Carolyn Bessette Kennedy's Timeless Take on Fashion
- UP MAGAZINE
- Feb 26
- 4 min read
By Paige Auxier
Edited by Taylor Morgan
The late Carolyn Bessette Kennedy has been a hot topic of discourse in recent weeks following the release of “Love Story,” a biographical series on FX that follows the story of her star-crossed romance with John F. Kennedy Jr. Bessette who, worked as a publicist for Calvin Klein in the early ‘90s, rose to celebrity status after entering into a public relationship with Kennedy. She was envied and admired throughout the nation for having bagged the country’s most eligible bachelor, but also for having an impeccable sense of style and an alluring air of mystery about her. A mere three years after the couple married, though, they met a tragic fate after being involved in a fatal plane crash. However, in the 26 years since the tragedy, Bessette has remained a style icon for many as her timeless taste in fashion has transcended time.
Bessette was always intentional in her wardrobe choices. Her experience working in the fashion industry gave her an understanding of how to dress herself in a way that would accentuate and complement the strengths of her natural appearance. She wore clothes with tailored silhouettes that suited her body shape and opted to sport neutral-toned items without patterns, which had greater versatility and a more timeless appearance. However, of the neutral shades she often wore, it seemed that she particularly gravitated towards black, because her fair features stood out in contrast with the dark fabric. Her meticulously curated wardrobe did not stop her from appearing effortlessly elegant, though. Her minimalist attire, especially when paired with one of her signature low-effort hairstyles and minimal makeup looks, never appeared flashy or extravagant. Her impeccable taste gave her a knack for styling outfits that cohesively incorporated designer items from luxury brands like Prada alongside casuals from mainstream retailers like Levi’s and fashion-forward pieces from avant-garde designers such as Yohji Yamamoto. She was also adamantly averse to trends; her minimalist approach to fashion was instead oriented in concepts of classic beauty and elegance, which is perhaps the key reason why her style has remained so timelessly palatable.
Bessette was known for prioritizing the quality of her clothing over its quantity. She had a plethora of Calvin Klein black basics in various styles and fabrics. She enjoyed sporting plain white tank tops and cool-toned cashmere sweaters as well. Plain, tailored button-downs were widely regarded as her signature look.
Alongside her versatile selection of tops, she wore solid, neutral-toned bottoms. Her skirts never landed above her knee and were typically purchased from Prada. Her pants, which were often from Calvin Klein or Prada, tended to have a looser fit, yet not to such an extent that they appeared baggy. She was also famous for sporting Levi’s denim in medium to light washes, particularly in their 517 style.
Her evening wear was unique, yet feminine and sophisticated. When dressing for events, she often incorporated the avant-garde designs of Yohji Yamamoto into her outfits; however, she was also known to wear items from luxury brands like Prada, Versace and Valentino. Her evening attire was incredibly pared down, which is what gave it such a unique quality. Much of what she wore, which in most instances was something along the lines of a simple black dress paired with a crisp, tailored jacket, could easily be transformed from day to night wear.
As a New Yorker, she often wore coats by necessity to bear the cool weather; however, they also served as an avenue for her to experiment with bold patterns and colors. The majority of her day-to-day coat collection was from Prada, most of which were wool and knee-length. While the dressier coats she wore to events were often black, though they varied in brand, style and fabric.
Like the rest of her wardrobe, her shoes tended to be very simple. In cooler months, she wore leather and suede boots by brands like Prada and Manolo Blahnik, all of which had at least a three-inch heel. In warmer months, though, she transitioned to wearing Prada loafers, flip flops, flats and strappy sandals, and it was through her collection of loafers that she further experimented with bold patterns and colors.
Another defining characteristic of Bessette’s personal style was her uniquely minimalistic approach to accessorising. She was rarely seen wearing any jewelry, even at events as grand as her wedding day. However, she did accessorize in other ways, especially in her day-to-day attire. For example, she often sported oval sunglasses, tortoise shell headbands and elegant silk scarves from Gucci. She was also regularly seen carrying black handbags, the most notable of which was her Hermés Birkin.
As a publicist, she knew how to use clothing as a tool to curate and maintain a desired image. Her impeccable taste assisted her in forwarding her career at Calvin Klein, but also found practical use in her personal life as she was able to implement it to exert control over how she was perceived by the public. Her muted wardrobe assisted her in blending in amongst crowds to avoid swarms of paparazzi. Like anyone else well-versed in fashion, she understood that all clothing is political. What a person wears inevitably sends a message to others about who they are, or at the very least, who they desire to be seen as. Carolyn strove to use fashion as a way to maintain her privacy. By keeping her clothing simple, she left the public with little to gauge about her character through her wardrobe, thus maintaining mystery and controlling her public image.
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