Carolyn Bessette-Kennedy is one of several historical figures known for their outstanding fashion sense. While many people know Bessett-Kennedy for her marriage to JFK Jr., individuals in the fashion industry regard the late publicist first and foremost as a style icon. The accolade could be attributed to her stint as a Calvin Klein executive, but it’s more probable that her seamless polish was a natural trait.
In an exclusive interview with InStyle, fashion stylist and style expert Naina Singla describes how Bessette-Kennedy’s style was based on three pillars: simplicity, refinement, and sophistication. “Besette-Kennedy had a versatile collection of basics and cherished pieces,” Singla tells me. “Rather than following the current fashion trends, she stuck to her distinctive timeless style and preferred structured designs that worked for her physique. “She dressed for herself and did whatever made her happy.”
In June 2025, American writer and director Ryan Murphy revealed on Instagram that the first chapter of his new series, American Love Story, will center on the romance of John F. Kennedy Jr. and Carolyn Bessette-Kennedy. Before its scheduled publication in February 2026, audiences have begun to reflect on Bessette-Kennedy’s effortless elegance and lasting sartorial effect.
The publicist’s emphasis on fundamentals, capsule wardrobes, and a neutral color palette contributed to her timeless style. Fortunately, her ageless grace is simple to recreate—here’s how.
What is in black and white everywhere? Bessette Kennedy’s daily clothing rotation. According to paparazzi images, the ’90s icon had an extensive collection of black tops appropriate for any occasion. She had at least one of each: long sleeves, short sleeves, sleeveless, V-neck, crewneck, and turtleneck.
“Slip dresses were one of Bessette-Kennedy’s favorite go-to pieces,” Singla explains; “and the 90’s minimalist trend is popular right now.” This dress shape is ideal because it can be easily layered for cooler weather or worn as a slip throughout the summer.
A pristine white button-down is a staple in capsule outfits, particularly Bessette-Kennedy’s. She’d wear a tailored fit with trousers, jeans, or a midi-length skirt during the daytime. Nonetheless, one of Bessette-Kennedy’s numerous stylistic skills was her ability to elevate fundamentals. She achieved this in such a way that something simple and often used for casual wear was easily transformed into formal clothes. The white button-down was no different. On the night of the 1999 “Brite Nite Whitney” fundraising event at the Whitney Museum of American Art, she expertly tucked the top into a black, floor-grazing skirt, accessorized with sandals and a golden clutch.
