“Goodbye, sweet hat.”
—Lewis Carroll, Alice’s Adventures in Wonderland

There once was a time when you never saw a man on the street without a hat. To be hatless was to be half dressed—and it had to be the right hat. But what was the right hat? Well, you couldn’t go wrong with a Borsalino fedora.

“The 40s was a great era for big beautiful Borsalinos on big, beautiful men,” the costume designer Deborah Nadoolman Landis said in the 2015 documentary Borsalino City. “Just look at Humphrey Bogart in Casablanca.” In their last, sublime close-up, Ingrid Bergman is in her traveling hat and Bogart is in his Borsalino. “They’re two hats in love,” in Landis’s description.

Think of Jean-Paul Belmondo on a Paris street in Breathless (1960), in his wide-brimmed fedora, drawing his thumb across his lip while studying a photograph of Bogart. In 1963, Marcello Mastroianni channeled Fellini in a Borsalino in 8 ½, and Toni Servillo wears one in The Great Beauty (2013).

Humphrey Bogart and Ingrid Bergman in Casablanca, 1942.

Harrison Ford in Raiders of the Lost Ark, Robert Redford in The Great Gatsby, Robert De Niro in Once upon a Time in America, Al Pacino in The Godfather, Michael Jackson in his “Billie Jean” and “Smooth Criminal” music videos: they all wore Borsalinos.

But Borsalino’s best-known customer may have been Al Capone. Having grown up in thrall to Westerns—Tom Mix in his white hat—the prince of Chicago’s meanest streets crowned himself with a white Borsalino. Capone wore it at an angle, in the Italian tradition of the bella figura, the proud, impeccably dressed Italian man who everyone knows has power.

“The Most Beautiful Hats in the World”

In 1857, Giuseppe Borsalino set up his hatmaking workshop in Alessandria, Italy, with the help of his brother Lazzaro. Giuseppe was just 23, but he had already been at work for seven years, learning his trade as a master hatter in Paris. Named the Borsalino Giuseppe & Fratello Spa, it was so successful that for three generations just about everyone in Alessandria worked at the Borsalino hat factory. The townspeople could time their day by the factory whistle and gaze up at the chimney with “Borsalino” scrolled around its highest point like a tower in a tale of Boccaccio.

Initially, the Borsalino was a bowler, then a homburg, then a fedora, when Giuseppe pinched the front of the hat, creating two dents that allowed the wearer to easily tip his hat to a lady. In 1900, Borsalino’s soft felt fedora with its pinched shape was awarded the Grand Prix for design at the Universal Exposition in Paris. More honors would follow: Official Supplier for the Royal House of Savoy in 1939; the Coupe d’Or Bon Goût Français for “the Most Beautiful Hats in the World” in 1963; and in 2017, the Italian government issued an official postage stamp celebrating the 160th anniversary of the Borsalino hat company.

Borsalino’s best-known customer may have been Al Capone.

In 1970, Borsalino became the first luxury brand to lend its name to a film. Set in the 1930s, the movie was adapted from The Bandits of Marseille, by Eugène Saccomano. But Alain Delon, who both starred in and produced the film, had to promise Paul Cabone and François Spirito—the real gangsters on whom Saccomano’s novel was based—that they wouldn’t use their real names, nor show them collaborating with the Nazis. Just to be safe, they changed the title. It was Delon’s idea during lunch one day with the director. “Borsalino!” he said. “What do you think? The Borsalino hats! Génial, non?”

Eddie Muller, the knowledgeable, dressed-to-kill host of Turner Classic Movies’ Noir Alley, remembers seeing Borsalino when it first came out. “It was the French equivalent of The Sting,” says Muller, “where you put Robert Redford and Paul Newman in these beautiful vintage clothes. That’s kind of the point, just to see these guys dressed like that.”

In their last, sublime close-up, Ingrid Bergman is in her traveling hat and Bogart is in his Borsalino. “They’re two hats in love.”

But Borsalinos weren’t just relegated to film noir, which Muller defines as “suffering with style.” The hero in Federico Fellini’s 8 ½, played with sublime ennui by Marcello Mastroianni, is a film director named Guido Anselmi. “Guido” means “guide”; “anselmi” means “helmet of the gods,” a reference perhaps to the black Borsalino that Fellini rarely went without, and that Mastroianni wore in the film—even in the bathtub. The film’s title represented the number of films Fellini had made—seven features and two short subjects—and, possibly, the director’s hat size. For a time, the New York hatters Worth & Worth sold “the Fellini.”

Marcello Mastroianni in Fellini’s 1963 film, 8 ½, which was titled after the director’s hat size.

Redford saw 8 ½ when he was appearing on Broadway in Barefoot in the Park. “I love Fellini’s work, and I particularly like that movie, but one of the things that stuck out in that film was [Mastroianni’s] hat,” he recalled later. “I kind of fell in love with this hat.” Redford wanted one just like it for The Great Gatsby. After more than a year of searching in vain, he wrote to the head of the Borsalino company. “You may remember me. My name is Robert Redford. We met in New York when you presented me with a Bors hat from 8 ½.... I want very much to have another hat, the same kind, black this time. I would like to get one with the brim slightly larger.” Eventually he traveled to the factory in Italy and pointed to the one he wanted, with his family waiting in the car outside.

When the costume designer Christine Bean started work on the pilot for The Blacklist, she collaborated closely with its star, James Spader, to design the look of his character, Raymond Reddington. “I wanted him to have a timeless silhouette,” she says, “and the three-piece suit became his signature look … with the Borsalino topping it off.” At first the show-runners were hesitant about casting Spader’s face in shadow, but they came around to believing “that the fedora was the essential element” in creating that character. When you see a fedora in a film or TV show, Bean says, “it communicates who that character is before the actor even says a line.”

Fashions changed—dramatically—in January of 1961, when John F. Kennedy was inaugurated president of the United States without wearing a hat. Soon, hippies were growing their hair, letting their freak flags fly. One of the Borsalino heirs, commenting on how long-haired men no longer favored the Borsalino, remarked, “A man has lost the pleasure of taking his hat off in front of a lady.”

Jean-Paul Belmondo and Jean Seberg in Breathless, 1960.

By 1987, the Borsalino factory was closed and sold to a group of Italian investors. The family hoped that the new owners would at least preserve the smokestack bearing the family name, but that, too, was eventually razed. A week before Christmas in 2017, a court in Alessandria declared the Borsalino Giuseppe & Fratello Spa bankrupt. Haeres Equita, a private-equity fund, walked off with what was left of Borsalino.

On avenues and boulevards and along the strands, the Borsalino has been admired in front of storefront windows and waved from the decks of ocean liners; they’ve been through wars and at the funerals of kings. All that elegant history is behind glass now; you can see it for yourself at the Borsalino Hat Museum, which opened last year in one of the old factory buildings. But don’t look for the proud chimney with the scripted word “Borsalino” perpetually unfurled at the summit. Like the era of the hat it gave its name to, it’s gone.

Sam Kashner is a Writer at Large at AIR MAIL. Previously a contributing editor at Vanity Fair, he is the author or co-author of several books, including Sinatraland: A Novel, When I Was Cool: My Life at the Jack Kerouac School, and Life Isn’t Everything: Mike Nichols, As Remembered by 150 of His Closest Friends