Kimberly Guilfoyle's Sheer Lace Dress Is Inappropriate For Her Ambassador Job
After being dumped by Donald Trump Jr. over her party girl ways and terrible fashion choices, you'd think Kimberly Guilfoyle would have taken the hint and finally toned down her provocative outfits — especially now that she's meant to behave professionally as the U.S. ambassador to Greece. But she obviously hasn't. At a January 2026 dinner with Greece's Prime Minister Kyriakos Mitsotakis and businessman Nikolas Tsakos, Guilfoyle once again confused a formal meeting for the nightclub, wearing a risqué outfit that left little to the imagination.
As seen on X, Guilfoyle wore a sheer, black dress that exposed part of her cleavage. Her hair was parted in the middle, and she rocked her signature bold makeup. "Still dressing like a hoochie," one user replied in the comments. Another slammed the former Fox News anchor for being shameless and unprofessional. "Dress with class, tacky," they said. "Are you trying to get your next man?" As always, Guilfoyle seemed completely unbothered by the comments, proceeding to upload a photo of herself with Israel's president, Isaac Herzog, on her socials.
And it seems like X users aren't the only ones put out by Guilfoyle's fashion sense. "Don Jr. has been telling people for months that Kim is so uptight and always dresses so professionally in these kinds of dresses and high heels," a source with knowledge of Don Jr. and Guilfoyle's split informed People in 2024. "[She] never looks relaxed or casual. The tight dresses need to go and she has been told that."
In defense of Kimberly Guilfoyle
Despite her role as U.S. ambassador to Greece, Kimberly Guilfoyle clearly hasn't fully retired her love of gaudy ensembles and flashy mini-dresses. Although, to be completely fair, she's made better fashion choices, if only occasionally: At the signing of an agreement deal between Greece and Ukraine in Athens, for example, Guilfoyle looked professional in an all-black pantsuit while posing with foreign leaders and entrepreneurs for a photo op. She also dressed suitably for a closed-door meeting with EU commissioner Apostolos Tzitzikostas to discuss policy matters. For that meeting, she wore a white pantsuit over a stylish black silk top with a ribbon collar. Still, though, her MAGA makeup and ugly hair extensions could have used some improvement.
Increased connectivity doesn't just bring us together, it makes us safer and strengthens our economies. I welcomed the opportunity to discuss with EU Commissioner @tzitzikostas America's priorities in the transportation and infrastructure domains. Greece plays an outsized role... pic.twitter.com/1qMpjSN94T
— Ambassador Kimberly Guilfoyle (@USAmbassadorGR) December 16, 2025
In contrast, Guilfoyle repeatedly donned inappropriate outfits during her relationship with Don Jr. Regardless of the occasion, she would always show up in skin-baring and tight-fitting clothes, eventually landing her on President Donald Trump's bad list. And this continued as Don Jr.'s affair with Palm Beach socialite Bettina Anderson made headlines. "Don Jr. has always wanted to look good in his father's eyes," someone close to the first son told People. "Someone like Bettina, who is and has been a model [...] is something [Don knows] would impress him."
Since then, Guilfoyle seems to have moved on from her relationship with Don Jr. — she's even weighed in on his recent engagement to Anderson. During a New York Times interview in January 2026, she spoke positively about her ex-fiancee and expressed no hard feelings towards the couple. "I'm happy for Don," Guilfoyle said. "I wish him, of course, all the best."