College Pic Of Karoline Leavitt Hints Her Obsession With Grandma Clothes Started Young
To many pundits and fashionistas, Karoline Leavitt's wardrobe choices are utterly baffling. She doesn't dress like her Gen Z peers; on the contrary, Leavitt has a tendency to dress way older than she is. She favors bouclé and pantsuits, but she also has a habit of picking clothes that seem way too big for her. In fact, Leavitt's October 2025 frumpy fashion fail looked like it was borrowed from her husband's closet. One could argue that the press secretary is purposely trying not to dress her age in an attempt to downplay the 32-year age gap she has with her husband, Nicholas Riccio. But as it turns out, Leavitt has favored outdated 'fits since her college days.
In a throwback Instagram post dating back to 2019, the press secretary can be seen wearing a loose-fitting shirt featuring what is arguably a very grandma-esque pattern as she poses for a farewell photo with a fellow student after finishing their final broadcast for the Saint Anselm Broadcasting club. This was the same year Leavitt graduated college, and all the signs of her future fashion sense were on full display. Perhaps the press secretary is somewhat of an old soul, but there's no arguing that many of her 'fits look like she raided the late Queen Elizabeth II's closet.
Leavitt's designer has given more insight into her style
While Karoline Leavitt's grandma cardigans have a tendency to make her look older than her husband, she does, thankfully, don an age-appropriate suit every now and then. This is all thanks to Boston-based designer Christopher Cuozzo, who has designed multiple suits for the White House press secretary. When he spoke to WWD in May 2025, he called Leavitt's style "very American, classy, sophisticated and elegant," but added that she mostly gives him free reign when it comes to designing her suits. "She'll look to me for colors and ideas ... She will say, 'Yes. No.' but she leaves the design to me — lapels, buttons, and linings," he said.
In another interview with Business Insider that same month, the Boston designer said that Leavitt opts for classic and timeless styles, adding, "I don't envision her wanting to do some very loud plaid suit that's a bunch of different colors." Given some of the press secretary's questionable fashion choices during her tenure that's, um, debatable. Cuozzo admitted that he was surprised when Leavitt asked him to design her a bright red suit, but conceded that she could pull off the look because she's still young.
It should come as no surprise that Cuozzo's clothes don't come cheap. His women's suits start at an eye-watering $1,495. When asked how much Leavitt has spent on her tailored suits in total, Cuozzo declined to answer. "I'm going to keep that between her and me," he told Business Insider.