With the new Disney+ TV show Love Story having launched its first episode on February 12th, portraying the late Carolyn Bessette and JFK Jr.’s relationship, it has sparked not only younger generations’ desire for a job like Carolyn’s or a life like JFK’s, but also a fascination with the couple’s wardrobe.
The stylistic choices of the characters mimics the iconic fashion style of the 90s and of what they wore when still alive. JFK Jr. and Carolyn were not only major inspirations during their time, but are now also coming back with even more impact with the launch of the TV show. Through this revival, the show not only retells their story but reestablishes their fashion as a lasting influence on modern style.
Carolyn Bessette’s work as a publicist and fashion stylist at Calvin Klein was an almost direct reflection of her stylistic choices. She always brought poise, elegance, and most of all minimalism into her looks. And now, being portrayed by Sarah Pigeon and with the costume designer Rudy Mance, all of her amazing outfits are being brought back to life. According to Vogue, Carolyn had pieces in her wardrobe ranging from Prada, Helmut Lang, Jil Sander, Narciso Rodriguez, and Yohji Yamamoto but also more basic pieces from brands like Levis and Calvin Klein.
With little to no jewelry, always rocking a high heel or boot, and combining very simple pieces to create her looks she truly became the simplistic icon of the 90s. Her hair was also always a great part of her look, whether it was in an elegant low pony or bun, styled back with a headband, or with loose waves bringing a more relaxed feel, it always tied back to her outfit choices. Although her looks don’t seem at all revolutionary, she was able to reflect exactly what she wanted: effortless, timeless, and refined. Nowadays with the emergence of so many different styles and the uprising of minimalism, Carolyn’s looks are a point of reference for all.
While Carolyn’s minimalism defined one side of their iconic image, John F. Kennedy Jr.’s style brought a contrasting yet equally influential perspective. Although not as popular or prominent as Carolyn’s during their time, JFK Jr.’s style has recently undergone a massive resurgence, particularly with the Gen Z “Old Money” aesthetic.
While Carolyn was the queen of minimalism, John was the master of the “effortless American prep”. His style was characterized by a unique ability to mix high-end tailoring with rugged, athletic, and even streetwear elements, that create a cohesive look that looks entirely “lived-in”. Unlike the rigid power suits of the 80s, his blazers, frequently from brands like Giorgio Armani and Calvin Klein, with a more relaxed and cool fit. Beyond the courtroom and red carpets, his street style is what truly resonates today. John popularized the “off-duty” look that defined 90s Manhattan. Using the backwards cap was perhaps his most iconic accessory, and he used it even when paired with a wool overcoat or a blazer. This choice added a youthful, rebellious edge to his otherwise classic outfits.
The brilliance of JFK Jr. ‘s style lay in its lack of pretension. He never looked like he was trying too hard; his clothes were often slightly wrinkled or worn in, suggesting a man who prioritized life and movement over the mirror.
Today, as fashion moves toward “quiet luxury” and timeless silhouettes, JFK Jr. and Carolyn Bessete remain the ultimate reference for men seeking a balance between refined elegance and relaxedness. Together with Carolyn, they didn’t just wear clothes; they defined an era of sophisticated simplicity that continues to influence the runways and streets of 2026.
