11 of Carolyn Bessette-Kennedy's best fashion moments
Business Insider
February 19, 2026
AI-Generated Deep Dive Summary
Carolyn Bessette-Kennedy was a prominent fashion icon in the late '90s, known for her timeless, minimalist style that embodied quiet luxury with a color palette of black, white, beige, and navy blue. Her effortlessly cool aesthetic, often referred to as "cool-girl" style, gained widespread recognition during her relationship with John F. Kennedy Jr., which was chronicled in Ryan Murphy's *Love Story*. Bessette-Kennedy’s influence continues to resonate today, with her outfits frequently celebrated for their simplicity and elegance, making her a lasting figure in fashion history.
Before her tragic death in 1999, Bessette-Kennedy worked as a publicist at Calvin Klein, which likely shaped her understated yet sophisticated style. She excelled at mixing classic pieces with subtle touches like tailored jeans, flowy dresses, and structured outerwear. Her ability to blend elegance with simplicity made her stand out, whether she was attending high-profile events in black column gowns or walking the streets in casual yet chic outfits.
Bessette-Kennedy’s fashion legacy is not only a testament to her personal style but also to how her influence has endured over time. Her minimalist approach and versatile wardrobe choices continue to inspire modern fashion enthusiasts, proving that timeless elegance remains relevant across generations. For businesses in the fashion industry, her impact highlights the importance of creating designs that emphasize simplicity and longevity, aligning with contemporary trends that value authenticity and understated glamour.
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Originally published on Business Insider on 2/19/2026