Kimberly Guilfoyle Won't Ever Live Down Her Inappropriate Charity Event Dress

Kimberly Guilfoyle leaned into the shock factor when she attended the Wags to Riches Gala at President Donald Trump's Mar-a-Lago resort in Florida. The fundraising event, geared at providing support for animal rescue and welfare, was held in March 2025. Holding nothing back, Guilfoyle opted for a dramatic, black gown featuring a plunging neckline, with sheer, lace paneling along the corset and a long, black train.

Guilfoyle showed off her daring look in a carousel of photos on Instagram, posing with her son and other event guests. While people lauded her efforts to care for animals, others were uncomfortable with how dramatic her dress was. "Why do you always have to show your body parts good grief?" someone commented. Others made mention of the fact that Guilfoyle's fiancé, Donald Trump Jr., wasn't in any of the photos. In fact, Guilfoyle and Trump Jr. had split up around December 2024, when he was seen out with socialite Bettina Anderson. People hinted that Guilfoyle was so outrageously dressed because she wanted to give Trump Jr. a glimpse of what he was missing. "Eat your heart out DTjr," another wrote in the comments. "Revenge look," another added, including clapping emojis. This wasn't the only time Guilfoyle dressed for revenge. There's a whole list of Guilfoyle's outfits that screamed revenge after her split from Don Jr. The only problem is that many of Guilfoyle's outfits are beyond tacky, and she can't seem to stay away from outdated trends — this plunging dress being one of them.

Kimberly Guilfoyle made a similar fashion faux pas at a later date. Guilfoyle was sworn in as the U.S. Ambassador to Greece in September 2025, a nomination made by President Donald Trump. To honor Greece, Guilfoyle attended the Hellenic Initiative's Gala in London in October 2025 to mark her position as the newly-appointed ambassador. Only months after her plunging black dress that she wore to the Wags and Riches Gala, Guilfoyle attended this gala in a hot red mini dress covered with sheer fabric. She just can't ditch that sheer overlay trend.

In photos from the event, posted to Instagram by Guilfoyle herself, the new ambassador sticks out like a sore thumb. Her bright red color certainly feels representative of Donald Trump's MAGA circle, but not related to Greece in any way. Not only that, but Guilfoyle's choice in wearing a micro red dress covered by sheer fabric gave her outfit a tacky, unprofessional finish. It lacks the polish and elegance we'd hope to see from a new ambassador. Her dress came off as disjointed and cheap, as if she's trying too hard to look hot. And even at this event, months after Guilfoyle and Donald Trump Jr.'s separation, people still hinted that she was wearing something provocative as a form of revenge. "I just wanted to add it's Donald [Jr.'s] loss," someone commented. It seems that revenge dressing is hard to resist.