Remembering the iconic John F. Kennedy Jr. & Carolyn Bessette 25 years after tragic passing — their best photos

It has been 25 years since, on July 16, 1999, John F. Kennedy and Jacqueline Kennedy's son John F. Kennedy Jr . and his wife Carolyn Bessette-Kennedy , along with her sister Lauren Bessette , were tragically killed in a plane crash.

Though John, affectionately nicknamed John-John by his family and the world, was just days away from turning three years old when his father was assassinated in November 1963 in Dallas, Texas, as the only son of the late president, many looked to him as the heir apparent to Camelot, a dream that had been further dashed by the assassination of JFK's brother Robert F. Kennedy in 1968.

In his 38 years, John followed in the footsteps of his late attorney general uncle ; he earned his law degree from New York University in 1989, and became assistant district attorney for the Manhattan DA's Office. He had gone to Brown University for his undergraduate studies, and as a student, became involved in issues concerning gun control and civil rights, as well as South African apartheid.

He also founded the political lifestyle magazine George , with Michael Berman , however two years after its launch in 1995, its popularity declined, with its co-founders at odds with each other behind-the-scenes, and it folded in 2001, two years after John's passing.

In 1992, he met Carolyn, who was born in White Plains, New York, before growing up in Greenwich, Connecticut. She graduated from Boston University in 1988 with a degree in elementary school education, though went on to work for Calvin Klein, first as a sales associate, and later as director of publicity for their flagship store.

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The couple started dating in 1994, and despite John's penchant for privacy when it came to the relationship, they immediately became the target of paparazzi and tabloids, with some of their most heartwarming, chicest but also even toughest moments, like an infamous public fight in a New York park, getting documented.

John proposed on the Fourth of July of 1995 after a year of dating, and they tied the knot with an intimate, private wedding at a small church on Cumberland Island in Georgia the following year. Few photos from the wedding exist publicly, save for some of Carolyn's trend-defining Narciso Rodríguez wedding gown.

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On July 16, 1999, they were on their way to John's cousin Rory Kennedy's wedding in Hyannis Port, dropping off Lauren in Martha's Vineyard first, when their small plane, a Piper Saratoga John was piloting, crashed into the Atlantic Ocean. John was 38, Carolyn 35, and her sister Lauren 34.

Below, revisit some of John and Carolyn's most unforgettable photos.

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TriBeCa Locals

Outside their TriBeCa apartment shortly after their wedding in 1996.

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Cool Kids

John and Carolyn were legendary for their street style.

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It Couple

At the White House Correspondents dinner in 1999, two months before their death.

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High Society

Arriving for the celebration of what would have been JFK's 80th birthday in 1997.

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The Chicest

At a fundraising event at the Whitney Museum in 1999.

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Friday Walks

The couple were parents to a dog named Friday.