Discover the captivating story of Carolyn Bessette-Kennedy — from her quiet beginnings in Connecticut to becoming one of the most photographed and misunderstood figures of the 1990s.

In Part 1 of our exclusive series, we trace Carolyn’s path from a private school education and a career in fashion PR to her meteoric rise as a style icon after marrying John F. Kennedy Jr.. With her minimalist wardrobe, reserved presence, and complicated relationship with fame, Carolyn helped define an era — even as the tabloids distorted the woman behind the image.

This episode explores:

• Carolyn’s early life and family background
• Her time at Calvin Klein and immersion in 90s fashion culture
• The whirlwind romance and iconic wedding to JFK Jr.
• Her uneasy relationship with the spotlight and the Kennedy legacy
• And her resurgence as a Gen Z style muse thanks to TikTok and Instagram

💬 “She didn’t speak often, but when she walked into a room, you noticed.” – Fashion editor, 1997
 

Whether you’re a fan of celebrity history, timeless style, or the enduring mystique of the Kennedy family, this episode offers a deeper look at a woman often reduced to headlines — and why her legacy continues to resonate with audiences today.

Tell us your thoughts! Do you agree with our take? Share your take!

Support the show

• Instagram
• Patreon
• Buy Me a Coffee (one time support)
• TikTok
• Show website

If you have a judgement on any of the figures that we have covered (it can be a voice memo or an email that we can read!) or have a recommendation for a historical figure, please contact us at [email protected]!