Even before the cameras rolled, Ryan Murphy’s forthcoming American Love Story—a new anthology series, the first installment of which will chronicle style icon Carolyn Bessette-Kennedy and political scion John F. Kennedy Jr.’s whirlwind romance—proved controversial. It was difficult to fault the casting—a smattering of promising rising stars and well-chosen big names—but the fashion? That was another matter.
Among the countless questions we have for the production team, the most pressing is: Will what we’ve seen so far be the thrust of Carolyn’s wardrobe on the show? And how will they approach adapting the style of Bessette-Kennedy’s mother-in-law, Jacqueline Kennedy Onassis, her daughter, Caroline Kennedy, or Carolyn’s boss, ’90s fixture Calvin Klein, for that matter?
As we await answers, we take a closer look at all the real-life figures set to feature in American Love Story, their distinctive styles, and the impressive actors due to play them.
Sarah Pidgeon as Carolyn Bessette-Kennedy
The striking, dark-haired, 29-year-old actor you may know from Prime Video’s The Wilds, Hulu’s Tiny Beautiful Things, or for her Tony-nominated Broadway debut in David Adjmi’s Stereophonic has gone blonde and donned slip dresses and strappy sandals to play the supremely chic fashion publicist at the center of American Love Story.
Carolyn Bessette was born in upstate New York and raised in Connecticut, modeled briefly before landing a sales job at Calvin Klein, and then worked her way up to becoming the brand’s director of publicity. She met the magnetic attorney and journalist John F. Kennedy Jr.—the only son of JFK and Jacqueline Kennedy Onassis—in 1992, when he was still dating Splash star Daryl Hannah. JFK Jr. and Bessette got together some two years later, and were trailed by paparazzi right up until their engagement in 1995. For their secret 1996 wedding, she wore a minimalist white slip dress by Narciso Rodriguez, her friend and colleague at Calvin Klein, making the designer an overnight sensation.
Married life proved to be less of a fairytale: the media maelstrom around them intensified, the couple had numerous public disagreements, and, within a few years, rumors of an impending divorce began to swirl. Then, in 1999, John, Carolyn, and her older sister, Lauren, died in a plane crash off the coast of Martha’s Vineyard after John, who was piloting the aircraft, lost control of it. Carolyn, John, and Lauren were only 33, 38, and 34, respectively. Since then, Carolyn has been revered and remembered for her work, as well as her impeccable, pared-back style—quickly becoming immortalized as an enduring symbol of effortless ’90s elegance. Just as she often refused to give interviews or be shot for magazines, her approach to fashion had a luxe-but-low-key, don’t-look-at-me quality that, ironically, made her totally irresistible to onlookers.
Paul Kelly as John F. Kennedy Jr.
Alongside Pidgeon, this relatively unknown actor is jumping on his bike with his suit and ’90s micro sunglasses to embody John F. Kennedy Jr. Ryan Murphy and his casting team reportedly auditioned more than 1,000 performers before settling on Kelly, meaning expectations are high, despite his lack of major credits or a public profile.
JFK Jr.’s early life was profoundly tragic: born just two weeks after his father was elected president, he grew up in the White House until JFK was assassinated, and attended his funeral on his third birthday. In a historic moment, the toddler was photographed stepping forward to salute his father’s casket for the final time as it was carried out of Washington DC’s St. Matthew’s Cathedral. After graduating from Brown, he went to law school, worked as an assistant district attorney in New York, and, in 1995, launched the political and society magazine George. The cover of its inaugural issue featured Cindy Crawford paying tribute to George Washington in a powdered wig and military jacket. JFK Jr.’s preppy but laidback Ivy League style was also a source of fascination.
Romantically, JFK Jr. was linked to everyone from Cindy Crawford and Madonna to Brooke Shields, Sarah Jessica Parker, and Daryl Hannah before he and Bessette tied the knot in 1996. Then, in 1999, the pair perished in a plane crash off Martha’s Vineyard. JFK Jr. had grown up wanting to become a pilot and got his license the previous year. It was concluded that he lost control of the aircraft as it descended over water at night.
