Why are we so obsessed with JFK Jr. and Carolyn Bessette? Decoding the mystery behind the most photographed couple of the 1990s

He tall and striking, often immortalized in an impeccably tailored suit and a pair of sunglasses, just as often photographed in casual outfits that form a perfect vocabulary of Ivy League–style preppy fashion. She blonde, sophisticated, and always effortlessly elegant, perhaps the finest avatar of New York chic and 1990s minimalism. John F. Kennedy Jr. and Carolyn Bessette are not only a pair of socialites with what is perhaps the best wardrobe since the days of Jane Birkin and Serge Gainsbourg, but also a couple of tragic figures whose lives ended prematurely, off the coast of Martha’s Vineyard, during a mysterious plane crash that over the years has generated numerous conspiracy theories.

Their story has fascinated the entire fashion system for nearly thirty years, along with cinema and pop culture, a drama that continues to captivate audiences of all ages both for the protagonists’ style and for the tragic fate they met. After endless criticism directed at director Ryan Murphy, the first three episodes of Love Story. have arrived on Disney+. A story that explores the love between Kennedy Jr. and Bessette, the role they both played in the pop culture of the time, the mechanisms of social climbing (which are still active today in New York and elsewhere), and drama - but above all, fashion.

Roughly one thousand days was the duration of the marriage between the last prince of America’s Kennedy dynasty and the brilliant Calvin Klein publicist - one thousand days filled with dazzling receptions, visits to Italian designers such as Krizia and Gianni Versace, crowds of paparazzi, but also family disagreements, professional tensions, and a possible (never confirmed) cocaine addiction. The very photographs that make us adore them today (even at the time Carolyn’s style, later defined by Michael Kors as «throwaway chic», captivated both the public and fashion magazines) were the result of that tabloid frenzy which, during their lives, placed immense pressure on the couple and especially on Carolyn.

It may have been precisely the turbulent whirlwind of Bessette’s life that made their love story so emotionally powerful as to inspire one of America’s most prominent horror and thriller directors. Caught between the fashion industry, tabloid pressure, and the expectations imposed by her role within New York high society, Bessette became one of the most controversial it-girls ever. And as we know, controversy paired with style has always appealed to both media and audiences.

A Portrait of a Couple

Speaking of their wardrobe, one could say that one of its constants is the blending of low and high fashion. In a 1996 article, Michael Kors summarized Bessette’s style as follows: «Her look never seems studied. I’ve seen her wear a cheap T-shirt with an extremely expensive jacket. It shows an ability to express herself, she’s not the type to tear a page from a magazine and recreate that look […]. She embodies that typical 1990s contradiction: very relaxed and casual yet always elegant».

Things had not always been this way, the turning point in Bessette’s style began when she started working at Calvin Klein toward the late 1980s, eventually moving from sales associate to publicist. During her years at Calvin Klein, a temple of 1990s minimalism alongside Prada and Jil Sander, her increasingly simplified approach to clothing evolved: first, her brown hair turned blonde; her wardrobe filled with Yohji Yamamoto, Miu Miu, Prada, and Ann Demeulemeester; leather jackets and oversized sweaters disappeared, making room for blazers, long slim dresses, white shirts, black and camel midi skirts, Levi’s jeans, and tailored coats. It was undoubtedly a conservative wardrobe, yet its lines were so clean and essential that it would be impossible to assign it to a specific era - the very definition of timeless.

Of course, it takes two to tango, and no vision of this stylish couple would be complete without John Kennedy Jr. Here is how Elisabeth Bumiller of the The New York Times described his personality (briefly) in 1996: «Mr. Kennedy, 35, publisher of the political monthly George, grew up on Fifth Avenue but as an adult largely ignored the Upper East Side milieu of his mother». In other words, he was the son of the so-called «first family of America», raised amid photographers’ flashes, state dinners, private schools, and on the private island of his stepfather, Aristotle Onassis.

But John was also a journalist who loved adventure and sports, as well as a lawyer (who notably failed the bar exam twice - naturally under the watchful eye of reporters who followed him everywhere). His style therefore consisted of 75% impeccable suits, as mentioned above, and 25% American-style sportswear: one famous outfit featured a blue suit, a backpack slung over his shoulder, and a green cap worn backward while carrying his bicycle. Another photo shows him in the same green cap, T-shirt and shorts, a waist pack, Champion socks, and a pair of Nikes. Yet another captures him cycling, the leg of his tailored trousers sportily rolled up below the knee to avoid oil stains, tiny minimalist black sunglasses perched on his nose.

