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Unpacking Carolyn Bessette-Kennedy’s Timeless Taste in Fashion

Discover the timeless elegance of Carolyn Bessette-Kennedy, a 90s fashion icon whose minimalist style continues to inspire modern trends.

Credit: Shutterstock/Matt Baron
Credit: Shutterstock/Matt Baron

It’s been 25 years since the deaths of Carolyn Bessette-Kennedy, her sister Lauren, and John F. Kennedy Jr. in a plane crash off the coast of Massachusetts. However, Carolyn Bessette-Kennedy made an unforgettable impression on the public eye, not as both John F. Kennedy Jr.’s wife and as a style icon in her own right. Her minimalist yet immaculate sense of style captivated the nation, cementing her status as one of the most stylish women of her generation.

Carolyn Bessette-Kennedy was not just John F. Kennedy Jr.’s wife; she was a fashion icon. Her timeless style frequently earned both appreciation and criticism. Despite the public attention, she protected her privacy and avoided the paparazzi. She valued privacy so much that there are only about 100 public photographs of her. This elusive character heightened the mystery surrounding her.

The revival of ’90s fashion has reignited interest in minimalist aesthetics, and Carolyn has inspired many young designers. Her ability to combine high-end pieces with affordable brands has become a go-to reference for simple, elegant looks. For example, many people now aspire to wear a designer jacket paired with vintage denim, much like Carolyn would have.

A closer look at Carolyn’s style

Carolyn Bessette-Kennedy was renowned for her ability to transition from girl-next-door casual to sophisticated uptown glamour. Her regular go-to pieces — Levi jeans and GAP T-shirts — gave the impression that her style was “relatable.” Her taste was timeless, and she chose her clothing with intention and purpose.

Bessette-Kennedy’s signature accessory, a pair of Selime Optique Aldo glasses, exemplified her minimalist approach to accessorizing. Carolyn frequently wore a tortoiseshell headband, perfect for exploring the streets of New York or attending high-profile events, which demonstrated her ability to combine flair with function.

Carolyn Bessette-Kennedy tended to wear athleisure clothing with a classic color scheme, usually going for natural hues. Before meeting JFK Jr., it was well-known that she had never bought sneakers. But because he was a well-known adventurer, she incorporated casual athleisure into her daily wardrobe. She frequently walked around Central Park with him, sporting a ponytail, a half-zip fleece, and bright Nike Air Streak sneakers.

Carolyn Bessette-Kennedy at the 1998 Fire and Ice Ball in a classic outfit.
Carolyn Bessette-Kennedy attends the 1998 Fire and Ice Ball. Credit: YouTube/@Kaitlyn Sulka

One of Carolyn Bessette-Kennedy’s well-known outfits was a Yohji Yamamoto crossover white blouse and ruffled long black taffeta skirt, which she wore to a 1999 Whitney Museum event. Bessette-Kennedy favored the Japanese designer because she admired the intricate construction of his designs.

Carolyn Bessette-Kennedy’s style embodies the influences of Yohji Yamamoto and Japanese avant-garde fashion houses like Issey Miyake and Rei Kawakubo, thereby reflecting the timeless ’90s minimalist. Carolyn was such a fan of Yamamoto that Barneys would contact her whenever the designer’s new pieces came into the shop.

The face of ’90s minimalism

The ’90s was a defining decade for fashion, marked by various styles and influential figures. Bessette-Kennedy contrasted with Kate Moss and Princess Diana, capturing different aspects of femininity and glamor. While Moss sported daily grunge-inspired ensembles and Diana embraced regal grace with dramatic flair, Bessette-Kennedy’s modest choices emphasized the beauty of simplicity and sophistication.

Bessette-Kennedy’s clean lines and understated pieces exuded a unique strength, confirming that minimalism could represent refinement. This subtle approach and her choice of timeless designs enabled her to retain her privacy while drawing significant public attention. Today, many young women mimic her style, searching for comparable pieces and incorporating them into their own style.

In the realm of fashion, Bessette-Kennedy’s appeal remains a significant part of her allure. The intention behind her outfits frequently piqued people’s interest, leaving them yearning to understand her as a person rather than a public figure. The duality of her visibility and desire for privacy creates a narrative that continues to captivate fashion enthusiasts.

The enduring legacy of Carolyn Bessette-Kennedy

Carolyn Bessette-Kennedy’s professional experience inspired her subtle yet refined approach to fashion. After graduating from Boston University, she gained experience as a publicist for Calvin Klein, where her keen eye for design flourished.

Her relationship with John F. Kennedy Jr. gave another layer to her public persona. They handled the challenges of fame together, showcasing a complementary aesthetic that was both polished and relatable. Carolyn’s ability to stay true to herself in public scrutiny, whether on a leisurely stroll in Central Park or a glamourous gala, added to her attraction as a fashion icon.

Today, nearly a quarter of a century after her passing, Carolyn Bessette-Kennedy’s legacy inspires designers and fashion enthusiasts alike. Her commitment to an effortless style and minimalism reminds us that elegance does not have to be lavish but can celebrate simplicity and intention.

As we see the resurgence of ’90s fashion, it’s essential to recognize Carolyn Bessette-Kennedy’s enormous impact on that era, which endures today. From the runway to everyday street clothes, her style philosophy has encouraged countless individuals to embrace their style and look for beauty in simplicity. While considering her achievements, it becomes evident that Carolyn was not just a fashion icon but a trailblazer whose legacy will serve as a light of simple elegance for future generations.

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