From Leonardo DiCaprio to ‘Lupin,’ the Polarizing Flat Cap Is Back

AGAINST CONSIDERABLE odds, the flat cap has conquered contemporary pop culture. These idiosyncratic, Anglo-ish sloped hats (you might know them as newsboy caps, paddy caps or golf caps) edged into the zeitgeist with the 2013 premiere of “Peaky Blinders,” the BBC drama set in post-World War I Ireland that now streams on Netflix . Since then, the flat cap’s trickle of influence has grown into a deluge. It’s a style signature of the roguish thief Assane Diop (played by Omar Sy) in “Lupin,” a Netflix series that debuted in January, and it topped off Ralph Fiennes in the recent film “The Dig.” Off-screen, too, celebs like Brad Pitt, Leonardo DiCaprio and Idris Elba seem flat-cap fixated. And one such hat even perched on the head of Tampa Bay Buccaneers coach Bruce Arians during the NFL playoffs earlier this year.

The popularity of these caps has recontextualized them. Will Bailey-Watson, 33, a university lecturer in Reading, England, noted that in years past they were “almost exclusively” worn by the elderly or tweedy countrysiders. Now, he turns on the TV and sees 30-something sports pundits all flat-capped out. Binge-watching “Lupin” convinced Mr. Bailey-Watson to sample the style himself. One recent winter day he threw on his new Ted Baker cap with a navy topcoat and a pair of Adidas sneakers. After months of lockdown slovenliness, he said the dressy cap made him feel “special,” and put a spring in his step. When he posted a photo of the outfit to his Instagram, however, his friends’ reviews were mixed. “It proved very, very divisive,” he said. The debate focused on “whether or not someone like me should be trying to pull off something like that.”

When Mr. Bailey-Watson says “someone like me” he means someone so relatively young, or someone whose job isn’t calling the Man U game on TV. The flat cap challenges average folks because it carries a lot of baggage. My female colleagues described the hats as an “immediate red flag” on men—denoting a pretentious pretender—a sentiment that women often share on social media. I’ve also seen this headwear described as hats for aging ska trombonists and caps for craft-beer nerds. Many associate them firmly with the campy 1992 Disney musical “Newsies.”

Even those who happily wear flat caps acknowledge their regrettable connotations. Mark Wood, 65, a retiree in Powell, Ohio, was given his first wool newsboy cap by an Irish-born employee about three decades ago and has worn the style since. He currently favors a wool version from San Francisco’s Goorin Bros: “It’s stylish, it’s comfortable and it’s very warm especially at this time of year.” But he has an ulterior motive. “You know, my hairline is not what it used to be,” he said, adding that he’s observed that the flat cap has “become a hat of bald men.”

When describing the caps, the under-40 fans I spoke to all used some variation of “old.” Though Austin White, 31, a digital resources coordinator at a music company in Bloomington, Ind., called the style “an old-timey hat,” he wears the flat cap he bought around a year ago frequently. A bit of a fantastical dresser, he savors its theatrical look. He said it makes him feel like an early 20th-century paperboy hollering “Extre! Extre!” or, when he wears it with a turtleneck, a poet. Flat caps don’t seem to be flying off the shelves near him: He’s the only young person he knows who owns one.


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