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Fidel Castro, in signature military fatigues, being interviewed during his trip to New YorkCreditThe New York Times

It was like Sinatra headlining in Vegas. On April 21, 1959 — 60 years ago this Sunday — thousands of adoring New Yorkers gave a tumultuous welcome to a young celebrity emerging from Penn Station: Fidel Castro, leader of the Cuban guerrillas.

Less than four months earlier, he had overthrown a vicious military dictatorship after an against-all-odds campaign, and he was wildly popular in the city, drawing crowds larger than any foreign leader in its history. As throngs chanted “Fi-del, Fid-el, Fi-del,” Castro burst through police lines and began shaking hands, as if he were running for office.

It was the opening public-relations volley of a four-day victory lap that captivated New York, and it was a milestone in the history of fashion. According to Sonya Abrego, a historian of men’s fashion in the 20th century, this was the moment when what later became known as radical chic (the once-provocative use of visual markers related to militant causes that still influences what we wear today) was really born.

When Castro’s photo appeared on the front page of The New York Times after his arrival, it hardly needed a caption: He was instantly recognizable for his unique sartorial style, combining military fatigues, forage cap and unkempt beard.

His 70-strong entourage was packed with khaki-clad ex-guerrillas, whose raffish facial hair had become such a powerful symbol in Cuba that they were known simply as “los barbudos” (“the bearded ones”).

“In a way, Fidel, Che and the barbudos were the first hippies,” said Jon Lee Anderson, the author of “Che: A Revolutionary Life” and a forthcoming biography of Castro. “They burst onto the scene at the dawn of the TV age as the ultimate sexy rebels. Their sum total of their ‘look,’ with long hair and beards and berets, was potent, and it played into the cultural zeitgeist.”

Che Guevara with Lisa Howard, an ABC journalist, in Cuba in 1964.CreditElliott Erwitt/Magnum Photo

At the time, many young Americans were showing the first signs of disenchantment with what they saw as the leaden conformity of the Cold War era. Allen Ginsberg’s paean to freedom, “Howl,” was published in 1956; Jack Kerouac’s “On the Road” in 1957. “The Second Sex,” by Simone de Beauvoir, was in translation, and the civil rights movement was gaining pace.

The Cubans formed a stylistic bridge between the Beats and the 1960s counterculture, Dr. Abrego said.

“The history of fashion is not linear,” she said. “There could have easily been longhaired hippies without Che. But the impression the Cubans made on the sartorial landscape is real.” Their revolution was a most photogenic one, and the Cubans’ rebellious style infiltrated America.

The beards had been born of necessity. Castro and a band of some 20 fellow survivors from his amphibious landing in eastern Cuba in December 1956 had no razors.

But their blossoming facial topiary had quickly turned into a “badge of identity,” the leader later explained to the Spanish journalist Ignacio Ramonet, whose interviews with Castro are collected in “Fidel Castro: My Life: A Spoken Autobiography.” The accidental style was made permanent “to preserve the symbolism.”

Other elements of the revolutionary look came together during the campaign, lovingly cataloged by glossy magazines. In 1958, Fidel’s younger brother Raúl was photographed by Life sporting shoulder-length hair and a jaunty cowboy hat.

Che Guevara in what became his signature beret.CreditRia Novosti/Sputnik, via Associated Press

Photos of the mysterious, handsome Argentine-born medic Ernesto Guevara, known as Che, showed that he, too, was growing his hair long and modeling a soon-to-be-famous black beret.

And it wasn’t only men. In early 1958, a Spanish photographer traveled to the Sierra Maestra for Paris Match and came back with images that included a top guerrilla leader, the M.I.T.-educated Vilma Espín, with a white mariposa bloom behind her ear, looking like a prototype flower child.

Also featured was Celia Sánchez, the rebels’ key organizer, who had designed her own uniform with green twill tapered slacks and V-neck overblouse (according to Dickie Chapelle, one of the first American war photographers, who traveled with them).

In July 1958, Espín appeared in Life toting a rifle on her hip like Cuba’s answer to Bonnie Parker, of Bonnie and Clyde fame. In a Doris Day world on the cusp of the feminist movement, the semiotics were subversive.

