Kimberly Guilfoyle’s Fashion Choices Sparked Split From Don Jr.
The younger Trump was reportedly searching for someone whose style would impress his father—he has apparently found that in socialite Bettina Anderson.

Illustration by Eric Faison/The Daily Beast/Getty Images
Kimberly Guilfoyle’s style choices drove fiancé Donald Trump Jr. to seek a new girlfriend who would better “impress” his father, according to a Trump insider.
Don Jr. was spotted holding hands this week with Palm Beach socialite Bettina Anderson.
Trump Jr. and Anderson reportedly began dating six months ago, while Guilfoyle “looked the other way,” according to People. Guilfoyle, 55, was named ambassador to Greece by Donald Trump on Wednesday, and People reported that it was Anderson who pushed for her to be shipped off.
In the latest twist, a source close to the Trump family has told People that Trump Jr. has pursued Anderson, 38, because he thought she could be his Melania Trump equivalent—and win over his father.

Anderson and Trump Jr. were spotted holding hands in public this week.
John Parra/Getty Images
“Don Jr. has always wanted to look good in his father’s eyes,” the source told People. “Someone like Bettina, who is and has been a model, and is in Waspy circles of Palm Beach is something that would impress him.”
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Apparently, a key sticking point in the relationship were Trump Jr.’s qualms with Guilfoyle’s style—largely an assortment of brightly colored, form-fitting dresses.
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“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,” the source said. “The tight dresses need to go and she has been told that.”

Guilfoyle’s style is marked by bright, close-fitting dresses.
Chip Somodevilla/Getty Images
While none of the involved parties have yet commented on the relationship developments, Guilfoyle has reportedly been on the chopping block since well before the election, but the family waited to make any movements on the split to ensure it would not have any influence on Trump Sr.’s campaign, according to People.
Despite the rumors, Trump Jr. was effusive on social media when his father announced that Guilfoyle, a former Fox News host, would become an ambassador.
“I am so proud of Kimberly,” Trump Jr. wrote on X of Guilfoyle, whom he began dating in 2018 after splitting from his then-wife Vanessa Trump. “She loves America and she always has wanted to serve the country as an Ambassador. She will be an amazing leader for America First.”
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