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 But as it turns out, Leavitt has favored outdated 'fits since her college days.

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In a throwback Instagram post dating back to 2019, the press secretary can be seen wearing a

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