Karoline Leavitt's Worst Outfits All Have One Thing In Common (& It Makes So Much Sense)

There's something up with Karoline Leavitt's outfits. The youngest White House press secretary in history –- she was 27 when appointed by President Donald Trump -– dresses well beyond her age, and it's unclear why. Part of the problem is the world that she's in. Trump's universe comes with various aesthetics all their own. There's the growing "Mar-A-Lago" face, a term to capture the plastic surgery style that's taken over Trump's inner circle. There's also "Republican hair," which is blonde, heavily styled, and typically features big, bouncy curls, though ultra-sleek hair has worked its way in there, too. 

While the "Mar-A-Lago" face is one aesthetic, there's another style in Trump's circle that's much frumpier. The look is dated and excessively conservative, and this is the category of fashion misfortune that Leavitt has fallen into. The older women try to look younger, while the younger women try to look older, and it's killing Leavitt's style. The press secretary is not alone in this; others in adjacent positions likewise suffer from poor fashion choices. There's Sarah Huckabee Sanders and the outdated trend she was caught wearing. On top of that, Sanders' biggest fashion fails proves that she needs a new stylist. Like the Governor of Arkansas, Leavitt is guilty of repeated fashion fails. For the press secretary, the problem is that she wears drab, frumpy, bland clothes that look uninspiring on someone so young. 

Karoline Leavitt married Nicholas Riccio, a real estate developer, in January 2025. At the time of their wedding, she was 27 while he was 59, marking a 32-year age gap. For Leavitt, the age gap seems to be a non-issue, and she sung Riccio's praises while speaking on The Megyn Kelly Show on February 21, 2025. "[Riccio's] incredible. He is my greatest supporter, he's my best friend and he's my rock," Leavitt told Kelly. "He's built a very successful business himself so now he's fully supportive of me building my success in my career." Leavitt gushed about their son, and expressed her gratitude about the love and support she receives from her husband.

While it's great that Leavitt feels so supported by her husband, our theory is that their age gap is influencing her clothing choices. Her sartorial aesthetic is way older than she is. She wears sombre, muted colors. She wears long skirts and dresses that create a stunted silhouette, and she's frequently in boxy layers that age her. She loves bouclé sets and big blazers with long slacks. She dresses like a woman in her husband's age bracket, not like a woman in her late 20s. Our theory is that her husband's sensibilities are influencing her fashion taste. Maybe once Leavitt gets more comfortable at her job – she only assumed the office on January 20, 2025 — she'll experiment with different styles and wear more age-appropriate clothing.