Carolyn Bessette Kennedy Swore By Bootcut Jeans for Casual Polish

2 min read

There’s a lot to be said about Carolyn Bessette Kennedy—especially when it comes to fashion. Studying her take on personal style is a masterclass in ’90s style and executing timeless elegance. Her effortless approach to fashion no doubt had roots in her work as a publicist for Calvin Klein, but it was also her more approachable choices—like her $17 signature scent—that made her especially alluring (and somewhat relatable) to onlookers across the country.

One can look through Bessette Kennedy’s most iconic ’90s outfits and their individual pieces—the sleek camel brown pencil skirt, the leopard print coat, and, of course, the Narcisco Rodriguez slip dress wedding gown—and start to build a capsule wardrobe for any season. Of course after spending the better portion of my downtime devouring Ryan Murphy’s Love Story: John F. Kennedy Jr. and Carolyn Bessette, my eyes aren’t going for the work-appropriate sweaters or even her cocktail-ready tube dresses. Instead, I’m captivated by the wardrobe staple she seemed to wear nearly all the time: bootcut jeans.

After careful research, I’ve come to discover that Bessette Kennedy’s ride-or-die style of choice was the Levi’s 517—a classic high-rise bootcut silhouette that slimmed the leg while leaving the perfect amount of flare for those ’90s boots. Levi’s no longer carries a women’s fit for the 517, but the closest option you’ll find is the Wedgie Bootcut.

As a denim lover myself, I’ve gone back and forth between more fitted styles like slim bootcuts and ultra-baggy, almost sweatpant-like jeans. However, seeing just how chic a pair of jeans can be, as demonstrated by the ’90s minimalism fashion icon, I’m officially declaring 2026 the year bootcut jeans make their return to the spotlight. Style them with classic boots or a pair of chic loafers (as seen on Bessette Kennedy here) or even a set of heels if you want to dress them up a touch. And given how well her style holds up decades later, I guarantee this is one denim trend that will age well in your closet.