Kimberly Guilfoyle & Karoline Leavitt Finally Team Up And We Can't Stop Thinking About This One Thing

Even though they're both longtime MAGA devotees, Kimberly Guilfoyle and Karoline Leavitt seem to run in different circles. On September 4, 2025, however, both women had a chance to hang out together at a party for GB News. Leavitt was one of the speakers at the event, and she and Guilfoyle posed for a picture together during the evening's festivities. Standing side by side, the contrast between their styles couldn't have been more different. While Leavitt was emulating Donald Trump with her ill-fitting suit, Guilfoyle traded in her typically overly revealing 'fits for a black pantsuit topped with a leather moto jacket.

Surprisingly, although Guilfoyle is double Leavitt's age, the two women look like they have a 28-year age gap between them. Even accounting for some possible digital retouching before she posted the pic, Guilfoyle's outfit offers a more youthful vibe, compared to the press secretary's bulky cream and greige ensemble. Leavitt's shirt also looked sloppy, and the button-down had a hem that would have looked better tucked in. Guilfoyle's Instagram followers were quick to compliment her style upgrade, too. "Still as beautiful as you were 15 years ago," gushed one poster.

Unfortunately, Leavitt's already had to deal with plenty of age-related flak online, with people theorizing that since her husband, Nicholas Riccio, is 32 years older, their marriage is prematurely aging her. In this case, however, she was probably tired after a long day of work, so an aged-up 'fit was just adding to her problems.

Although some people seem determined to mock Karoline Leavitt's age gap with her husband, Nicholas Riccio, Leavitt has seemed to indicate in interviews that it's actually no big deal. Instead, the reason for the stark contrast between Kimberly Guilfoyle and Leavitt's appearances could come down to different life experiences. When it comes to parenting responsibilities, Guilfoyle's son, Ronan Villency, was born in 2006 and is now a young adult. In contrast, Leavitt's son was born in 2024, so she's only at the beginning of the energy-consuming phase of caring for a toddler.

Then there are professional commitments to consider. Leavitt's role as White House press secretary likely leaves her with a lot on her plate. "You don't have the luxury of getting behind because you'll never catch up," Joe Lockhart, Bill Clinton's former press secretary, informed The Washington Post. "You don't get pure time off." In summer 2025, Leavitt's Instagram reshare about women and stress appeared to be a red-flag confession that she was overly stressed.

Guilfoyle, on the other hand, appears to have more free time in this area, too. Although she's producing new episodes of her podcast on Rumble, her job as ambassador to Greece doesn't seem to have a definite start date. Guilfoyle has made progress, completing her job training in May 2025. She even (unsuccessfully) adopted Leavitt's grandma chic style to receive her ambassador diploma, proving that when they are together, Leavitt and Guilfoyle shouldn't take style inspo from each other.