What is it about the freakish allure of a man in a newsboy cap? They’re like the sickly siren of men’s headgear. You shouldn’t want to go near wherever the hat is—it’s somewhat perturbing at first glance—but the bizarre accessory pulls you into its floppy undertow.
Hear me out: I have a gallery of men on my phone dedicated to wearing this blooming mushroom, stiff-brimmed cap. Most are all hot older men. Perhaps the strongest endorsement comes from David Beckham, who practically lives in a herringbone version. The crown spills over from the sides, almost like rolling lava or thick melted cheese. Yet the portobello silhouette and its finite prints suit Beckham’s look; the former soccer player and father of four is a natty dresser who dons vests, cardigans, and artfully worn, very expensive leather shoes.
For the Beckhams, the hat is a family deal. Beckham’s 20-year-old son Brooklyn loves the same cap, typically wearing a gray or plaid version with weathered vintage shirts and high-waisted pants with the sprezzatura of a Pitti L’uomo show-goer. (Or maybe like an Eastern European fruit peddler from the turn of the century?)
The newsie cap can also count Hollywood god Brad Pitt as a devoted fan. The actor has flaunted a rotating collection with incarnations in shades of midnight black, slate gray, and almond milk beige. Pitt wears them just about everywhere: with his shoulders back and spine straight as he walks out of a hotel, at a basketball game, at a movie premiere, and at the airport. Other good-looking men in the hat? Idris Elba, Ryan Reynolds, and, of course, Leonardo DiCaprio.
While I’m sold on the look, I can’t say the same for everyone. I posted a beaming photo of David Beckham wearing the cap in question to my Instagram Story and asked people what they thought. The responses from men and women were numerous and mostly negative. One editor from France boldly stated, “This should be illegal,” adding, “For real, men should be fined for this.” (I’d hate to know what she thinks about men in berets!) A U.S.-based editor wrote: “Horrible, like a fedora.” Model Camilla Deterre sent me an image of a sad-looking boy from the film Oliver! with the comment: “This hat type is like a Raya song.”
Vogue contributor Diego Hadis didn’t hold back his disdain. “I understand these guys’ impulse to want to wear something other than baseball hats, especially if they’re trying to dress up,” he wrote. “But looking like a 1920s shoeshine boy might be a move in the wrong direction?” Our photo editor Becky Vu, who pulled all of the images of hot celebs in newsie hats, had a Freudian theory about why men might gravitate towards its rotund shape: “It’s phallic!” she said. “Many men are narcissists, so maybe they gravitate towards objects that look phallic.” Weird, sure, but it made me think: Are men just trying to express their unbridled masculinity by wearing a hat shaped like a faltering nuclear cloud? Who knows.
Among the DM barrage, there were some positive comments. Vogue Market Editor Alexandra Gurvitch messaged me: “I’m [down]. Love a cap!” Jason Louis Steward Jr. of the cult account formerly known as @ThatBagIsFake gave a sound analysis: “It’s a classic menswear piece that stands the test of time.” True, this hat feels like it has been around for more than a century, quite literally.
Steward Jr. has a point, too. The hat is a classic. Maybe that’s why it hasn’t been on the runways as of late, most of which have been dominated by more outré trends like animal print and fanny packs built into jackets. It’s a timeless accessory men wear when they want to look nice. Who wants to stab a ribeye on a date with a dude in a ragged baseball cap? For me, I’m still both perplexed and attracted, or mostly perplexed by my own attraction regarding the hat. It’s like one of the many men’s trends I write about, like pointy-toe shoes, the “sleazy guy” looks, male cleavage, and Bad Bunny’s overalls. It’s all so grossly sexy.
It also helps that every man I have mentioned above is very famous with a stellar jawline. After all, who else would dare to wear this bulbous creation sprouting from their head? Obviously, a man who is very sure of himself and has never seen Fiddler on the Roof.