Before Castro’s 1959 visit to the United States, the Cubans had hired a Madison Avenue P.R. agent, Bernard Rellin, for a princely $6,000 a month, to advise their leader on how to appeal to Americans.

Edgar Leonardo Prada Rosales, a student and fan of Che Guevara, adopted the revolutionary’s look.CreditThomas Hoepker/Magnum

When they met in Havana, Relin told Castro that the guerrillas should all cut their hair. Castro refused. He knew the power of the rebellious “barbudo” look.

It was a canny decision. By April, Castro’s so-called brand had become so renowned that an American toy company produced 100,000 forage caps with strap-on beards for kids, which were put on sale alongside Davy Crockett coonskin hats and G.I. Joe helmets.

Each was emblazoned with the black-and-red logo of the revolutionary 26th of July Movement and the words “El Libertador” (“The Liberator”), evoking the independence hero Simón Bolívar.

Castro’s four-day New York visit unfurled in a whirlwind of whiskers and khaki. His picturesque image cropped up in settings both official and touristic: He was received at City Hall by Mayor Robert F. Wagner, he greeted wide-eyed students at Columbia University, he visited The New York Times offices and he spoke to a crowd of 16,000 at the band shell in Central Park.

All of this occurred at the perfect time to influence Americans, said Nathaniel Adams, a writer who specializes in fashion subcultures. The flood of media imagery coincided with the economic boom in the West that created a new class of young consumers with disposable cash.

From left, Celia Sanchez, a confidante of Fidel Castro; Raúl Castro, the brother of Fidel Castro; and Che Guevara, during a 26th of July celebration in 1964.CreditLee Lockwood/The LIFE Images Collection, via Getty Images

“This was the first time teenagers around the world started to consciously copy each other’s styles,” Mr. Adams said. “And the fashions were being created by the kids themselves, not handed down by adults.” The highly educated Castro was like James Dean with a progressive political agenda: a rebel with a cause.

On the surface, New York’s Fidel infatuation seemed to fade relatively quickly. By the time of his next visit to the city, to address the United Nations in September 1960, Castro was derided for the same style choices that had once seemed so seductive.

The New York Daily News mocked him as “El Beardo,” or just “The Beard”; Senator Barry Goldwater lamented that the Cuban “knight in shining armor” had turned out to be “a bum without a shave.” Before long, some Americans buzz cuts were staging anti-hippie rallies, holding placards with sayings like “Long Hair Is Communism.”

But Castro’s influence on fashion would endure. For his 1960 New York visit, he and his entourage moved on from white middle-class America and decamped to a Harlem hotel, the Theresa, where they met Malcolm X and other black leaders.

This time, the style highlight was a cocktail party in the ballroom organized by the progressive group Fair Play for Cuba and attended by 250 bohemian luminaries, including the poets Allen Ginsberg and Langston Hughes, the photographer Henri Cartier-Bresson and an array of civil rights activists.

Fidel Castro’s army chief of staff, Major Juan Almeida, left, and Captain Antonio Nunez Jimenez, head of Cuba’s National Agrarian Reform Institute, at the Hotel Theresa in Harlem, when the Cubans met the leaders of the black empowerment movement and other civil rights activists.CreditWilliam N. Jacobellis/NYP Holdings, Inc., via Getty Images

“The proletarian staff of the hotel, the olive green uniform of the ‘guerilleros,’ the general lack of formality, all helped to emphasize the gaiety and the stimulating, if not revolutionary, character of the meeting,” wrote one guest, the European journalist K.S. Karol, of the party.

Ten years later, Tom Wolfe coined the term “radical chic” to mock New York intellectuals who were hypnotized by revolutionary fashions at a party hosted by Leonard Bernstein for the Black Panthers — who, of course, had taken the paramilitary look from the Cubans and made it their own.

Since then, fashion has only further denatured the style, and now camo pants are available everywhere from Old Navy to Balmain.

“‘Radical chic’ is a term that seems so 20th century,” Ms. Abrego said. “It was once very negative, referring to a style that developed organically, but has been appropriated as a fashionable look without any further political commentary or personal risk. I struggle to explain it to kids wearing Che T-shirts today.”