Kimberly Guilfoyle's Inappropriate Outfits Reportedly Landed Her On Trump's Bad List

Donald Trump Jr. and Kimberly Guilfoyle had apparently been on the outs for quite some time before reportedly breaking up, and one of the reasons was the way Guilfoyle dressed. Days after Donald Jr. packed on the PDA with rumored girlfriend Bettina Anderson in Palm Beach for her birthday weekend, a report surfaced with details as to why he chose to date the model. Apparently, it partially had to do with appeasing Donald Trump. "Don Jr. has always wanted to look good in his father's eyes. Someone like Bettina, who is and has been a model ... is something that would impress him," an insider told People on December 12. Not only did Donnie want to appease his pops, but he was reportedly fed up with Guilfoyle, who "never looks relaxed or casual," as her default garb was form-fitting dresses regardless of the occasion. "The tight dresses need to go and she has been told that," the source added.

When news first broke about Junior and Anderson in September, Guilfoyle attempted to squash break-up rumors with her fiancé by posting a PDA-filled Instagram carousel of their joint visit to Kentucky. While Donald Jr. kept it casual in an untucked button-down and blue jeans, Guilfoyle rocked a low-cut red dress. A month later, Guilfoyle opted for an inappropriate mini-dress while out on the campaign trail in Michigan.

Don's frustration with Guilfoyle, and her gaudy dresses, had purportedly been boiling over long before reports about his romance with Anderson started circulating. "Don and Kimberly haven't been getting along over the past year," a source told Page Six on December 11. The insider added that the engaged couple had called it quits. "Kim is not happy about it. She didn't want it to end," they said. More details about their break up emerged as well.

According to another insider, Donald Trump Jr. and Kimberly Guilfoyle had been broken up for quite some time before the photos of him and Bettina Anderson made the rounds. "Don and Kimberly broke up before the election and started to divide assets around the end of September," an insider told Us Weekly on December 11. The two had kept the break hush-hush so as not to "detract from" Donald Trump's presidential campaign. That source also had intel about Junior's new relationship. Even though Donald Jr. and Anderson have a sizable age gap, he is reportedly "smitten" with the model. The reported split from Guilfoyle seems to be for keeps, as another source told People that Donnie had been dating Anderson for "about six months" and "even took her on a trip to Alaska."

Not only has Donald Jr. moved on with Anderson, but he's putting some distance between himself and his ex — Donald announced that he's shipping Guilfoyle off to Greece to act as an ambassador for the United States abroad. "I am so proud of Kimberly. She loves America and she always has wanted to serve the country as an Ambassador," Donald Jr. wrote on X, formerly Twitter, after his dad announced Guilfoyle's new appointment on December 10. A couple of days later, a source who spoke to People said that Junior's new girlfriend influenced that decision. Anderson apparently wanted Guilfoyle "out of the area" as her relationship with Don intensified.

Months before the position was announced, Guilfoyle had traveled to Europe with Donnie as part of the elder Trump's presidential campaign. Unsurprisingly, Guilfoyle sported her typical inappropriate dresses while posing for pictures alongside Donald Jr.