Caroline Bessette-Kennedy knew the media game well, after all she was a former publicist for Calvin Klein and wife of John F. Kennedy, Jr., she just chose not to play it. If her life had not been cut tragically short, Caroline would have turned 51 years old on January 7, 2017. She died in the plane crash that killed her, John and her sister Lauren nearly 18 years ago.

Caroline was effortlessly chic and stylish and super private. She dreaded paparazzi and getting paid to wear something was not her story. According to John’s long-time assistant, RoseMarie Terenzio, Caroline never accepted designer freebies.

“She always said, ‘I have to pay for it... and if not, unfortunately, I have to send it back.’”

Caroline Bessette Kennedy was born on January 7, 1966, in White Plans, New York. She stepped into a spotlight after she began dating Kennedy. Declared a trendsetter by the national press, but Bessette was was a fierce protector of her own and Kennedy's privacy. She was often compared to her late mother-in-law, Jacqueline Kennedy Onassis, because of that, as well as her work for charitable causes.

Six feet tall with long blonde hair, Bessette met and spoke with John F. Kennedy Jr. when they were both running in Central Park; she impressed him with her beauty, intelligence and sincerity. Their fairy-tale marriage in 1996 took place in a 100-year-old, flower strewn chapel on a secluded island off the Georgian coast with only 40 of their closest family and friends.

STYLE THAT LIVES

Bessette was surprisingly grounded in her approach to style. Nothing ever over the top. Magazines have described her style as “throwaway chic” and “effortful effortless.” She radiated a certain mystique whether walking NYC streets in corduroys or the red carpet at the Met Gala. Her best accessory was her smile.

“She was a whole other complex woman, says close friend Sasha Chermayeff. “The newness of the celebrity was much more shocking for her.”

"She had great dignity in the way she dressed," says Linda Wells, editor of Allure. "It was very pure. It lacked ostentation and pretention."

"She chooses simple, severe looks that not everyone would wear," Gucci designer Tom Ford told WWD. "She knows how to set off her beauty with clothes. That's a rare gift."

"She has the look of the '90s," Chanel designer Karl Lagerfeld was quoted as saying. "She is not a label girl. Everything that she wore looked fabulous on her."

"She was about more than just wearing clothes," Wells says. "There was an emotional resonance as well."