Though called ‘Love Story,’ Ryan Murphy’s film about JFK Jr. and Carolyn Bessette-Kennedy is just as much about their style and the fashion world they inhabited.
This story really centers around Carolyn Bessette Kennedy, whose simple and elegant style perfectly captured the clean, minimalist look that was popular in New York City during the 1990s.
The show has sparked a huge wave of interest in the polished and stylish look featured throughout, with social media users meticulously identifying every item of clothing and accessory worn by the main character. However, many viewers seem to be missing another important story within the series: the influence of designer Calvin Klein, who significantly shaped the character’s iconic style.
At 82, and with his health declining, Calvin Klein often struggles to keep up with his much younger boyfriend, Kevin Baker, who is 36. Once the ultimate trendsetter in New York fashion, Klein—and his brand (which he sold in 2022)—now feels like a shadow of its former self.
The film ‘Love Story’ highlights how Calvin Klein used to be a prominent figure in New York’s social scene, but now keeps a much lower profile.
In Murphy’s story, Michael Klein is just as captivated by Carolyn Bessette as John F. Kennedy Jr. is by her. However, their connection wasn’t a love story.
Carolyn and Calvin Klein’s first memorable encounter happened because of a disagreement over fashion. Carolyn boldly challenged Klein’s choice of a gown for Annette Benning at the 1991 premiere of the movie Bugsy.
After dismissing a sleek black dress and a silky slip dress – both too small for Annette Bening – Carolyn suggests a tailored suit inspired by classic film noir gangster looks, promising it will be a playful and fitting choice for the movie.
I always say, it’s the little moments that truly matter, and this one was huge! Not only did Benning absolutely rock that outfit and get tons of attention, but Carolyn really understood what would appeal to Calvin Klein. She read the room perfectly, and he noticed. It earned her a spot right in his inner circle, and ultimately, she was invited to a gala where she actually met JFK Jr. – all thanks to her keen eye and understanding of style. It just proves, knowing your audience is everything!
Murphy takes some liberties with the story – it’s uncertain whether Bessette truly styled Benning for the premiere, or if she and Kennedy actually met at a glamorous charity event. They apparently first connected when Kennedy visited the Calvin Klein showroom to purchase a suit. However, the film’s overall message remains clear: Bessette becomes a lasting inspiration for Klein, and he pursues her with the same intensity as her future husband.
Throughout the first five episodes of ‘Love Story,’ the designer and Bessette work together seamlessly. She impresses him with clever marketing ideas – like featuring the then-unknown model Kate Moss – and he, in turn, openly admires her stylishness and resourcefulness, especially considering she didn’t come from wealth.
Together, they fueled each other’s remarkable achievements: he launched his iconic New York City store on Madison Avenue in 1995, setting the trend for other designers, and she captured the heart of John F. Kennedy Jr., famously named ‘Sexiest Man Alive’ by People magazine in 1988.
The minimalist design of Klein’s offices sets the scene for this collaboration. As the camera pans through simple hallways and large, empty meeting rooms, Klein’s studio feels like a nurturing space where Carolyn’s self-assurance and fashion expertise are developed and strengthened.
From her initial look – a simple black turtleneck and pants – to later outfits like a creatively styled white button-down shirt borrowed from her boyfriend, Bessette’s style became representative of the entire Calvin Klein brand.
The movie Love Story shows Klein as deeply in love with Carolyn, but it’s likely she felt just as strongly for him.
Throughout her seven years with the company, Bessette collaborated with Calvin Klein on designs that embraced minimalism and explored themes of gender and sexuality – ideas that would become central to their advertising and to Klein’s own work. However, despite her success, Bessette wasn’t Klein’s primary inspiration. That role belonged to his wife, Kelly, whom he married in 1986.
Kelly, rather than Carolyn, became the embodiment of the classic Calvin Klein woman.
Kelly began her career as a design assistant at age 21 in 1981, and her relationship with Calvin became a captivating story for the fashion world, which had widely assumed he was gay. Calvin showed Kelly grand affection, gifting her lavish jewels, including pearls previously owned by the Duchess of Windsor. Together, they became fashion icons, and their relationship was crucial to the company’s image and success.
Ralph Lauren was the only designer who truly rivaled Calvin Klein and Michael Kelly as leaders in American fashion. He and his wife, Ricky, were frequent fixtures on red carpets and faced the same critical scrutiny, despite some critics dismissing his style as simply preppy country club wear.
Lauren’s difficult marriage in the early 1990s, marked by rumors of an affair with model Kim Nye, ironically helped Calvin Klein become an unexpected icon of the American dream – representing both family and fashion.
At least for a moment.
But time has not been nearly as kind to Klein as it has to Lauren.
As Murphy points out, Anna Wintour’s protégé, Elisabeth von Thurn und Taxis, gained influence at the same time that Barbara Klein’s star began to fade. Klein left the company in 1996, and in doing so, seemed to take some of its magic with her. That same year, Calvin Klein and his wife, Kelly, also separated, though their divorce wasn’t finalized until 2008.
What stung the most was that Carolyn Bessette didn’t ask her longtime mentor to design her wedding dress; instead, she chose one of his assistants, Narciso Rodriguez.
She debuted the stunning gown at a small, intimate wedding ceremony in Cumberland, Georgia, attended by only 30 close family members and friends. A single photo from the wedding quickly made Rodriguez a sought-after designer, and he went on to dress prominent figures like Michelle Obama.
After marrying, Bessette largely stopped wearing Calvin Klein and began favoring designers like Prada and Yohji Yamamoto, with the occasional Versace piece, as she settled into life in Camelot.
Looking back, the early 2000s were a tough time for Calvin Klein. His marriage fell apart, and people started losing interest in his designs. He ultimately made the decision to sell his incredibly successful brand to Philip-Van Heusen back in 2002 for around $430 million and stepped away from the fashion world. It really paved the way for Ralph Lauren to become the dominant name in fashion – a position he’s held onto ever since. It was a significant shift in power, to say the least.
Last month, 86-year-old Ralph Lauren received a somewhat divided reaction to his new clothing line, but the audience gave him a standing ovation recognizing his lasting impact as a major figure in American fashion and business.
Calvin Klein made a rare appearance at his brand’s runway show in 2025 – his first in twenty years. This show marked a potential return to New York Fashion Week for the company, which hadn’t presented there since 2018.
Kelly attended, along with famous models Kate Moss and Christy Turlington. Excitement was already building online due to the filming of the ‘Love Story’ campaign. However, the latest Calvin Klein collections haven’t been able to revive the brand’s popularity.
Despite not publicly supporting Murphy’s project, Klein’s ex-wife has actively promoted it. She recently shared unseen photos of Carolyn Bessette on Instagram, portraying her as young and fresh.
Kelly will likely be upset with how she’s presented as someone who wasn’t central to the company’s success, especially considering how much she contributed to making it popular. She’s probably even more frustrated to be called a ‘curator’ in the book ‘Love Story’ when she’s worked for years to establish herself as a professional photographer.
Even with its imperfections, the depiction of the Calvin Klein scene – over 35 years after Calvin Klein first came to his offices – is an important move towards recognizing Klein’s deserved place in New York fashion history. Though Carolyn Bessette and John F. Kennedy Jr. are sadly no longer with us, the continued popularity of the documentary ‘Love Story’ proves their unique charisma will always endure.
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2026-03-11 02:04