Icons of a Culture in Transition

Clearly, this style rested on both their physical beauty and social status: in addition to being named The Sexiest Man Alive by People in 1988 and having had relationships with Madonna and Sarah Jessica Parker, Kennedy Jr. could easily have been a model in his youth; Carolyn, meanwhile, was in fact a model during her college years, though never professionally. The two were the portrait of a certain kind of social privilege: beautiful, wealthy, intelligent, philanthropic - yet photographs often showed them on the street, cycling or walking, close to the everyday New Yorker.

Their style felt so relatable precisely because it expressed how the upper class of the era was beginning to abandon the rigid etiquette of previous decades and political formalities, embracing city life, parties, jeans, sneakers, running shorts, and the fusion of high and low fashion. Bessette’s jeans and T-shirts came from Gap and Levi’s, some coats were sourced from vintage shops (including the famous leopard coat seen in one of her photos), and her wardrobe was surprisingly small for a woman known as a fashion icon.

Behind that style was a precise ethos: never accept gifts, never compromise with this or that brand, never waste - instead, give away what was no longer worn. Memories shared by those close to her, especially Rosemarie Terenzio, dwell on these aspects: her famous wardrobe no larger than an ordinary closet and her habit of giving items away to friends and collaborators. Clearly, this stands light-years away from the ethos of many celebrities, past or present.

Similarly, years earlier, Lady Diana had left a lasting impression on the collective imagination by being photographed in gym clothes while carrying a Gucci bag - and Bessette was often compared to Lady D., both in life and in death. However, while Lady Di’s story bore the tones of tragedy tied to her membership in the British royal family, and relatively few candid street-style images of her exist, the Kennedy-Bessettes were perhaps among the first celebrities to become known for their personal style and to enter pop collective consciousness through street photography rather than staged shoots.

One could easily say that street style became the primary medium of their fame, considering how Bessette actively avoided interviews, press appearances, photo shoots, and any form of self-promotion - even today only two clips exist in which her voice can be heard, and all that remains are paparazzi photographs taken on the street, along with the clothes and bags she gifted to those close to her before her death. Both were icons of an era in transition: modern heirs of an already aging world, who preferred Tribeca to the aristocratic salons of Fifth Avenue, who chose the bicycle over a chauffeur, and who tried to live as private citizens when nothing could have been more public than their lives.

The Charm of Strangers

Considering the fascination the Kennedy-Bessettes continue to exert on the collective imagination nearly thirty years after their deaths, it is striking to think how fiercely they guarded their privacy. Today we know everything about our celebrity couples, from eating habits to workout routines, from social circles to medications - all displayed on social media in accordance with influencer culture. In this sense, Carolyn and John were the ultimate anti-celebrity couple - a vibe already evident in their photographs together.

In a world where personal style no longer seems to exist, suffocated by rigid total-look rules, sponsored seeding dogma, and carefully engineered outfits, their spontaneous and strangely normal outfit choices - free from outrageous colors, extreme hair transformations, eccentric tattoos and piercings, conspicuously gifted luxury products, or publicity stunts (such as grocery shopping in underwear, wearing Marilyn Monroe’s dresses for random reasons, drinking a partner’s blood, or buying a house across from an ex-spouse) - seem to carry an authenticity that has irretrievably disappeared. While today’s celebrities must go to extraordinary lengths to be seen and talked about, Carolyn and John wanted to disappear, to free themselves from the monumental shadow of the Kennedy family tree, and to live a life of pleasures without spotlights, in both good times and bad.

Perhaps, then, the attraction we still feel toward Carolyn and John lies in the charm of strangers: two mysterious figures walking down the street arm in arm without disturbing anyone, two people living their lives under photographers’ flashes without turning them into a pointless three-ring circus. The reason we still follow them with our eyes during those walks is precisely because there are no red carpets beneath their feet, no stylists behind them, and no journalists in front of them pressing with leading questions. There are simply two people - only exceptionally well dressed.