Kimberly Guilfoyle Takes Fashion Inspo From Karoline Leavitt In New Pics

By Shana Aborn
Kimberly Guilfoyle smiling widely in a blue blouse with a big bow Giannis Papanikos/Shutterstock

Having given her chilly well wishes to former fiancé Donald Trump Jr. on his engagement, Kimberly Guilfoyle is focusing on her new life as the U.S. ambassador to Greece. The former Fox News host's days are typically filled with meetings with various Greek officials and fellow diplomats to further cement the relationship between the two nations. As such, she has reverted back to the professional style she donned as a practicing attorney. Guilfoyle is known for wearing inappropriate outfits both to social and work occasions, so it's a relief to see her representing the United States in a less wince-worthy fashion. 

Still, there's a happy (and wide!) medium between provocative and dowdy, and sadly the former Fox News host doesn't seem to have found it quite yet. She may be sidelining her low-cut minidresses for the sake of propriety, but Guilfoyle is now substituting pieces that rival even Karoline Leavitt's outfits, who frequently dresses much older than she is. Like the White House press secretary, Guilfoyle has turned to unflattering styles and fabrics that demand attention — all of it negative. Take, for instance, this 'fit, which the ambassador chose for her meeting with Federal Reserve Governor Stephen Miran. 

No one could accuse her of indecent exposure; the neckline is as modest as they come. Yet the boxy cut and odd fringed scarf detail were grandmacore at best, and the cotton candy-pink shade looked frivolous when contrasted with the conservative suits of her colleagues. The Trump staffer would have been better off going with one of the pantsuits she's been wearing as of late. Guilfoyle almost always pairs them with satin bow-tie blouses that come straight from the corporate "Working Girl" style of the 1980s. The look still sticks out from the rest, but at least it's businesslike.

Guilfoyle and Leavitt convey power through plackets

Split image of Kimberly Guilfoyle and Karoline Leavitt wearing similarly dowdy dresses while smiling Andrew Harnik/Getty & kimberlyguilfoyle/Instagram

Kimberly Guilfoyle did some serious twinning with Karoline Leavitt during her meetings with Stephen Miran and Greek Prime Minister Kyriakos Spirotakis, in January 2025. She donned a white wool jacket dress with jeweled button details, which bore more than a passing resemblance to the blinged-up schoolgirl style Karoline Leavitt has worn on numerous occasions. Both outfits also featured a number of front pocket plackets, which are meant to convey a sense of importance. Needing pockets means that you have valuable items to carry around, which wasn't always the case for women in centuries past. In this case, though, the pockets are merely decorative, which contradicts the girl-power message. 

In her spare time, the U.S. ambassador to Greece reverts back to the glam-wear that supposedly was part of the reason Donald Trump Jr. broke up with Guilfoyle (rumor has it the Trumps were a bit embarrassed by her overtly sexy dresses and wondered what kind of image she might present to the public as an in-law.) A whirl of social events upon her arrival in Greece found the former Fox News host partying heartily in revealing gowns. 

Then, in December 2025, Guilfoyle's Christmas photo showed Don Jr. exactly what he missed out on; the form-fitting gold and silver gown was both stunning and age-defying. If the Trump staffer can somehow find a way to carry that agelessness over into her business-wear, she could become one of the most fashionable women in the whole administration. Honestly, though, we'd be happy for now just to see her ditch the plackets and rhinestones.

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