30 Candid Photographs That Show the Coolest Looks of John F. Kennedy Jr. and Carolyn Bessette-Kennedy

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John F. Kennedy Jr. and Carolyn Bessette-Kennedy are considered one of the all time most stylish couples. Unfortunately, they both died in a plane crash 20 years ago, on July 16, 1999 but their memory lives on.

Who could forget their inimitable style? His playful beanies, her elegant and chic minimalism? Indeed, many turn to the couple for style inspiration even now.

His signature style was perfectly preppy, like his parents, but with a decidedly ’90s twist. He was most often spotted with a hat, whether it was a backward cap paired with anything from a suit to sneakers, or more inventive headwear, like berets and beanies. While the look would be a bit much on most men, he made even small sunglasses look good – although he is also known for his dapper formalwear.

Carolyn Bessette-Kennedy was similarly renowned for her style. The Calvin Klein publicist mastered ’90s fashion, managing to look as flawless in a pair of Nikes walking around Manhattan as she did in a little black dress stepping out for a formal event.

Here, below is a collection of 30 photographs that show the NY couple’s coolest looks in the 1990s:

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