Carolyn Bessette Kennedy's '90s Bootcut Jeans Are Back in Style

The iconic Levi's 517 fit is no longer available, but the brand's Wedgie Bootcut Jeans offer a similar look.

Mar. 13, 2026 at 8:53pm

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Carolyn Bessette Kennedy's '90s style, including her go-to Levi's 517 bootcut jeans, is making a comeback. Though the original pair is hard to find, Levi's Wedgie Bootcut Jeans offer a similar silhouette that is versatile and elevated. Fashion experts explain how the bootcut jean, born out of utility rather than trend, can transition from casual to sophisticated.

Why it matters

Bessette Kennedy's minimalist, understated style has continued to influence fashion decades later. The revival of the bootcut jean, a practical yet polished look, shows how certain timeless silhouettes rarely go out of style when paired with the right pieces.

The details

The Levi's 517, commonly known as the 'Saddleman jeans', was designed to accommodate western boots, with a higher rise in the front and back to keep the wearer's backside covered while seated on a saddle. Though the original 517 is no longer available, Levi's Wedgie Bootcut Jeans offer a similar cut that can transition from casual to elevated. Fashion experts note the bootcut silhouette, unlike a true flare, has a subtle wider opening at the base of the leg to fit over boots, creating a feminine and 'almost sexy' look.

  • Carolyn Bessette Kennedy's iconic '90s style continues to influence fashion in 2026.

The players

Carolyn Bessette Kennedy

A fashion icon known for her minimalist, understated style in the 1990s.

Levi's

An American clothing company that produced the iconic 517 'Saddleman' bootcut jeans worn by Bessette Kennedy.

Natasha Halesworth

The founder of The Consistency Project, a New York-based shop that sells vintage and deadstock denim.

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What they’re saying

“Many confuse a bootcut with a traditional vintage flare; however, they are very different and not actually as wide. It's a classic straight-leg jean that can accommodate a boot, so there is a subtle, wider opening at the base of the leg.”

— Natasha Halesworth, Founder, The Consistency Project

“When I think about [Bessette Kennedy's] style, it makes total sense that this was one of her go-tos. Saddle riding history aside, there's something so feminine, [almost] sexy about the bootcut. It can transition from a casual ballet flat to a sophisticated heeled boot, making it feel versatile yet elevated.”

— Natasha Halesworth, Founder, The Consistency Project

The takeaway

Carolyn Bessette Kennedy's minimalist, understated style, including her go-to bootcut jeans, continues to influence fashion decades later. The revival of this practical yet polished silhouette shows how certain timeless pieces rarely go out of style when paired with the right pieces, making them a versatile and elevated wardrobe staple.