When photographs appeared online last summer of Paul Anthony Kelly and Sarah Pidgeon in costume as John F. Kennedy Jr. and Carolyn Bessette for the new Ryan Murphy series Love Story, it became very apparent very quickly that the details of the couple’s lives, and their clothes in particular, remain a topic on which people have very strong opinions. Eight months—and one replaced costume designer—later, the wait for the show is finally over.
The nine-episode series, which premiered with a three-episode drop this week, focuses on Kennedy and Bessette’s tumultuous relationship—with each other, with the Kennedy family, and with the ever-present paparazzi—between their first meeting in 1992 and their tragic deaths in a 1999 plane crash. As the son of President John F. Kennedy and Jaqueline Kennedy Onassis, JFK Jr. was as close to royalty as it gets on this side of the Atlantic. He was also one of the most eligible bachelors in Manhattan, having dated Darryl Hannah and Madonna before marrying Bessette. Bessette, meanwhile, was a rising star at Calvin Klein, first as a sales associate and then as the director of publicity, whose inimitable NYC cool-girl style helped to shape the brand’s look through its most influential era. Integral to their mystique, of course, was how effortlessly stylish they both were (albeit in completely different ways) and how much fashion history intersected with their story. Given those bona fides, and the current zeitgeist of ’90s nostalgia, it’s hardly surprising that the pair’s lives remain as fascinating in 2026 as they did three decades ago.
There’s much more to the story, however, than the pair’s perennially mood-boarded looks. After bingeing the first three episodes, here’s our take on how a few of the show’s more notable style-adjacent cultural moments stack up with the true story.
Maybe. There are varying theories about how the couple met, but none of them precisely lines up with the version depicted in the show, in which Calvin Klein acts as matchmaker at a black-tie fundraising party for the Amazon rainforest. Specifically, Klein, portrayed by Alessandro Nivola, tells Carolyn, “You’re gonna thank me for this,” right before he makes an introduction. According to JFK Jr.: An Intimate Oral Biography by RoseMarie Terenzio and Liz McNeil, JFK Jr. is said to have clocked Bessette at a party thrown by Naked Angels, a NYC theater company around this time, but what seems certain is that Calvin Klein was integral to their meeting. Per both that book and Once Upon a Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller, Klein chose Bessette, who worked in VIP sales, to fit JFK Jr. for a suit at the brand’s showroom (as in episode one), despite the fact that she usually worked on the women’s side.
Very much so. For a man with such a luscious head of hair, JFK Jr. spent a surprising amount of time wearing hats. These included (but are by no means limited to) backwards baseball caps, an array of knit beanies, and several berets. Among his more outré choices was a rotation of Peaky Blinders–esque flat caps, worn backwards, à la Samuel L. Jackson. While we don’t have photographic evidence of him wearing a flat cap with a jacket and tie (as he does for his fateful meeting with CBK at the Calvin Klein showroom in American Love Story), there are plenty of shots of him walking around NYC wearing one.
No. But she did help her become the face of Calvin Klein. In the first episode of American Love Story, Carolyn Bessette pulls Kate Moss’s headshot out of a pile of rejected photos on Calvin Klein’s desk. Bessette is said to have helped create the look of Calvin Klein’s CK One era, and among her greatest contributions was lobbying—along with art director Fabien Baron—for a then-unknown Kate Moss to appear in a 1992 underwear ad alongside Mark Wahlberg. The resulting TV ad is, to put it in the kindest possible terms, a great reminder that we’ve come a long way as a society in the last 30 years, but it would launch Moss’s career. She would soon go on to become the face of Obsession, and a definitive influence in 1990s fashion in her own right.
Yup! But that wasn't the only place JFK Jr. worked out. While he may or may not have ever taken an aerobics class with Elaine Benes, JFK Jr. spent a lot of time at the gym by all accounts. American Love Story does, too, and the staffer who pops up wearing an Equinox tee in episode two isn’t an anachronism. The high-end fitness chain, which now operates 115 gyms worldwide, launched in 1991 with a single location on Amsterdam at 76th Street in Manhattan’s Upper West Side. According to Judy Taylor, the club's SVP of PR and philanthropy, JFK Jr. joined the club around 1994. But he probably didn't run shirtless on the treadmill there, as he does in the opening of episode one—it was, and is, against club policy. He was also frequently seen at the former Downtown Athletic Club in the Financial District, which was much closer to his Tribeca loft (and more consistent with the plot of that Seinfeld episode). He would later become a member of the famed New York Athletic Club in Midtown, too.
He sure did. Part of what made JFK Jr. one of the most photographed men of the 1990s (not to mention People’s Sexiest Man Alive) was his larger-than-life style. His snatched jawline and perfectly textured flow didn’t hurt, of course, but from the way he wore his clothes to his penchant for playing football shirtless in Central Park, he rarely did anything in a conventional way. That includes his preferred mode of transportation: the mountain bike. Per the opening of American Love Story, which includes a copy of GQ from May 1992 on a newsstand, Kennedy’s commuting outfit included a suit, a red backpack, a pair of wire-rimmed shades, and a giant bike chain worn as a belt. Despite this, he’d often forget to lock it up, and was infamous for having his bikes stolen, as depicted at the end of their first date in episode one.