Kimberly Guilfoyle has been letting the risque dresses fly since splitting from Donald Trump Jr. Even though it was reported Guilfoyle’s inappropriate outfits were an issue with Trump, she has been unafraid to flaunt them after the two went their separate ways. On March 23, the former Fox News anchor posted/reposted snaps and videos from a charity event held at Mar-a-Lago to raise money for Furry Friends, a no-kill animal rescue organization based out of Jupiter, Florida. For the fundraiser, Guilfoyle rocked a cleavage-baring black dress with a lacy bodice and plunging neckline. To further accentuate her assets, she accessorized with a chunky Y-necklace with pendants that dangled down the front of her chest. The dress also featured a frilly black skirt and a belt adorned with a bow. Naturally, Guilfoyle sported her trademark lengthy hair extensions and heavy eye makeup to complete the look.
On her Instagram Stories, the political pundit reposted a snap of her posing alongside her designer friend Oscar Lopez, who color-coordinated with Guilfoyle in a black tux. There were also a few clips Guilfoyle reshared to her Instagram Stories that showed her speaking to the charity event crowd in her low-cut dress. Plus, Guilfoyle offered a full-bodied view of the outfit in a photo of her posing outside next to her son.
That event was not the first time she rocked a spicy outfit at a Mar-a-Lago fundraiser. Guilfoyle wore a wildly inappropriate dress at Trump National Golf Course in November 2024, which was also a charity event for Furry Friends. On that day, she opted for a tight-fitting hot pink minidress that had a plunging neckline with diamanté lining. As mentioned, Guilfoyle continued to push the limits of decency into the next year.
Kimberly Guilfoyle’s spicy dress tour
The Mar-a-Lago charity event ensembles were tame compared to the busty dress Guilfoyle wore at the inauguration festivities in January. Perhaps it was because she knew Donald Trump Jr. and his new girlfriend would be in attendance that the Rumble media member turned up the heat at the political event. For one inauguration ball look, Guilfoyle wore a floral print dress that put her assets on display with its scooped neckline lined with blossom appliques. Somewhat surprisingly, her hair was relatively reserved for that event, but the look did seem too spicy for a political ball.
A month later, she continued to ignore fashion decorum when Guilfoyle attended a charity event in a gaudy minidress that was too tiny for the occasion. It was at the Old Bags Luncheon, where designer bags were resold to raise money for charity. Guilfoyle made an appearance in an Instagram carousel shared by fellow attendee Alana Stewart. The first slide showed Stewart posing alongside Guilfoyle, who wore a pink minidress with a chain link overlay and a high hemline. By Guilfoyle’s standards, this ensemble was not overly revealing, but she stood out next to the other attendees, many of whom opted for pantsuits or long, flowing dresses.
Guilfoyle’s tiny dress tour was far from over, as she celebrated her birthday with a big blowout party a few weeks later in March. While celebrating another trip around the sun, Guilfoyle looked single and ready to mingle in a body-hugging gold minidress that flaunted her curves. She showed off the look — and her matching handbag with gold straps — in an Instagram carousel that included pics with her friends.
