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Carolyn Bessette-Kennedy is more than just a fashion icon. Her life, her iconic romance with John F. Kennedy Jr., and her minimalist style continue to inspire in 2025. Today, this enduring influence is at the heart of Ryan Murphy’s new series, American Love Story, in which young actress Sarah Pidgeon is challenged with stepping into the shoes of a woman who became synonymous with the idea quiet luxury. “Her style wasn’t opulent, but it was luxurious,” author of CBK: A Life in Fashion Sunita Kumar Nair, tells Vogue. “The fact that she only had a few pieces shows how modern she was. Her look said, ‘Here I am, impeccably dressed in a masculine silhouette, yet retaining my femininity.’ There were no frills, prints or excessive accessories, nor was it an ostensible power dressing.”
When we look back at Carolyn Bessette-Kennedy’s style moments from the 1990s, her rise to the role of advertising director at Calvin Klein makes perfect sense. With her innate confidence, she built her look around simple essentials, all of which had one thing in common: they were perfectly cut. Whether she was in silky slip dress, a button-down and maxi skirt, or T-shirt and jeans, she always wore it with a New Yorker’s sense of natural ease.
It’s no secret that Bessette-Kennedy was a big fan of Levi’s; it’s rumored that her favorite was the brand’s 517 model, featuring a bootcut flare that was very popular in the 1970s. On vacation in Martha’s Vineyard, Massachusetts, or on the streets of Manhattan, it was not uncommon to see her wearing this classic denim style, as well as other flared jeans.
Nearly 30 years later, bootcut jeans are as popular than ever. Seen on Jennifer Lopez, Kate Moss, and more recently on Bella Hadid, the silhouette saw a major search spike after Kendrick Lamar stepped onto the Super Bowl stage in January 2025 in bootcut Celines that captivated audiences worldwide. Almost overnight, everyone wanted a pair.
Discover an edit of bootcut jeans that are perfect for fall, inspired by Carolyn Bessette-Kennedy’s timeless style.
