Kimberly Guilfoyle just proved that looking good is the best kind of payback.
The former Fox News host and ex-fiancée of Donald Trump Jr. stepped out in a fabulous black dress at a charity gala in Palm Beach, making sure all eyes were on her. Meanwhile, Donald Trump Jr.’s ex-wife, Vanessa Trump, has also been making headlines- reportedly dating none other than golf legend Tiger Woods.
As the exes move on in their own ways, Guilfoyle’s bold fashion choice at the Wags to Riches gala certainly got people talking. Dressed in a frilly black gown with a plunging neckline, she was seen posing confidently with Hollywood star Kelsey Grammer, stealing the spotlight and sparking plenty of online chatter.
A Bold Statement At A Star-Studded Event
The event, held in Palm Beach, Florida, drew a mix of political figures and Hollywood elites, raising funds for animal rescue efforts. While it remains unclear if her former fiancé and his current partner, Kimberly Guilfoyle’s predecessor Vanessa Trump, were in attendance, the close-knit Palm Beach social scene made it likely they weren’t far away.
Kelsey Grammer with Kimberly Guilifoyle at Mar-a-Lago this weekend pic.twitter.com/FKvOitKjY3
— PatriotTakes 🇺🇸 (@patriottakes) March 23, 2025
Fans quickly noticed her polished appearance, with social media users commenting on her glowing look post-breakup.
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“Leaving Trump Jr. has had a wonderful effect on Guilfoyle,” one fan remarked.
Leaving Trump Jr. has had a wonderful effect on Guilfoyle.
— Maxine, Duchess of Survival 💪🏽🌻🌹💙 (@Maxine2xs) March 24, 2025
Another noted, “Her makeup is better than usual, and she has a genuine smile for once.”
I think it's her…her makeup is better than usual and she has a genuine smile for once.
— Renee ☮️🦋🦉 (@DidesideroRenee) March 24, 2025
Guilfoyle’s appearance alongside Grammer fueled speculation that she is enjoying a fresh chapter post-breakup. The former prosecutor and ex-wife of California Governor Gavin Newsom has maintained a high profile over the years, but this latest public outing showed her in a new light.
The Miami Herald described her outfit as a “frilly black gown with a plunging neckline,” reinforcing the notion that she was making a statement. With the media and fans dissecting every detail of her post-breakup transformation, Guilfoyle seems to be embracing the attention.
Whether intentional or not, her latest look left an impression. If this was, in fact, a “revenge” dress, it certainly did its job- capturing headlines, sparking conversations, and reminding everyone that Kimberly Guilfoyle knows how to make an entrance.
Also Read: Donald Trump Jr. Drops Unexpected 2-Word Reaction To His Ex-Wife Dating Tiger Woods