Naomi Watts as Jacqueline Kennedy Onassis
The twice Oscar-nominated star of Mulholland Drive, King Kong, The Impossible, and Birdman—who is something of a veteran of the Ryan Murphy televisual universe, with parts in The Watcher, Feud: Capote vs. The Swans (for which she received both Golden Globe and Emmy nominations), and the upcoming, Kim Kardashian-led All’s Fair—is set to transform into one of the most famous women in the world. After her husband’s assassination in 1963, the pillbox-hatted and pearl-adorned first lady withdrew from the spotlight and, following the assassination of her brother-in-law, Robert F. Kennedy, married shipping magnate Aristotle Onassis and relocated to his native Greece in 1968. He died seven years later, after which Jackie returned to the US and worked as a book editor. She reportedly disapproved of her son John’s relationship with Daryl Hannah, but she’d never get to meet Carolyn—Jackie died from cancer at age 64 in 1993, before John and CBK began dating.
Grace Gummer as Caroline Kennedy
The third child of Meryl Streep and Don Gummer—who has appeared in Frances Ha, Mr. Robot, and three seasons of Ryan Murphy’s American Horror Story (Coven, Freak Show, and Delicate), and also happens to be married to Mark Ronson—is due to play the only daughter of JFK and Jackie: John’s older sister, Caroline. The latter was only five when her father was assassinated, growing up to be a lawyer and diplomat. She and her brother were very close, particularly after their mother’s death, and she was said to disapprove of his relationship with Carolyn. In the decades after her brother’s death, Caroline would serve as the US ambassador to Japan during the Obama administration and as the ambassador to Australia under Biden. She’s now 67, and married to her husband of almost four decades, artist and designer Edwin Schlossberg. The pair have three children, Rose, Tatiana, and Jack.
Sydney Lemmon as Lauren Bessette
Another notable nepo baby, the Fear the Walking Dead, Succession, and Tár star who is the granddaughter of Hollywood legend Jack Lemmon, will take the part of CBK’s older sister, Lauren. One of the closest people in Carolyn’s life, Lauren was also reportedly dating JFK Jr.’s cousin, Bobby Shriver, at the time of her death in the 1999 plane crash. (She was set to be dropped off by JFK Jr. and CBK on Martha’s Vineyard, where she’d be spending the weekend with Shriver, after which her sister and brother-in-law would go on to Massachusetts to attend a family wedding.) A highly successful financial executive who shared her sister’s love of fashion (she often wore Prada), Lauren largely avoided the spotlight during her life.
Alessandro Nivola as Calvin Klein
Carolyn’s boss, the ’90s fashion legend, will be played by the SAG-winning star of American Hustle, The Room Next Door, and The Brutalist. With his neat, neutral separates, sleek LBDs, and plush but understated outerwear—much of which was worn at events and on the streets of New York by Carolyn herself—no one better epitomized clean ’90s minimalism than Calvin. Now 82, the designer recently sat front row at his brand’s fall 2025 show in New York, the first under the helm of creative director Veronica Leoni.
Dree Hemingway as Daryl Hannah
The American model and actor—a regular in the pages of Vogue, who starred in Sean Baker’s Starlet and is the daughter of Manhattan’s Mariel Hemingway and the great-granddaughter of Ernest Hemingway—will play Hannah, JFK Jr.’s girlfriend when he first met Carolyn. A Hollywood bombshell with parts in Blade Runner, Splash, Wall Street, and Steel Magnolias already under her belt, Hannah had known JFK Jr. since their families had gone on holiday together in the early ’80s. After meeting again at the wedding of his aunt, Lee Radziwill, in 1988, the pair dated for five and a half years, even though his mother openly disapproved of the match. Early photos from the set of American Love Story show Hemingway in a boho ensemble that feels bang-on for a ’90s-era Hannah. After their break-up, Hannah went on to star in Kill Bill and, in 2018, married musician Neil Young. She is now 64 and still a regular in front of and behind the camera.
