Within the first 20 minutes of Love Story, Ryan Murphy’s new take on the often tumultuous relationship between John F Kennedy Jr and Carolyn Bessette, the youngest son of the former US president is depicted wearing five different caps. They include a Kangol flat cap as he cycles to a newspaper kiosk in uptown NYC to read the latest headlines about himself, a Yankees cap as he runs topless on a treadmill and a navy baseball cap as he joins his mother, Jacqueline, for dinner, where she promptly reminds him “no hats at the table, please”.
For Kennedy Jr, hounded by the paparazzi and tabloid press who nicknamed him “The Hunk” and more often than not “The Hunk Who Flunked”, you might think this penchant for peaked caps was thanks to the fact that they let him go somewhat incognito. But he preferred to wear his backwards, pulling the cap downwards over his signature flop of lush black hair, and leaving his full face on view.
Just like silk slip dresses from Calvin Klein were synonymous with Bessette, a backwards cap has now become synonymous with Kennedy Jr, who toyed with the idea of how the son of a former president and first lady should dress. It’s no wonder costume designer Rudy Mance wanted to centre the character’s backward caps from the get-go. Less waspy, more preppy, he regularly offset old-money signifiers such as formal Armani and Calvin Klein suits, foulard ties and tweed blazers with a casual cap worn in a way more typically seen on Sylvester Stallone in Over The Top, or on the likes of 90s hip-hop stars Public Enemy and grunge artists Nirvana.
James Lilliefors, author of Ball Cap Nation: A Journey Through the World of America’s National Hat, says: “JFK Jr adopted it, and adapted it, as a key aspect of his ‘high/low’ fashion look, giving it a kind of street chic and making this ‘heir to Camelot’ both cool and relatable.”
Now, nearly three decades after Kennedy Jr’s death, the backwards cap is having a resurgence. Pinterest mood boards and social media are awash with images of the couple that millennials and gen Zers are using as styling inspiration. One shot of the duo taken in 1996 as they stroll down a Manhattan sidewalk, with Bessette in a grey slip dress, black coat and suede knee-high boots and Kennedy Jr in a formal black suit, fat knotted tie and green backwards cap, is particularly popular.
“All my problems fade away when I see a man in a backwards cap,” reads one caption below a montage of Kennedy Jr sporting a variety of the aforementioned. “Watch my husband go from ‘dad’ to ‘daddy’,” adds another user as she films her partner turning his headwear around.
Lilliefors says 90s nostalgia is a driving force for this backwards cap revival but the original look goes much further back then that. During the 1800s, US baseball catchers styled their caps backwards for practical reasons: they needed to wear a catcher’s mask, which a forward-facing cap wouldn’t fit over, but they still wanted to protect their heads during the long hours spent in the sun. By the 1990s, the Seattle Mariners player Ken Griffey Jr had made it his dugout signature.
Away from the pitch, backwards caps began to trend in wider popular culture thanks to Will Smith in The Fresh Prince of Bel-Air, where denim and pastel coloured caps captured his easy but rebellious style. Around the same time, hip-hop artists including Jay-Z, and Limp Bizkit’s Fred Durst, were rarely seen bouncing around on MTV without one.
Fast forward to today and celebrities can’t get enough of the flip and reverse method. In January, as Timothée Chalamet leaned into method dressing, The Complete Unknown star wore a black backwards cap embroidered with the Bob Dylan lyrics “Don’t Think Twice, It’s Alright”. The Super Bowl’s latest half-time star, Bad Bunny, likes to wear backwards caps on and off stage. He follows in the footsteps of Kendrick Lamar, who has championed them ever since he topped off his Chanel look at the 2023 Met Gala with a 90s-style cap from Starter, an American brand that has made a high crown and a rounded, curved brim its signature. It’s also a look that is snapping back on the catwalks. At a recent Ralph Lauren show in Milan, the king of prep presented models in brightly coloured cotton caps deliberately styled backwards so the Polo logo was only visible from behind.
With baseball caps now ubiquitous, seen everywhere from coffee shops to boardrooms (including on-screen versions in shows such as Succession and Industry), perhaps the move towards the backward cap hints at a desire to move the trend on from the status quo. A cheap update, all it takes is one flip and the confidence to pull it off or on.
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