforce biblically-based, foundational values." And while Guilfoyle's white dress isn't exactly sinful, internet speculators were wondering, yet again, why she chose to wear something so eye-catching when the point of the announcement was aimed at promoting something for children and parents. Guilfoyle captioned the post by saying her book tells "a wholesome and heartfelt story about the importance of friendship and the value of courage. Together, we can all bring more positivity, joy, and grace into this world." That may be true, but Guilfoyle may want to find a more wholesome outfit for her next book.

In July, Kimberly Guilfoyle and Donald Trump Jr. took their support of his father, Donald Trump, across the Atlantic, where they raised money for the America First Policy Institute, a conservative-leaning nonprofit. There Guilfoyle debuted a short, printed Balmain mini dress, which retails for $2,432. Guilfoyle sported the high hem in 40-degree weather, proving that she is more than willing to suffer for fashion, and not just at the hands of Internet commenters telling her to please dress more appropriately.

But the pricey outfit was worn for a price, with The Guardian reporting that event attendees had to shell out as much as $100,000 per couple to meet with Guilfoyle and Trump Jr.; $25,000 for a photograph with Trump Jr., Guilfoyle, and her black-and-white print dress; and a meager $10,000 just to get in the door. In many ways, this outfit is the pinnacle of Guilfoyle's wayward fashion choices. Needing a fancy outfit to wear to a fancy fundraiser, she tried to pull off couture and ended up looking like a printed rug. Guilfoyle's style choices are a wonderful reminder that history can and will repeat itself, and we are looking forward to whatever bad outfits she entertains us with in 2025.