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Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette

Decoding the mystery behind the most photographed couple of the 1990s

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s

You may not know them by name, but you have certainly seen them. They are John F. Kennedy Jr., son of JFK and Jackie Onassis, and his wife Carolyn Bassette: he tall and lanky, often immortalized in an impeccably cut suit and a pair of sunglasses, just as often photographed in casual outfits that are a perfect vocabulary of Ivy League brand preppy; she blond, sophisticated and always effortlessly elegant, perhaps the best avatar of New York chic and '90s minimalism. The Kennedy Jr.-Bassette couple is not only a pair of socialites with what is perhaps the best wardrobe since Jane Birkin and Serge Gainsbourg, but also a pair of tragic figures, who saw the end of their days prematurely, off the island of Martha's Vineyard, during a plane crash shrouded in mystery and about which numerous conspiracy theories have accumulated over the years.

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412006
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412005
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412004
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412003
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412002
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412001
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412000
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411999
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411998
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411997
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411995
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411994
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411993
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411992
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411991

About a thousand days lasted the marriage between the last prince of the American Kennedy dynasty and the brilliant Calvin Klein publicist - a thousand days filled with splendid receptions, visits to Italian designers such as Krizia and Gianni Versace, crowds of paparazzi but also family arguments, work rifts and a possible (never confirmed) cocaine addiction. Those very shots that make us adore them today (even at the time, Carolyn's style, which Michael Kors later called "throwaway chic" turned the public and magazines' heads) are the byproduct of the tabloid fury that, in life, put the couple but especially Carolyn so much in crisis. 

Portrait of a couple

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411952
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411953
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411954
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411958
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411957
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411956
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411955
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 412007
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411996

Clearly, having failed the prerequisites of their personal fame, what has remained of them in 2022 is a series of shots of them intent on walks or in the midst of social dinners and showing them in a series of incredibly perfect outfits. Speaking of the two's wardrobe, one could say that one of its constants is the mixing of low and high fashion. In a 1996 article Michael Kors summed up her style this way: «She never looks studied. I've seen her wear an inexpensive t-shirt and an expensive jacket. That shows personal expression. She doesn't tear a page out of a magazine and re-create the look. […] She has that contradiction which is very '90s: very relaxed and casual and still looking elegant». Things had not always been this way-the turning point in her style began when she started working at Calvin Klein in the late 1980s, moving over time from sales clerk to publicist. During her years at Calvin Klein, supposedly the temple of 1990s minimalism along with Prada and Jil Sander, her increasingly simple approach to dressing evolved: first her brown hair became blond; her closet filled with Yohji Yamamoto, Miu Miu, Prada, and Ann Demeulemeester; leather jackets and baggy sweaters disappeared, making way for blazers, thin long dresses, white shirts, black and camel midi skirts, Levi's jeans, and tailored coats. It was a wardrobe that was undoubtedly conservative but whose lines were so clean and essential that it would have been impossible to assign it to a specific era - the very definition of "timeless."

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411959
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411960
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411961
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411962
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411963
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411964
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411965
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411966
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411967
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411968
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411969
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411970
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411971
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411972
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411973
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411978
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411977
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411976
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411975
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411974
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411979
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411980
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411981
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411982
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411983
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411984
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411985
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411986
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411987
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411988
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411990
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411989

Of course it takes two to tango. And so one could not complete the vision of this stylish couple without John Kennedy Jr. Here is what  Elisabeth Bumiller of the The New York Times wrote about him in 1996: « Mr. Kennedy, 35, the editor of the political monthly George, grew up on Fifth Avenue but in his adult life has largely ignored his mother's Upper East Side milieu». And so he was, to better clarify the meaning of the somewhat dry phrase, the son of the so-called "first family of America," growing up amidst photographers' flashes, at state dinners, at private schools, on the private island of his stepfather, Aristotle Onassis. But John was also an adventure-loving journalist, a sportsman, a lawyer (who also failed the entrance exam twice, obviously under the watchful eye of reporters who followed him everywhere). His style was thus composed of 75 percent impeccable suits, as mentioned above, and 25 percent American-style sportswear: his outfit that includes a blue suit, a backpack carried on his shoulder, and a green cap worn backwards while carrying his bicycle remains famous. Another photo includes the same green hat, t-shirt and shorts, a waist pouch, Champion socks, and a pair of Nike shoes. Yet another depicts him intent on pedaling, the leg of his tailored pants sportingly rolled up below the knee to avoid oil stains, forked on the nose by tiny, minimalist black goggles. 

