Say the name Carolyn Bessette-Kennedy to any discerning woman and she will wax lyrical about her stylish simplicity. Associated with classic, understated elegance, the fashion publicist’s name and incomparable style lives on and maintains societal relevance, 29 years after her untimely death. 

It was in the summer of 1999 that a black stiletto and a medicine bottle bearing the name Carolyn Bessette-Kennedy surfaced on the waves of the Atlantic Ocean. Five days later, a tragic discovery was made 40 metres beneath the waters off Martha’s Vineyard – Bessette-Kennedy, her sister Lauren Bessette, and husband John F. Kennedy Jr. had perished in a plane crash. The aircraft had been en-route to the wedding of John’s cousin Rory in Hyannisport, the Kennedys’ summer home. John F. Kennedy Jr. was at the controls, after acquiring his pilot licence only three months earlier. Despite poor visibility, he insisted on flying. With that, the once seemingly invincible power couple met their tragic end, leaving behind a decade that had defined them.

Amidst a generation of TikTokers tagging #StealthWealth and an insistent fascination with
all things ’90s, Bessette-Kennedy is still a part of the cultural zeitgeist. But how, almost 30 years after her death, is she still relevant today? Well, it started with a love story. 

The style-conscious PR consultant met the son of the former president while working as publicist for Calvin Klein in 1994. As their relationship blossomed amidst the landscapes of Central Park, Bessette-Kennedy, earning the nickname CBK, shot into the limelight. 

The couple tied the knot in September 1996 at the African Baptist Church on Cumberland Island, off the coast of Georgia. Only one photo exists of the ceremony – and it is, perhaps, one of the most famous marital images of the century. It captures the moment JFK Jr. tenderly kissed his the hand of wife, who was dressed in a silk pearl-white dress. Designed by the then relatively unknown Narciso Rodriguez, the bride opted for simplicity over opulence. The ultimate epitome of beauty – as stated in her college yearbook – CBK’s charisma was undeniable. 

Effortlessly embodying the grace of the Klein models, but with heightened elegance, Bessette-Kennedy became a media sensation. America’s answer to Princess Diana, she was cool, mysterious and sophisticated – exuding class, even in casual streetwear. 

Redefining an era of fashion, Bessette-Kennedy established what it meant to look truly ‘effortless’. Coming out of the bold-styled ’80s, an era that her mother-in-law defined in her pastel pink two-pieces, Bessette-Kennedy carved a new way for women across the world to dress. She embodied the sleek look of models such as Kate Moss but with a certain nonchalance that captivated. 

If Bessette-Kennedy were alive today, there is no doubt her style would have evolved and continued to shape fashion. However, existing in a time capsule of elegance, her minimalist luxury dress sense has never gone out of fashion. Transcending her time, age and moment in history, Bessette-Kennedy’s legacy lives on.