The Carolyn Bessette Kennedy effect
Almost three decades after her death, Carolyn Bessette Kennedy’s style still endures—and style wannabes can learn a thing or two from one of fashion’s OG influencers.
What gives style staying power? Carolyn Bessette Kennedy, aka CBK—a former fashion executive at Calvin Klein and wife of JFK Jr.—died almost three decades ago in a private plane crash off Martha’s Vineyard that also claimed the lives of her husband and her sister, Lauren.
There aren’t many photographs of her online, yet CBK remains a perennial inspiration for fashion designers and brands, so much so that she was dubbed a “ghost influencer” by The New York Times. Check your social media feed and you’ll see CBK-inspired posts all over Instagram, while TikTok is filled with recreations of her outfits—from turtlenecks and black loafers to the perfect black dress.
Carolyn Bessette, as she was known at the time, came into the public eye in 1994 when she began dating the son of the late president John F. Kennedy and Jacqueline Kennedy Onassis. To the public, their relationship looked like another Camelot—JFK Jr. was America’s prince, while Bessette was a fixture in the fashion scene but relatively unknown compared to Kennedy Jr.
But CBK did not seek fame. The couple tried to keep their relationship private—CBK never gave interviews, and only a few voice recordings of her exist—but that didn’t lessen public interest in them. She was photographed (often without her consent) wherever she went.
Tall, with her buttery blonde hair frequently worn in a ponytail, CBK made everything look effortless, switching from casual in her Levi’s bootcut jeans to glamour in Yohji Yamamoto. Today, as a younger generation discovers her through the hit series Love Story: John F. Kennedy Jr. & Carolyn Bessette, her looks feel refreshing in a time defined by trends of the moment, constant flexing, unboxing, and algorithm-driven content.
She knew herself
It’s not the first time Carolyn’s looks have garnered media attention. Growing up in the ’90s, I would often see her style featured in various magazines; one even dubbed her the “New Jackie O.” Her style can be described as tailored, neutral and minimalist. The difference between then and now is the internet and its effect on fashion and trends. Even though she lived and died before social media existed, it has attempted to make her style accessible. However, her appeal is harder to capture because CBK seemed to resist trends to begin with.
Because CBK was a very private person and didn’t give interviews, this only added to her mystique. What people saw were her clothes. However, what made her compelling wasn’t exactly what she wore—it was the effortless attitude behind it. The online barrage of “steal CBK’s style” posts that itemize her wardrobe into a few key pieces—complete with shopping links—attempts to make her style formulaic. But this misses her very approach to fashion. She clearly wasn’t dressing for anyone other than herself, and what she wore reflected her personal taste and was practical for working women and real life.
In a fast-fashion digital age where relevance is currency, it’s difficult to replicate the look and feel of a woman’s style when she wasn’t dressing for approval to begin with.
Though little is known about CBK, this much is clear: She knew herself well. In a time dominated by conspicuous consumption and obvious cosmetic procedures, her wardrobe still resonates because of its restraint. She had a strong sense of what worked for her, wore those pieces repeatedly, and didn’t stray from them. She didn’t buy everything or follow every trend. Compared to today’s dizzying cycle of must-haves, CBK’s consistency is a reminder that style is about clarity and authenticity—that style is confidence, not endless reinvention.
Proportion and fit are important
Before her marriage, CBK worked as a publicist at Calvin Klein, which likely influenced her preference for sleek silhouettes and logo-less accessories. However simple her outfits looked, they actually weren’t—a closer look often revealed unexpected details. She favored Prada, Ann Demeulemeester, Comme des Garçons, Yohji Yamamoto, and Helmut Lang for more directional pieces. She also understood how adjusting hemlines, rolling cuffs, and refining fit could transform an outfit. Without considering your own proportions, outright copying her outfits risks looking like a cosplay version of her.
All in all, taking a cue or two from CBK isn’t about copying what she wore to the letter. It’s about finding what works for you and sticking with it. Some of the items she wore are still available for purchase—but her self-awareness isn’t. And maybe it’s that air of confidence and cool that continues to fascinate decades later.
