“Inclusivity is more part of the conversation than it has ever been before, but it goes far beyond black and white,” Mr. Enninful said. “It is about all creeds, all colors, all sizes and people just living their truths. A lot of this is about digital giving people voices, and a new generation who refuse to compromise and want answers to the questions that matter to them. Given the state of the world we live in, sometimes I think we all feel like we’ve fallen down the rabbit hole. For me, a retelling of ‘Alice’ for the modern world was a perfect project, particularly once the cast fell into place.”

For Mr. Combs, who made headlines in 2001 when he posed with Ms. Campbell for a cover of British Vogue, the calendar comes at a time when there needs to be what he called “an unapologetic expression of black pride.”

“I moved mountains to be a part of this,” said Mr. Combs, as he sat in his dressing room after the shoot. “It is a chance to push social consciousness and break down barriers. For so many years, something like this would not have happened in the fashion world, so it feels like being part of history and playing an active role. I want to lead by example.”

For decades, the Pirelli calendar, first published by the Italian tire company of the same name in 1964, was a soft-core ode to beautiful women. Shot by A-list photographers and usually starring scantily clad supermodels, it is a collector’s item and has never been sold on the open market. Instead, it is given to insiders — a group of establishment opinion makers including celebrities, media professionals, politicians and chief executives, as well as to Pirelli’s most valuable clients and distributors.