Magazine covers are tricky things to get right. A mix of attention-seeking and alchemy, the best are startling, provocative and beautiful. This was something that George Lois, art director of US Esquire from 1962 to 1972, understood brilliantly. Lois was a legend, not only as an art director, but as an advertising genius. He was responsible for the “I want my MTV” ad campaign, which revived the fortunes of the music channel, and it was he who coined the phrase “Lean Cuisine” for a food manufacturer.

But the result of his decade at the men’s magazine was a series of 92 iconic covers that featured some of the best known faces of the era photographed in provocative poses by the best photographers. There was Muhammad Ali as St Sebastian; Andy Warhol drowning in a tin of Campbell’s tomato soup; Roy Cohn, Senator Joseph McCarthy’s second-in-command, as a saint; and Marcello Mastroianni saying, “Benvenuto nella bella Italia!” (Welcome to beautiful Italy) on the cover of a travel special in which he selflessly gave Barbra Streisand a tour of his native country.

The covers aren’t just covers. Works of art in their own right, they are currently the subject of an exhibition at the Museum of Modern Art in New York. They were a high point in the magazine’s history, and one that Jeremy Langmead, editor of British Esquire, decided to re-interpret with a twist, in celebration of its 75th birthday.

The premise was simple: he asked the cream of the fashion world to pick a vintage cover and then star in it themselves. He and his team trawled the archives to find a selection for each designer to choose from and, in the end, 11 – nearly all of those asked – agreed to take part, including Miuccia Prada, Giorgio Armani, Vivienne Westwood and Tommy Hilfiger.

“Muhammad Ali was quite a popular choice, but it was first come first served,” says Langmead, who was pleasantly surprised at how smoothly the whole project went off. “John Galliano loved that one straight away, which we kind of thought he would. I think it was popular because Ali was the most famous, and [re-creating] it needed someone who didn’t mind taking their top off, which John, having a good body, was fine with.”

Galliano, who took as his inspiration a matador whom he once saw preparing for a fight, endured six hours of hair and make-up for the shoot, although the photo itself took less than one. Langmead says he loves the end result because it makes him laugh, but cites the Sir Paul Smith picture as one of his favourites, “because it’s quirky and charming and I like the colours”.

Given the egos involved, it is perhaps surprising that the subjects seemed so willing to send themselves up. Langmead thinks it was a combination of being offered the chance to do something out of the ordinary, and also to show that even fashion designers have a sense of humour and irony. Donatella Versace posing as a saint is a case in point, providing a pert contrast to the often lurid tabloid headlines that have punctuated her career. And, although Karl Lagerfeld took months to respond to Esquire’s initial request, after he’d done so, he turned his photograph round, from concept to finished article, in just 24 hours.

“I think he has quite a good sense of humour,” says Langmead. “He’s being tongue-in-cheek, replacing everyone [in the original photo] with him. He performs many different roles – he’s a photo-grapher, designer, book publisher – so I think this was ironic, yet truthful, based on his role today.”

What went less smoothly was the attempt to get original copies of all the covers. Oddly, Esquire didn’t have copies of all of them in its archives, so Langmead and his team spent hours searching on eBay, even sourcing one copy – the Warhol cover – from a sex shop in Soho. But has the experience made him ponder whether magazine covers are more boring these days?

“You do as much as you can within the commercial constraints of your time. Covers aren’t as wild and crazy, but they’re imaginative in other ways. We have more cover lines now, and they’re a work of art in themselves. But, back then, there weren’t so many magazines and it didn’t cost so much to produce them, so you could be a lot braver.”

All images can be seen in the June issue of Esquire, on sale now

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