On a frigid New York afternoon in February 1963, Bob Dylan posed with his girlfriend at the time, Suze Rotolo, for the portrait that would appear as the cover of his second album, “The Freewheelin’ Bob Dylan.” He had chosen his rumpled clothes with care, Ms. Rotolo noted in her memoir. The outfit included one of his favorite items: a tan suede jacket. “It was an ‘image’ choice,” Ms. Rotolo wrote, “because that jacket was not remotely suited for the weather.”

During the photo session that day, the singer was able to pull off the trick of constructing an alluring public image for himself while giving the impression that he didn’t care too much about how he came across. Sixty years on, his talent as a photographic subject is on full display once again in the portraits that are part of a new ad campaign for the fashion brand Céline Homme.

The enduring “Freewheelin’” portrait, shot by Don Hunstein, had a hypnotic effect on early Dylan fans. The historian Sean Wilentz, a teenager when the album came out, saw it as “a picture that, with its hip sexiness, was more arousing than anything I’d glimpsed in furtive schoolboy copies of Playboy,” he wrote in his 2010 book, “Bob Dylan in America.”

Mr. Dylan also understood the power of that image: When he handed out advance copies of the record jacket to friends in the spring of 1963, he said, “The cover’s the most important part of the album,” according to one of his first biographers, Anthony Scaduto.

That same year Mr. Dylan posed for Richard Avedon. Wearing a checked shirt and well-worn jeans — and with a beaten-up guitar case as a prop — he stood not far from the East River, gazing into the camera lens, an inscrutable half smile on his face. A gelatin silver print of that portrait sold at auction for $62,500 in 2014.

In 1965, a much different Mr. Dylan stood on a rainy Fifth Avenue sidewalk along Central Park as Mr. Avedon shot him for Harper’s Bazaar. Dressed in a black belted overcoat and pointed boots, the singer was now fashionable, wild-haired, androgynous. The dark circles under his eyes said he was no longer the new kid in town, no longer an innocent.

He was also an enthusiastic subject for the photographer and film director Jerry Schatzberg, whose blurred image of an intense Mr. Dylan became the cover of the 1966 album “Blonde on Blonde.” Over a two and a half year period, the two of them came up with enough portraits to fill the more than 250 pages of “Dylan by Schatzberg,” a coffee-table book published in 2018. “You just point the camera at him and things happen,” Mr. Schatzberg said in the book.

The portraits of the mature Dylan for the Céline campaign were shot by Hedi Slimane, the brand’s creative director. Before taking that job in 2018, Mr. Slimane, who designed collections for Yves Saint Laurent and Dior Homme earlier in his career, spent over a year concentrating on photography. He favors stern black-and-white images, and musicians are among his favorite subjects. Others who have posed for him include Kim Gordon, Joan Jett, Joni Mitchell, Lady Gaga, Iggy Pop, Keith Richards, Jack White and Amy Winehouse.

Although he comes from a time when musicians risked being called sellouts for endorsing products, Mr. Dylan has had seemingly no compunction about lending his image and songs to advertisements for Apple, Pepsi, Cadillac, Airbnb, IBM and several other corporations. Perhaps most memorably, he appeared, along with the model Adriana Lima, in a 30-second TV commercial for Victoria’s Secret in 2004. That appearance seemed to make good on something he said during a 1965 news conference. “If you were going to sell out to a commercial interest, which one would you choose?” one of the many reporters in the room asked him. “Ladies’ garments,” Mr. Dylan replied.

Mr. Slimane photographed Mr. Dylan in Los Angeles in December. In one portrait, the 81-year-old Nobel laureate is shown with an acoustic guitar. In another, he is playing a Gibson electric. For fans who have seen him on his recent concert tours, the sight of him with those instruments was noteworthy: His main weapon of choice of late has been the piano or organ. “Dylan’s been 99.9 percent keyboard-based for 20 years now, but he actually did pull a guitar out a few times not too long ago,” Ray Padgett, who chronicles his live performances in the Substack newsletter “Flagging Down the Double E’s,” wrote in an email.

Like the images shot in the ’60s by Mr. Avedon, Mr. Hunstein and Mr. Schatzberg, Mr. Slimane’s portraits allow Mr. Dylan to hang on to his essential enigmatic quality. Wearing a Céline leather jacket that catches the light, his eyes hidden behind dark sunglasses, his expression neutral, he seems to give nothing away. The one thing he can’t hide is his ease in front of the camera.