The Tamesis
What makes someone like Caroline Bessette Kennedy an enduring fashion icon? On the one hand, there’s a collection of clothing that people still can’t stop thinking about (and copying) decades later. CBK became a major tabloid focus in the 1990s due to her relationship with John F. Kennedy Jr., and her wardrobe of smart coats, stylish shoes and tailored jeans has been featured on mood boards ever since.
One of her well-documented wardrobe mainstay pieces? Her classic denim. Bessette-Kennedy’s bootcut jeans are so famous that Ryan Murphy’s new collection’s clothing department Love Story: John F. Kennedy Jr. and Caroline Bassett No effort was spared to recreate them. “We put Caroline in some Levi’s jeans,” star Sarah Pidgeon, who plays CBK on the show, recently told Us Fashion.
In fact, CBK’s go-to style—Levi’s 517s—is surprisingly affordable and can still be purchased today. The brand first introduced the bootcut silhouette in 1969, and the shape has remained popular ever since as the flared leg works so well with boots or heels. (CBK is one of them, wearing them both ways.)
Photo: Getty Images
While I’ve long been inspired by CBK’s smart, timeless sense of style, it turns out I’ve also been attracted to the same jeans for years. I remember buying my first 517 in high school in the 2000s, when I had a fascination with 1970s fashion. The shape of bell bottoms is reminiscent of bell bottoms, but subtler and more modern. Later, as I became an adult, I realized how wonderful they looked as an everyday pairing with heeled boots, and how sophisticated and classy the combination could feel without much effort.
But that’s the beauty of CBK’s fashion: She can take the most humble or plain pieces and instantly make them feel (and look) like a million bucks. So while I wasn’t directly influenced by CBK to invest in 517, I realize she was completely ahead of her time. Even in 2026, they remain the most secretive and chic jeans in fashion.
