Style icons John F. Kennedy Jr. and Carolyn Bessette

John F. Kennedy Jr. grew up in the most mythologized political family in the United States, the son of President JFK. Public life was not something he “stepped into” – it was there from day one, when he was born in 1960. He trained as a lawyer and was the editor-in-chief of the political magazine George.

In 1992, he met Carolyn Bessette, a PR executive at Calvin Klein, who later became his wife. With her background in the fashion world, she had already developed a clear sense of aesthetics, something that would quickly come to define how the couple was perceived publicly.

Throughout the 1990s, they were constantly pursued by paparazzi. The combination of the Kennedy name, a much-discussed and at times tumultuous relationship, along with their distinctive style made them a natural focus in the media.

John F. Kennedy Jr. personified a relaxed, classic American preppy style, while Carolyn Bessette-Kennedy represented a more stripped-down and minimalist aesthetic.

Their visual interplay – where tradition met the uncomplicated style ideals of the '90s – helped cement their status as style references, far beyond their time. However, their high-profile relationship met a tragic end in 1999, when the couple perished in a plane crash.

As part of the political dynasty, John F. Kennedy Jr. also dressed accordingly: well-fitted tailored blue or gray suits, a pair of brown or black oxfords, ties, and crisp white or blue shirts, often from American brands. Here is the couple on their way back from their honeymoon in Turkey and Greece in 1996.

The style that JFK Jr. wore was also characterized by American style markers such as blue straight Levi’s jeans, sneakers, and a baseball cap. One of his trademarks was the backward-facing newsboy cap that he often wore as headgear. He frequently mixed a tailored clothing style with sporty or casual details. It was not uncommon to see him in a suit, with the cap or newsboy cap worn backward, and a pair of sporty sunglasses while cycling. Carolyn carries her Birkin, which is often associated with her. Here, they stroll in Tribeca, New York, in 1999.

Beyond the political bureaucracy and well-tailored suits in the elegant salons, a more relaxed take on classic American 90s leisure is emerging. Here we see John F. Kennedy Jr. with Carolyn Bessette on the streets of New York, buying the newspaper, once again sporting the backward flat cap, a waist bag, linen shorts, a pair of white sneakers with high white tube socks, and a bowling shirt, 1996.