Carolyn Bessette Kennedy's Iconic 90s Style Still Captivates 30 Years Later

As the new TV series 'Love Story' debuts, the fascination with CBK's minimalist yet sophisticated fashion endures.

Published on Feb. 13, 2026

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Carolyn Bessette Kennedy, who tragically died in a plane crash with her husband John F. Kennedy Jr. in 1999, has become a revered fashion icon for her effortlessly chic 90s style. Despite limited photographic evidence and her aversion to fame, CBK's pared-back yet refined aesthetic - from crisp white shirts to Levi's jeans - continues to captivate audiences and influence modern trends, with her looks described as 'timeless' and 'achievable'.

Why it matters

Carolyn Bessette Kennedy's enduring style appeal speaks to a broader cultural fascination with 90s nostalgia and the allure of the 'it girl' aesthetic. Her refusal to conform to fame and her focus on quality over quantity in her wardrobe have cemented her status as a style icon, inspiring a new generation to emulate her minimalist yet sophisticated look.

The details

Carolyn Bessette was working in PR and celebrity dressing at Calvin Klein, the coolest designer brand of the 90s, when she met and married John F. Kennedy Jr. Her wardrobe consisted of deceptively simple pieces like Levi's 517 bootcut jeans, crisp white button-down shirts, and Manolo Blahnik slingbacks. Though she was a fashion insider, she avoided the spotlight and maintained an air of mystery, which has only heightened her appeal decades later.

  • Carolyn Bessette was born on January 7, 1966 in White Plains, New York.
  • Carolyn and John F. Kennedy Jr. were married in 1996 on an island off the coast of Georgia.
  • Carolyn, John, and her sister Lauren tragically died in a plane crash in 1999.

The players

Carolyn Bessette Kennedy

The youngest of three sisters, Carolyn was a fashion insider who worked at Calvin Klein and became known for her minimalist yet sophisticated style.

John F. Kennedy Jr.

The son of President John F. Kennedy and Jacqueline Kennedy, John was married to Carolyn Bessette Kennedy until their tragic deaths in a plane crash in 1999.

Clare Waight Keller

A designer who worked with Carolyn Bessette Kennedy at Calvin Klein and described her effortless style transformation from 'super-cool street-casual to the most elegant thing you'd ever seen'.

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What’s next

The new TV series 'Love Story: John F. Kennedy Jr. & Carolyn Bessette' is now available to watch on Disney+, allowing fans to further explore the couple's iconic relationship and Carolyn's enduring fashion legacy.

The takeaway

Carolyn Bessette Kennedy's minimalist yet sophisticated style, marked by her refusal to conform to fame and focus on quality over quantity, has cemented her status as a revered fashion icon whose influence continues to be felt decades after her tragic passing. Her timeless and achievable aesthetic resonates with modern audiences seeking authenticity and a return to 90s nostalgia.