School Season Too Literally In Outdated Uniform ‘Fits

During her tenure behind the podium, White House press secretary Karoline Leavitt has had a hard time finding clothes that properly fit both her frame and her sense of style. While in the past, Leavitt has dressed more like a school teacher, as the summer comes to a close it seems she’s switched gears and is now reaching for pieces that look more like a school girl stuck in the 1950s. During a press briefing on August 14, 2025, Leavitt boasted a youthful glow courtesy of her blonde hair, but once again paired her makeup with an outfit fit from a bygone era.

Leavitt has a penchant for dressing much older than she really is, but this new trend of wearing tweed pieces with large, structured collars feels incredibly reminiscent of post-war school uniforms. There’s even this matching set Leavitt boasted about on Instagram, complete with plaid pleats and large buttons — it really does come across as a uniform fit from the 50s. There’s been some indication that Leavitt’s MAGA makeover has ruined her sense of personal style, and the more the youngster tries to lean into past fashion, the more incongruent and uncanny it becomes to take her all in. With such a modern face, and such outdated sensibilities, Leavitt is still struggling to find a consistent way to present herself.

Karoline Leavitt keeps toying with her vintage style

Karoline Leavitt has undergone a wild transformation on her journey to becoming the youngest White House press secretary in history. However, within this shift, Leavitt has found it difficult to find a style that effectively communicates her position. Leavitt seems to constantly reach for outfits that miss the mark, subtly sending the message that she might not have been prepared for this job at such a young age.

Of course, wearing dresses inspired by the 1950s does suggest that Leavitt wants to be perceived as an adult, even if it means wearing fashions sported on “Leave It to Beaver.” Dressing this way does help communicate that her values are closely intertwined with an era associated with the nuclear family and conservatism, but doing so with possible lip fillers makes Leavitt’s face feel at odds with her fashion.

There are plenty of ways Leavitt could casually update these looks without totally eschewing her desire for a different time. Softening the fabrics she reaches for, opting for more high-waisted, wide-leg trousers, and recruiting a tailor to make the clothes fit her small frame are all within Leavitt’s grasp, which makes it feel as if her insistence on dressing for a nursing home is a personal choice. Although, wearing heavy cotton, wool, or even tweed during a Washington, D.C. summer still feels ill-advised.