Kimberly Guilfoyle and Donald Trump Jr have reportedly parted ways, with sources claiming Guilfoyle’s fashion choices played a key role in their split. According to a Trump insider quoted by The Daily Beast, Trump Jr sought a new partner who could better win over his father, Donald Trump, and align with his expectations.
Last week, Trump Jr was spotted holding hands with Palm Beach socialite and former model Bettina Anderson, signaling a new chapter in his love life. Reports by People indicate that Guilfoyle and Trump Jr’s relationship had already been under strain for months, with Anderson entering the picture about six months ago. Sources suggest Trump Jr even took Anderson on a trip to Alaska while still in a relationship with Guilfoyle.
Fashion drama unfolds
A political insider revealed that Trump Jr had voiced dissatisfaction with Guilfoyle’s wardrobe, describing it as “too stiff” and “always professional.” Her signature look—brightly colored, form-fitting dresses paired with high heels — didn’t align with his vision. “Don Jr has been telling people for months that Kim is so uptight and never looks relaxed or casual. The tight dresses need to go, and she has been told that,” the source told People.
Anderson, the Melania counterpart?
Trump Jr’s pursuit of Anderson reportedly stems from her ability to fit into the Waspy, high-society circles of Palm Beach—something that appeals to his desire to impress his father. “Someone like Bettina, who is and has been a model, is exactly the kind of person who would win over Donald Sr,” a source close to the Trump family told The Independent.
A strategic exit for Guilfoyle
Interestingly, Anderson reportedly pushed for Guilfoyle to be sent abroad as her relationship with Trump Jr grew. On Wednesday, Guilfoyle was named US Ambassador to Greece by Donald Trump. Sources said this decision was delayed until after the elections to avoid impacting Donald Trump Sr’s campaign. “They waited for the election to pass but didn’t want the split to hurt Donald in any way,” a political source explained as reported by the People.
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Trump Jr’s public show of support
Despite the swirling rumors, Trump Jr publicly praised Guilfoyle’s appointment on X (formerly Twitter), calling her “a fantastic America First leader.” The couple, who began dating in 2018 following Trump Jr’s divorce from Vanessa Trump, has not commented on the split.
As of now, Trump Jr appears focused on his future with Anderson, while Guilfoyle embraces her new role as ambassador. Whether the rift stemmed from fashion or other factors, one thing is certain—the Trump family drama never fails to captivate.