WIn the first 20 minutes of Love Story , Ryan Murphy’s new take on the often tumultuous relationship between John F. Kennedy Jr. and Caroline Bessett, the former US president’s youngest son, is depicted wearing five different hats. They include a Kangol flat cap when he cycles to a newspaper kiosk in uptown NYC, a Yankees cap when he runs topless on a treadmill to read the latest headlines about him, and a navy baseball cap when he has dinner with his mother, Jacqueline, who promptly reminds him, “No hats at the table, please.”
For Kennedy Jr., he was nicknamed “The Hunk” by the paparazzi and tabloid press, and more often than not “The Hunk Who Flunked,” thanks to the fact that this fondness for peaked caps allowed him a degree of anonymity, you might think. But he prefers to wear it behind his back, pulling the hat down over his signature flap of dark hair and showing off his full face.
Just as silk slip dresses from Calvin Klein are synonymous with Bessette, the backwards cap is now synonymous with Kennedy Jr.’s idea of how the son of a former president and first lady should dress. It’s no surprise that costume designer Rudy Manns wanted the character’s backward caps to be centered from the get-go. Less waspish, more preppy, he regularly offsets old-money cues like Armani and Calvin Klein suits, foulard ties and tweed blazers, usually in Sylvester Stallone’s over-the-top or ’90s hip-hop artist and Grivana public artist and Irvana Grivana. Grivana Grivana Grivana Public Artist and Grivana Public Artist and Grivana Grivana Grivana Artist with Simple Cap Low Wasp and Calvin Klein Suits
James Lilliefors, author of Ball Cap Nation: A Journey Through the World of America’s National Hat, says: “JFK Jr took it as a key element of his ‘high/low’ fashion look and gave it a kind of street chic, making this ‘heir of Camelot’ cool and relatable.”
Now, nearly three decades after Kennedy Jr.’s death, the backwards hat is enjoying a revival. Pinterest mood boards and social media are abuzz with images of the couple that Millennials and Gen Xers are using as styling inspiration. A shot of the duo strolling down a Manhattan sidewalk in 1996, with Bessette in a gray slip dress, black coat and suede knee-high boots, and Kennedy Jr. in a formal black suit, fat knot tie and green backwards cap, is particularly popular.
“All my problems disappear when I see a guy in a backwards hat,” reads a caption below the montage of Kennedy Jr. playing various sports above. “Watch my husband go from ‘daddy’ to ‘daddy’,” another user added as she filmed her partner flipping his turban.
Lilliefors says ’90s nostalgia was a driving force behind this backwards cap revival, but the original look goes back further than that. In the 1800s, US baseball catchers styled their caps backwards for practical reasons: they had to wear a catcher’s mask, which a forward-facing cap wouldn’t fit, but they wanted to protect their heads during long hours in the sun. By the 1990s, Seattle Mariners player Ken Griffey Jr. had it as his dugout signature.
Off the pitch, backwards caps began trending in wider popular culture thanks to Will Smith in The Fresh Prince of Bel-Air, whose denim and pastel colored 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 turned to method dressing, The Complete Unknown star wore a black backwards cap embroidered with the Bob Dylan lyrics “Don’t Think, It’s Alright”. The Super Bowl’s latest half-time star, Bad Bunny, is a badass on and off stage Likes to wear hooded caps. He follows in the footsteps of Kendrick Lamar, who topped his Chanel look at the 2023 Met Gala with a ’90s-style cap from the starter, an American brand with a high crown and signature rounded, curved brim. It’s also a look that’s snapping back on the catwalks. At the recent Ralph Lauren show in Milan, the king of preppy presented models in dark cotton caps deliberately styled backwards so the polo logo was only visible from the back.
With baseball caps now ubiquitous, seen everywhere from coffee shops to boardrooms (including on-screen versions in shows like Succession and Industry), perhaps the move toward the backwards cap represents a desire to move the trend away from the status quo. A cheap update, all it takes is a flip and the confidence to remove or turn it on.
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