Kendall Jenner Got a Schoolgirl Wardrobe to Match Her Bob

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There was a moment during the spring 2025 collections when Kendall Jenner–the raven-haired embodiment of a ’90s socialite in straight-legged jeans and loafers–all but disappeared. The baseball caps and outsized suede jackets that had for years distinguished the model’s pap walks were all of a sudden replaced with an old-world vision of a dignified blonde in vintage John Galliano suits and shin-length Mugler skirts styled with Hermès briefcases.

“Kendall knew her hair would be blonde and we wanted to style around it,” Jenner’s stylist Dani Michelle said, adding that her client was inspired by “classic, elegant tailoring.” If a trip to the colorist Jenna Perry gave rise to all that ladylike suiting during Paris Fashion Week, then her latest switch-up–a gamine bob in her natural shade of brunette–has once again dovetailed with a subtle, but significant style, shift. The model was photographed strolling through Los Angeles yesterday afternoon in a charcoal vest tugged over a pinstripe shirt with a Reformation miniskirt and a sensible handbag.

She looked like the head girl of a private school in Calabasas–which is, of course, not how Jenner dressed when she attended the expensive Sierra Canyon School before switching to an at-home education program in 2012. Jenner’s teenage years were a cauldron of leather skinnies and perspex heels, slogan sweaters and snoods, knitted waistcoats and flower crowns. “Some days I’m into this,” she said at the time. “And other days I’m into that.” Hers is a mercurial relationship with fashion, as fluid and changeable as the next haircut.

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Shop Jenner’s schoolgirl look, below.