Kimberly Guilfoyle's Bold Skin-Baring Gala Dress Was The Ultimate Middle Finger To Don Jr.

Kimberly Guilfoyle has been frequently accused of wearing inappropriate outfits. Among her wide range of fashion mistakes, one of the most oft-repeated is that Guilfoyle's garb is too revealing. At the 2025 amfAR Gala in France, Guilfoyle donned one of the many skin-baring gowns in her closet. Granted, showing some skin is common at galas, but Guilfoyle took her look farther than many other guests. The glowing red fabric was an attention-getter, and one lace panel extended high up Guilfoyle's thigh. The other panel spotlighted most of Guilfoyle's chest, with a thicker lace concealing part of one breast.

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Clearly, this dress is a new favorite since she wore it as part of a spread in the April 2025 issue of Metropolitan Palm Beach. At the time, Guilfoyle shared a pic on her Instagram account. However, the dress didn't look quite as revealing, since the bottom was cropped out and her lengthy hair extensions covered most of the lace on her chest. Guilfoyle also made waves on the cover, since she was wearing Donald Trump Jr.'s former engagement ring (albeit with a more conservative coral suit).

Lately, Guilfoyle seems to be making all sorts of gestures regarding her old flame, including wearing this red gown. Although it's been claimed their split quietly happened months before it became public, there've been many signs it was a messy breakup. One reportedly contentious area for Don Jr. was Guilfoyle's wardrobe. "The tight dresses need to go and she has been told that," an insider relayed to People in December 2024, shortly before their breakup was reported by the outlet.

As she noted in her Instagram post about her magazine feature, Kimberly Guilfoyle's red dress was designed by Oscar Lopez, a designer who won the "Project Runway" spinoff "Under the Gunn" back in 2014. Lopez has also dressed other members of the Trump family, like Lara Trump, for years. Although Guilfoyle is no longer tied to the Trumps since her breakup with Donald Trump Jr., she's made it clear that her sartorial loyalties remain with Lopez. For better or worse, Lopez and Guilfoyle seem to share a similar aesthetic when it comes to dresses — make them as vibrant and skin-baring as possible. Lopez also created one of Guilfoyle's gala looks from April 2024, an intensely yellow gown that was one of her worst outfits that year. Besides being super-low cut, the fringed material was very see-through and looked like a beaded curtain rather than a gown. 

In addition to her red dress, Guilfoyle showcased another Lopez creation in Metropolitan Palm Beach magazine: a lace black ballgown adorned with feathers. Not surprisingly, this dress had a neckline that plunged to mid-chest, and lots of transparent parts on the bodice. Clearly, this one's also a favorite for Guilfoyle, since she wore it to the 2025 Wags to Riches Gala. 

However, not everyone sees Guilfoyle's fashion choices as an expression of newfound freedom. "Did she expose herself to stay relevant!" griped one Facebook poster. "Who cares, she was no one without Trump and she will quickly become no one again, now that it's over!"