Kimberly Guilfoyle’s rise and fall in Trump land has emboldened her social media activity. Guilfoyle, whose relationship with Donald Trump Jr. ended in 2024, recently took time out from flaunting her tacky outfits to throw shade at the Trump family circle. Taking to Instagram, Guilfoyle showed off her photoshop skills in a slideshow highlighting her summer adventures and colorful, overly frilly wardrobe. However, she managed to sneak in what could be perceived as a dig at the Trump family. “From the thrill of the Monaco Grand Prix to celebrating Chris and Lea’s beautiful wedding in Italy, this summer has been a reminder of God’s blessing and the power of surrounding yourself with good, purposeful people,” she captioned the post.
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The US Ambassador to Greece. pic.twitter.com/zx4z8HlB1y
— Ron Filipkowski (@RonFilipkowski) June 21, 2025
Whether Guilfoyle meant that members of the Trump clan weren’t “good, purposeful people” like her new crew remains to be seen. However, one constant with Guilfoyle is her ability to garner attention for her over-the-top outfits. On X, for example, users have been having a field day over her gown with puffed sleeves, a translucent lace skirt, and a fire engine red bodice, a photo of which she included in her airbrushed Instagram roundup (to the tune of over one million views). “Why do they dress like Capital Citizens from The Hunger Games?” asked one user. A second wrote, “She looks more like the lead guitarist from KISS.” Meanwhile, a third post read: “Such an utter embarrassment. I really thought she was going to go back to her earlier days of looking classy when she went to Greece. Guess not.”
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There also seemed to be confusion over whether the guy in the photo with her was an employee or a love interest, but it was her son, Ronan Anthony Villency.
Kimberly seems just as devoted to Donald Trump as ever
Kimberly Guilfoyle might have shaded the Trump clan with her most recent Instagram post, but the likelihood of Donald Trump receiving any of her ire continues to seem reasonably low. Judging from her social media activity, she is just as devoted to her party leader as she’s always been. For example, she went deep into her archives for the best of her photos with Donald to wish the president a happy birthday on June 14th. “Born on the day we celebrate the Stars and Stripes,” she captioned the Instagram post. “Thank you for always putting America first. Happy birthday, President Trump!” This despite reports that Donald did not approve of Guilfoyle’s inappropriate outfits when she was dating his oldest son.
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Guilfoyle’s continued devotion to Donald isn’t all that surprising considering it was him who gave her the cushy ambassador job in Greece — conveniently around the time that her relationship with Donald Trump Jr. ended. While Guilfoyle did engage in some post-split revenge dressing, in December 2024, she seemed excited about her new role. “I am thrilled to have the opportunity to carry this message abroad as the next United States Ambassador to Greece,” she said on her Rumble talk show (via The National Herald). “I look forward to earning the support of the U.S. Senate and working with our key Greek allies to strengthen the bilateral partnership and promote energy, security, peace, and prosperity.”
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Of course, Guilfoyle also snuck in gushing comments about Donald during the segment. “I feel deeply honored to serve as U.S. Ambassador under the greatest president this country has ever seen,” she said at the time.
