CAROLYN BESSETTE & JFK JR.

CAROLYN BESSETTE & JFK JR.

STYLE, ETERNAL:

CAROLYN BESSETTE AND JFK JR.

A look that defined an era, and a romance that went down in history.

WORDS: TOM KEOWN

In the 25-plus years since Carolyn Bessette-Kennedy died, her influence only continues to intensify. Difficult to define yet instantly recognisable, her style is the opposite of nostalgia. A quick search of her name yields endless think pieces (such as this one) attempting to decode the enduring appeal of her wardrobe – one that feels remarkably aligned to the modern woman. Fashion critics often attribute this to the space she occupied: poised somewhere between the attainable and something much more obscure.

A publicist at Calvin Klein, Bessette-Kennedy's style could be seen as a construction of key components. Her wardrobe distilled the essence of downtown 1990s Manhattan dressing: disciplined silhouettes, a subdued colour palette, and an unwavering reliance on foundational pieces – blue jeans, the perfect white shirt, bias-cut slips. Although intensely private, it would be naïve to ignore the role her marriage to John F. Kennedy Jr. played in amplifying her image. Like Marilyn Monroe before her, Bessette-Kennedy’s aesthetic accrued a cultural currency that ultimately eclipsed the woman herself. It’s the stuff of American legend: where Marilyn had her white halterneck dress, Carolyn had her tortoiseshell headband and Prada bag.

But to reduce Bessette-Kennedy to iconography alone would be a disservice. Her simplicity was only ever surface level; it takes a great deal of precision to look so effortless. Alongside her Levi’s 517s and her headbands she stocked up on from New York apothecary C.O. Bigelow, Bessette-Kennedy also had a penchant for collecting Yohji Yamamoto, Jil Sander, and Prada. She had an exacting eye, and it was her knack for exploring tensions through what she wore that makes her fashion so compelling. As the newly-released TV show Love Story: John F. Kennedy Jr. and Carolyn Bessette has reignited the public's fascination with the couple, we return to the now mythical paparazzi images that documented not only their romance, but the quiet power that comes with perfecting a personal style.

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Unsure who you want to be once winter finally ends? Consider Carolyn Bessette-Kennedy, captured mid-stride in Manhattan, dog in tow. In denim cut to perfection and the perfect strappy sandal, she proves that warm-weather dressing doesn’t need to reinvent the wheel – only to refine it.



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CBK consistently offers a lesson in enviable daytime dressing. Candid images of her are testament to the fact that when the foundations are solid, everything tends to fall into place. In other words: once you’ve curated your own impossibly chic capsule wardrobe, you can't help but look the part. Even if the day’s activities don’t extend far beyond lounging around the neighbourhood.

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However, anyone familiar with the lore of CBK will be quick to tell you - ‘lounging’ is not something her legacy is synonymous with. She was a career girl through and through; much of her enduring appeal lies in her refusal to let her identity be defined by the political dynasty she married into.

Her preferred uniform for elevating the 9-5 grind? Tailored outerwear, artfully beat-up leather, boots that could be relied on to take her from subway to office in a time crunch. And the final ingredient: always a generous serving of black.

There is something remarkable about a style that feels modern no matter how many years pass. For me, that discovery was Carolyn Bessette-Kennedy.

- Sunita Kumar Nair (author of CBK: A Life in Fashion)
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An unfailingly aesthetically pleasing pair, Carolyn Bessette-Kennedy and John F. Kennedy Jr. always balanced each other out perfectly. CBK was ‘90s modernism in motion, all clean lines and an urban disposition. JFK Jr., however, offered something more vintage and relaxed. He displayed his pedigree through the unbothered way he inhabited his clothing; be it sporty jersey when on his bike or the ultimate tuxedo at a black tie event. There were times when the couple’s outfits mirrored each other’s almost exactly, but it was more fun when they displayed their differences more visibly.

JFK Jr.’s style is as timeless as his wife’s. In fact, Jonathan Anderson looked to him for inspiration when costuming the 2024 film Challengers; set mainly in American country clubs and tennis courts. When asked about channelling JFK Jr’s nonchalant, ‘Old Money’ aesthetic for the film’s male stars, Anderson said:

"When JFK Jr. was younger, in the ‘80s and ‘90s, there was kind of an effortlessness to his wardrobe — like he could wear anything, and sex appeal would always be there.”

One half of a couple that ruled the ‘90s New York social scene, CBK applied the same uncompromising vision to her eveningwear that she did her everyday looks. In a sea of excess, she stood out immediately thanks to her commitment to a pared back approach, regardless of the night’s occasion. Famously known for never wearing jewellery, CBK let the look’s silhouette speak for itself; undiluted and unadorned.

There’s a lesson here we can all learn. When you’re already late, the look starts to feel overwhelming and there’s too many moving parts, the smoothest, coolest solution is to simplify it down to its essence.

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Author: Author - - Photographer: Photographer

In photographs, she [CBK] always appeared quite cool and aloof, but in person she was exactly the opposite... She was polished and slick, yet she had great charm and, of course, great style. She was an individual. She was a true beauty.

- Tom Ford

CBK will forever remain an enigma. Although so much of her life played out in front of the world’s cameras, the woman herself remains carefully guarded. Her wardrobe remains the most vivid expression of self she ever offered, and perhaps that’s exactly how she always intended it.

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