Kimberly Guilfoyle's Inappropriate Persona Reportedly Lost Her More Than Just Don Jr.

During her time in Donald Trump's inner circle, Kimberly Guilfoyle donned some inappropriate outfits that left us questioning her judgment. We weren't the only ones. Her wardrobe choices and general boldness may even have played a role in the direction her diplomatic career went after Guilfoyle's messy breakup from Donald Trump Jr. As it turns out, she reportedly wanted the ambassadorship of the Vatican, not Greece.

However, the president and his advisers thought she was a bit too much to represent the U.S. in the Holy See. "It came out of left field. There was no way they were going to give her the Vatican. It wouldn't be a fit, for many reasons. She must have known that," a source told the Daily Mail in October 2025. Others noted that the thought of having such a fiery personality in the headquarters of the Roman Catholic Church was deemed "unconventional, if not controversial." Amid the negotiations, they landed on Greece as a compromise.

However, sources close to Guilfoyle denied she ever pursued the Vatican. "[She is] very excited to be the first female ambassador to Greece," an insider said. When her new role was announced in late 2024, the public speculated that the Trump family just wanted to ship her off as far as possible from Don Jr. and his new girlfriend, Bettina Anderson. But insiders guaranteed that Guilfoyle was ecstatic. "Do not feel sorry for her, or think she's being pushed off to the side," a source told People. However, the Trumps had reportedly had issues with her inappropriate persona for some time. 

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.