The Trend We Wish Karoline Leavitt Wore More Often

There's more than one way to be divisive, and Karoline Leavitt seems determined to try them all. The Trump White House staffer and self-styled Gen-Z firebrand has built her political persona on blind loyalty to her boss and a remarkably short fuse when it comes to journalists. But, like many figures forged in the furnace of the 24-hour news cycle, her visual presentation has become part of the brand — and it's not always been flattering. Leavitt's spiciest outfits clash with her press secretary persona, whilst her frumpiest work outfits seem pulled from a congressional costume closet.

Despite the precedent she sets with her wardrobe now, there was a brief, almost blink-and-you-miss-it moment of style redemption. Believe it or not, she surfaced in a completely unexpected, genuinely cute outfit in an Instagram photo dump from September 2023. The look featured a fluid chambray denim shirt tucked into high-waisted flared jeans (which you can style for any occasion), paired with white strappy heels and a baby blue shoulder bag.

If Karoline Leavitt outfits have often totally missed the mark, at least this one showed a little direction. The look appeared during an outing with her girlfriends (who may have gently steered her away from the beltway blazer uniform and towards something more fun). It hinted at a version of Leavitt who, arguably unlike the one we see before us today, understands how great style is good for optics. For once, she finally looked like someone who'd found her footing — sartorially speaking, at least. It was a rare case of her fashion winning the popular vote.

Karoline Leavitt shot to political prominence as the youngest-ever White House press secretary — a title she wears with pride. Born in 1997, she has relied heavily on her generational credentials to signal a youthful reboot of conservative politics. "There's a real lack of young conservative voices that are reaching out to my generation," she told the Daily Mail. "That made me want to get involved." But, for someone so eager to represent the next era, her aesthetic choices rarely reflect that same implied forward-facing instinct.

This generational disconnect is difficult to ignore, especially when set against her peers. A YouGov poll found that Gen Z are the most mindfully, intentionally fashionable demographic, with nearly half saying they're more fashionable than most people. Highly attuned to the semiotics of style, they borrow liberally from the past, flipping uncool into cool. Leavitt, by contrast, is stubbornly conservative in more ways than one, dressing in ways that show little generational fluency.

The contrast was particularly glaring in 2025, when she appeared in an interview with Instagram influencer Kate Mackz. For the occasion, the press secretary wore an ensemble in butter yellow — the on-trend color of 2025. But the result curdled on impact. Sadly, Leavitt butchered the butter yellow color trend with her sloppy outfit. Her crinkled sleeveless pantsuit came in an awkward fit that aged her. Though the color choice implied trend awareness, the execution suggested a studied detachment from what actually makes fashion feel current. Asked in the full interview (via YouTube) what she would tell her past self, Leavitt answered, "just keep going. Just keep working." We suggest she also keep a stylist on speed dial.