Kendall Jenner's Milan Fashion Week Arrival Did It—I'm Sold on 2026's Most Elegant Flats Trend
Thanks to her, I'm not too late to the party.
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Do I know Kendall Jenner's Milan Fashion Week schedule? No, the supermodel keeps that under lock and key. I'm not completely out of the loop, though. I do know which new ballet flats trend will take her from show to show this season. Drum roll, please: It's the high-vamp style Jenner helped boost to It-shoe status earlier this year.
Technically, Milan Fashion Week started bright and early on February 24. In my book, it couldn't fully begin until at least one Jenner set foot in Italy. The oldest sister was photographed outside her five-star hotel, wearing what could be her most relaxed look of the week. It seems Jenner curated her selects based on what would complement her favorite Spring 2026 shoe trend the best.
She stacked a black, long-sleeve crewneck on top of a white T-shirt in '90s fashion. Then, Jenner's Carolyn Bessette-Kennedy-coded minimalism continued with a charcoal gray skirt. Jenner must've known I wanted her tried-and-true flats trend front and center, rather than hidden under travel pants.
Kendall Jenner arrived at Milan Fashion Week wearing the high-vamp flats trend, of course.
To make up for yesterday's Instagram Stories mirror pic—which made her The Row Stella Python Slippers extra tricky to ID—Jenner separated her skirt's hem and shoes by a good three feet. That way, I could appreciate and copy every element of the Jenner-led high-vamp flats trend.
Similar to her beloved The Row Eve Slippers, each curved, black toebox featured "a glove-like construction and an extended upper," to quote Marie Claire's fashion editor Lauren Tappan. The vamps stretched as far down her feet as regular loafers, minus the suspended tongues. After zooming in, I noticed another element set these high-vamp flats apart from their The Row predecessors. A glossy pinstriped (or dare I say, croc-embossed?) sheen appeared to decorate every visible exterior.
You (and I) heard it here, folks: Jenner plans to broaden the high-vamp flats trend far beyond her original black leather pair. The day prior, she debuted a brand-new color and texture with The Row's sold-out snakeskin slippers in beige. Like her Milan Fashion Week calendar, Jenner's next high-vamp flats are impossible to predict. The good news is, her shoe rack is nowhere near full.
See how her high-vamp flats aren't perfectly patent? They're almost croc-embossed.
The Jenner-led high-vamps trend is no stranger to Milan Fashion Week. Similar styles became a staple on the Spring 2026 street style scene last September. Typical ballet flats cover just the wearer's toes, but as the week went on, vamps stretched further and further toward the ankles.
Jenner hasn't attended (or walked) a runway show in Milan since Bottega Veneta's Spring 2025 show in Sept. 2024. However, it seems she kept tabs on flats-wearing insiders last season, waiting for the moment she could follow suit.
A MFW guest brought the soon-to-be trend from front row to front row.
Mesh high-vamp versions even appeared on the streets of Milan.
This showgoer gave Mary Janes the high-vamp treatment.
Knowing Jenner, she and her signature Spring 2026 shoe trend have RSVP'd "yes" to a runway show or two this week. Don't be surprised if the flats join her in the front row—or better yet, on an actual Milan Fashion Week runway. In the meantime, my edit of elegant, high-vamp flats below. I already have a style (more like two) in my cart. Do you?
Shop the High-Vamp Flats Trend Inspired by Kendall Jenner
