Kimberly Guilfoyle's Spicy Style Reportedly Made Her Dream Trump Admin Job A No-Go

Kimberly Guilfoyle reportedly wanted to be the U.S. Ambassador to the Vatican but had to settle for being the U.S. Ambassador to Greece. One doesn't need to be Catholic to realize why making the former prosecutor the go-to person to the Vatican would have been a horrible idea.

For starters, the mother of one constantly seems to dress like she's either coming from or about to hit up the club. The outfits she wears to special events and for work tend to have large cutouts that show off the girls, are form-fitting, and/or include tacky bows. None of those screams "Vatican appropriate." Clearly, President Donald Trump felt the same way, because he reportedly put the kibosh on Guilfoyle's dream gig. According to a source at the Daily Mail, Trump said Guilfoyle's Vatican aspiration was "a non–starter."

The outlet noted that although Guilfoyle is Catholic, her reputation pretty much ruined her chances on the spot. "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," claimed another source. Guilfoyle is also not afraid to speak her mind, no matter what may come out of her mouth. This lack of decorum also worked against her favor for the job.

It's not like Kimberly Guilfoyle's clothing choices have been a recent issue for the Trump administration. When she was dating and later engaged to Donald Trump Jr., the first son criticized her style — which she never let faze her. Back in December 2024, a source told People that Don Jr. was low-key seeing socialite Bettina Anderson, while he was still with Guilfoyle, and thought she fit into his family much better than Guilfoyle did. "Don Jr. has always wanted to look good in his father's eyes." Ditching your fiancée because Daddy won't give you approval seems like a humiliating reason to dump someone you supposedly love.

Nevertheless, Guilfoyle is gonna Guilfoyle, and she kept her outfit spicy at her farewell bash in October 2025, before she left for her job in Greece. Meanwhile, Don Jr. is still craving his father's blessing.

Guilfoyle's Greece job, however, didn't happen without some serious nudging. Sources told the Daily Mail that it was Sergio Gor, the U.S. Ambassador to India, and someone close with both Guilfoyle and Don Jr., who helped get her on the short list for the job. Sounds like cronyism at its finest.