What Can Carolyn Bessette-Kennedy’s Style Teach Us About the Runways Today?

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During the quarter century since Carolyn Bessette-Kennedy’s tragic passing, her influence over women’s fashion has done anything but wane. For those who observed from afar, she was the pinnacle of a new kind of modern working woman—elusive, difficult to define, and hand-picked off the sales floor to handle publicity and show production by her once-employer Calvin Klein. Her enduring allure has attained a near mythological level and her personal aesthetic is frequently mimicked yet rarely successfully recreated.

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JFK Jr. and Carolyn Bessette-Kennedy in one of her signature looks, 1997.

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Bessette-Kennedy leaves the Newman’s Own George Awards in a Yohji Yamamoto ruffled coat and Comme des Garçons leather pouch, 1999.

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It would be difficult to recall Bessette-Kennedy without first referencing her iconography: her tousled blonde hair, the signature C.O. Bigelow headband, the perfect pair of Levi’s 517s, a well-tailored jacket, and her husband JFK Jr. or their dog Friday in tow. However, lesser credit is given to her affinity for the experimental, especially at that time.

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JFK Jr. and Bessette-Kennedy at the the “Bright Night Whitney” Annual Fundraising Gala, 1999.

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Yohji Yamamoto, spring 1999 ready-to-wear.

She was a lover of Prada and Miu Miu, yes, but she was also a devotee of the house of Yohji Yamamoto, one of the rebellious Japanese designers that upended the Paris set. She was an avid adapter of his subtle avant-garde, primarily shopping the current runway season. In today’s terms she was a “VIC” (a very important client) with whom the house kept a close relationship. From her fall 1998 strapless dress to her spring 1999 wrapped skirt and Yohji Yamamoto Homme button-down, these looks are frequently her most adored.

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The couple attend an event in honor of JFK Jr.’s mother, Jacqueline Kennedy Onassis, 1998.

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Yohji Yamamoto fall 1998 readytowear.

Yohji Yamamoto, fall 1998 ready-to-wear.

Photo: Condé Nast Archive

Yamamoto’s quiet-but-disruptive elegance mirrored Bessette-Kennedy’s own, and her clothing’s stoicism perhaps lent her a symbolic voice in the courtroom of public debate. (It’s not lost on many that—amid all the tabloid documentation of her life—there are only two clips of her speaking in existence, both of which are under 10 seconds.) If her choice of brand seems obvious now, it’s because a lesson in CBK’s style is, in some ways, a prominent footnote in the history of how the Japanese avant-garde altered the fashion world.

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Toteme, fall 2026 ready-to-wear.

Photo: Courtesy of Toteme
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Khaite, fall 2025 ready-to-wear.

Courtesy of Khaite

This begs the question, what could Bessette-Kennedy’s style look like today? Plenty of women still reference her as a source of inspiration and plenty of brands, including the likes of Toteme and Khaite, are enamored with that idealistic and tasteful polish. Would she have been a Phoebe Philo-ite? It’s not out of the question. After all, the British designer was and is still a pioneer of minimalist redux. Nor would it be too far of a stretch to picture her in Veronica Leoni’s Calvin Klein. As a successor to Bessette-Kennedy’s former employer, Leoni has finally brought a feminine touch to the storied New York house.

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The Row, resort 2026.

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Calvin Klein, fall 2025 ready-to-wear.

Photo: Courtesy of Calvin Klein Collection

More concretely, we can picture The Row. Mary-Kate and Ashley Olsen are known disciples of Yohji Yamamoto and have often interpreted his styles. In turn, many modern women have become disciples of them. Then there’s Marc Jacobs—an American fashion icon in his own right—whose iterations of another Japanese disruptor, Comme des Garçons, have filled the last half decade of his design. Though it’s not likely we would have seen Bessette-Kennedy in a modern day “lumps and bumps,” Jacobs’s devotion is similar proof of the Japanese avant-garde’s pervasive influence nearly 30 years on.