Carolyn Bessette Kennedy’s favorite jeans are still available to buy — and under $75

When two unforgettable fashion icons were joined at the hip.

Carolyn Bessette Kennedy’s elegant style was the essence of 90’s minimalism — a clear shift from the prior decade’s maximalist fashion. And yet, that timeless aesthetic has never been more sought after today; think quiet luxury before it was a trend.

Case in point: CBK loved her retro bootcut Levi’s 517 jeans, a leg-lengthening style she paired with boots and heels alike for a casually polished look. The former Calvin Klein exec added belted coats and a tee, turtleneck or crisp white button-down for infinite spins on the American classic, a sartorial embodiment of her low-maintenance style.

While it first debuted in 1969, Levi’s still makes the exact cut, and it can be shopped for $75 or less. (Levi’s is offering 30% off purchases over $125, to boot.)

Levi’s 517 Bootcut Jeans in Medium Stonewash

Yes, the Levi’s 517 is a men’s style; however, if you’re old enough to remember, that was the original way to wear a “boyfriend” jean. The lack of a cinched waist creates an effortlessly cool drape on the hips, but can also be belted as desired.

Carolyn Besette Kennedy in New York City in 1997. ZUMAPRESS.com

CBK favored medium and darker rinses — perfect for her oft-neutral colored wardrobe — whether strolling the streets of downtown Manhattan or enjoying weekends in the Hamptons.

Just add an L.L. Bean Boat and Tote — and perhaps a Cartier Tank Française watch, if you really want to channel the vibe.

Levi’s 517 Bootcut Jeans – Medium Wash

Available in 100% cotton and stretch blends, the 517 has a bit of a higher waist and a subtle bootcut. For sizing, consider that men’s cuts have a smaller waist-to-hip ratio, so check measurements to find yours.

Otherwise, a rule of thumb is to add 21-22 to your normal size, e.g., a size 8 will be a 29 or 30.

Levi’s 517 Bootcut Jeans – Dark Wash

With the popularity of the new Ryan Murphy series “Love Story: John F. Kennedy Jr. & Carolyn Bessette,” expect the late style icon to influence fashion trends this year, a testament to her enduring grace.

Bessette Kennedy and John F. Kennedy Jr. in NYC in 1998. Lawrence Schwartzwald

The way she wore her jeans was so iconic that it was critical to the show’s wardrobe department to nail it, with star Sarah Pidgeon, who plays Bessette Kennedy, telling Vogue, “We fitted some Levi’s so that they looked exactly how they fit Carolyn.” 

No matter how you wear it, there’s a lot to love about things that never go out of style.

Why Trust Page Six Style Shopping

This article was written by Erica Radol, Page Six Commerce Reporter. From identifying the top anti-aging skincare secrets the stars trust to dishing on the latest fashion collabs to finding a great deal on all of the above, Erica has a knack for reporting on – and even testing – Hollywood’s bestselling fashion and beauty products. Before joining Page Six in 2025, she wrote about entertainment, lifestyle and shopping trends for Us Weekly, The Daily Beast, Entertainment Tonight, Well+Good and Hearst.