There was a time, not so long ago, when it was all about slouchy silhouettes and puddling hems. Street-stylers would wear jeans—and still do, actually—that completely swallowed their shoes (we all remember the summer of ’24, when everyone had a little triangle of boot poking out of their jeans). Now, though? A vibe shift. Not only have straight-leg jeans emerged as a dominant denim trend, but the cropped sort are right up there, too–I’m talking about ankle grazers, the type loved by ’90s celebs from Carolyn Bessette-Kennedy to Cindy Crawfor to Julia Roberts.

It should surprise no one that ’90s cropped jeans are enjoying a moment in the sun. We’ve witnessed a kind of mass hysteria-like event following the release of Love Story, with everyone dressing like CBK, and she famously wore cropped jeans regularly (the Levi’s 517s specifically, which have a bootcut silhouette and a hem that hits just above the ankle). Cropped jeans have also been a fixture on recent runways–Celine’s spring/summer 2026 show saw models sent down the catwalk in cropped jeans that showed off ankle socks and jazz derbies.

Even so, cropped jeans aren’t always easy to get right. “It can be tricky to find the perfect hemline, that hits the ankle just so and ensures the proportions are balanced,” fashion editor Mai Morsch wrote previously. “A length that’s too high can look unintentional, but when the jeans aren’t cropped enough they look like they don’t fit properly.” I like to go for Levi’s, personally, as the fits never fail me–but as with any jeans, it’s worth getting well-acquainted with your exact measurements before purchasing.

The bonus? These jeans will actually show off your shoes.

Re/Done

cropped wide-leg jeans