Icons of a culture in transit

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411946
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411947
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411948
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411949
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411945

It is clear that this style rests on the physical beauty and social status of both of them: in addition to being voted The Sexiest Man Alive by People in 1988, as well as having collected relationships with Madonna and Sarah Jessica Parker, Kennedy Jr. could have been a model in his youth; Carolyn, on the other hand, during her college years was indeed a model though never professionally. The two were a portrait of a certain kind of social privilege; they were handsome, wealthy, intelligent, philanthropic - yet the photos portrayed them on the street, intent on pedaling or walking, close to the common man on the sidewalks of New York. Their style made them so relatable precisely because it was a pure expression of how the upper class of the time was beginning to abandon the rigidities of the etiquette of years past, the political connections, and was beginning to embrace city life, parties, jeans, sneakers, running shorts, and the union of high and low fashion. Carolyn's jeans and T-shirts came from Gap and Levi's, some coats were salvaged from vintage stores (including the famous leopard coat worn in one of her shots), and her wardrobe was surprisingly small for a woman known as a fashion icon. Behind that style was a definite ethos: never accept gifts, never compromise with this or that brand, never waste, indeed, give away what one no longer wore. The memoirs of people close to her, especially Rosemarie Terenzio, dwell heavily on these two aspects: her famous wardrobe no larger than an ordinary closet; and her tendency to give everything away to friends and associates. Clearly we are light years away from the ethos of other celebrities both past and present.

Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411942
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411941
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411943
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411944
Love, street style and death: why we are obsessed with Kennedy Jr. and Carolyn Bessette Decoding the mystery behind the most photographed couple of the 1990s | Image 411950

Similarly, years earlier, Lady Diana had left a lasting impression on the public imagination by being photographed in a gym outfit holding a Gucci handbag - and it was to Lady D. that Carolyn was compared in both life and death. In any case, if Lady D.'s story had the overtones of tragedy, it was due to her membership in the British royal family nor are there any consistent "candid" street styles of her, Mr. and Mrs. Kennedy-Bessette were perhaps among the first celebrities to be known essentially for their personal style and to manifest themselves in the collective pop consciousness through photos taken on the street and not on the set. It could safely be said that street style became the main medium of their fame considering how Carolyn herself actively avoided interviews, press meetings, photoshoots, and any form of self-promotion-to this day there are only two clips in which her voice can be heard, and all we have left of her are the photos paparazzi took of her on the street as well as the clothes and bags she gave away before her death to people close to her. Both Carolyn and her husband John were icons of an era in transit: the modern children of an old world, who preferred the then more popular Tribeca to the aristocratic salons of Fifth Avenue, who preferred the bicycle to the chauffeur, who tried to live as private citizens when there was nothing more public than their own lives.

The charm of strangers

Given the fascination that the Kennedys-Bessettes hold over the collective imagination two decades and more after their deaths, it is strange to think that the two cultivated so much privacy. Today we know even the eating habits  of our celebrity couples, and things have reached the point where The Cut has implored Megan Fox and Machine Gun Kelly to stop sharing on social media the bizarre details of their private lives that no one needs to know. In this sense, Carolyn and John are the quintessential anti-celebrity couple - a vibe that can already be felt in their photos together. In a world where personal style no longer exists, stifled by the asphyxiating rules of the total look, the dogma of sponsored seeding and engineered outfits, their spontaneous and strangely "normal" outfit choices, without off-the-wall colors, hair dyes, tattoos and bizarre piercings, blatantly gifted luxury products and publicity stunts (such as shopping in underwear, wearing Marilyn Monroe's clothes for random reasons, drinking their partner's blood or buying the house across the street from their ex-wife's), seem to carry an authenticity that has been irretrievably lost. If today's celebrities have to jump through hoops to be seen, to be talked about, Carolyn and John wanted to disappear, to be free of the monumental shadow of the Kennedy family tree, to lead a life of pleasure but free of the spotlight, for better or worse.

Perhaps, then, the attraction we feel toward Carolyn and John is the fascination of strangers, of two mysterious figures walking down the street embraced without bothering anyone, of two people who live their lives under the flashes of photographers without wanting to turn it into a pointless three-ring circus. The reason why we still follow those two with our eyes along their walks is precisely because at their feet there are no red carpets, behind them there are no stylists, and in front of them there are no journalists pressing them with tendentious questions. There are only two people - dressed extremely well.