What to Know
Princess Diana and Carolyn Bessette were both style icons of the ’90s who are still influencing fashion today, but that’s not all they had in common. Not only were they both private citizens who became mega famous overnight because of the men they were romantically linked to, but according to what experts told People, Diana and Carolyn were far more similar in other ways than most people think.
Princess Diana and Carolyn both joined families that were a bit hard to crack into.

Though Diana grew up in a family with royal ties, it was nothing compared to the status she suddenly had when she married then-Prince Charles, the future king of England. And for Carolyn, marrying into the Kennedy family was basically like marrying into America’s version of the royal family.
Neither family made it easy for newcomers to join, either.
“It was difficult to join these families,” Caroline Hallemann, the author of the book The Kennedys & the Windsors, told People. “There were rules and expectations coming from within the family — and from the outside world.”
Hallemann also added that, despite being in the UK, Diana looked up to Jackie Kennedy and saw her as “a real role model” as she figured out how to live a very public life as the Princess of Wales.
They were connected by very public grieving.

Not only did Diana and Carolyn both die unexpectedly at a young age — Diana at 36 in a car crash, and Carolyn (along with husband John F. Kennedy Jr. in a plane crash at 33) but their deaths also both inspired public grieving on an international level. This wasn’t something the Kennedys were new to at the time; after all, their family had lost the former president in such a shocking way while the world watched.
Diana died in 1997, less than two years before Carolyn and JFK Jr.’s deaths in 1999. After Diana’s death, author Caroline Hallemann said that Carolyn “was worried that it was going to happen to her,” and as we know now, that worry wasn’t too far off base, though this time, the paparazzi weren’t involved.
The royals and the Kennedys were also connected by the late Queen Elizabeth.

Jackie first met Queen Elizabeth during a visit to Buckingham Palace as the First Lady in 1961, and they connected over both having “great proximity to power and soft diplomacy but not true political power behind them.”
According to Caroline, they both understood what it was like to live in the spotlight, and Elizabeth even gave Jackie some advice on the subject, telling her that she needed to figure out how to “dole out your energy and take care of yourself when you’re on this public stage.”
As far as their public personas go, it seems like both Jackie and Elizabeth managed to do that perfectly. And considering the pressure that both Diana and Carolyn were under during their short lives, they both handled the frenzy around them as well as anyone could have been expected to.
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