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Within the political sphere surrounding Donald Trump, Kimberly Guilfoyle’s fashion choices often raised eyebrows, sparking questions about her sense of judgment. It wasn’t just observers who took notice; her bold wardrobe and personality may have influenced the trajectory of her diplomatic ambitions following her public breakup with Donald Trump Jr. Reports suggest that Guilfoyle aspired to represent the U.S. at the Vatican, although she was instead offered Greece.
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According to insiders, the notion of Guilfoyle serving as ambassador to the Holy See was quickly dismissed. “It was unexpected, and there was never any serious consideration for her to be appointed to the Vatican,” a source remarked in an October 2025 interview with the Daily Mail. Her assertive demeanor was seen as too unconventional for the role, leading to a consensus on appointing her to Greece instead.
However, those close to Guilfoyle refuted claims that she sought a Vatican position. “She’s thrilled to be named the first female ambassador to Greece,” an insider stated. When her appointment was officially announced in late 2024, speculation arose that the Trump family was distancing her from Don Jr. and his new partner, Bettina Anderson. Yet, confidants insisted that Guilfoyle was genuinely pleased with her new diplomatic role. “There’s no need to feel sorry for her,” a source assured People, despite long-standing tensions over her public image.
Guilfoyle’s fashion choices were not without critics, and Donald Trump Jr. reportedly was among them. He allegedly urged his then-fiancée to adopt a more understated style. “Don Jr. has mentioned for months that Kim’s attire was always so formal and never relaxed,” a source shared with People in December 2024. “He suggested she tone down her tight dresses.”
Despite these critiques, Guilfoyle maintained her distinctive style throughout their six-year relationship. However, just before their split, she appeared to pivot towards a more casual look, possibly as a last-ditch effort to mend the relationship. “Kim isn’t happy about the breakup,” a source revealed to Page Six. In the weeks leading up to the announcement, she was seen opting for more relaxed outfits, seemingly signaling a change in approach.
Donald Trump Jr. reportedly disliked Kimberly Guilfoyle’s fashion
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Kimberly Guilfoyle’s fashion sense had many detractors, and Donald Trump Jr. was apparently one of them. He is even said to have asked his then-fiancée to tone it down some. “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, and never looks relaxed or casual,” a source told People in December 2024. “The tight dresses need to go and she has been told that.”
Given that Guilfoyle remained steadfast in her style throughout their six years together, it’s easy to presume she didn’t take his advice — or at least not until the very end. Guilfoyle had a notable style change before the bombshell split from Don Jr., perhaps suggesting a last-minute attempt to fix the relationship. “Kim is not happy about it,” a source told Page Six. “She didn’t want it to end.” A month before they announced their breakup, she ditched her low-cut dresses in favor of more casual outfits on separate outings.
These social media posts added fuel to the rumors that Guilfoyle’s inappropriate outfits landed her on Donald Trump’s bad list. And Don Jr. seemingly really wanted to find a partner who pleased his father. “Don Jr. has always wanted to look good in his father’s eyes. Someone like Bettina [Anderson], who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him,” the insider told People.
