NOWADAYS, it’s a no-brainer that box-office stars make unbeatable ambassadors for fashion brands. It wasn’t always that way. In the mid-’90s, when cell phones were good for phone calls and not much else, actors would show up for premieres but rarely for fashion shows and never in an ad campaign.

At the time, magazines were fat with glossy ads full of models with impossible faces and bodies photographed in exotic locations mere mortals could never hope to visit. Clothes were sexed up and splashy. Real life was nowhere. That was the game. But Prada wasn’t playing.

Instead of shouting for attention, the Milanese brand quietly nudged its way into the men’s-fashion consciousness with clothes that were simple, wearable, modern and, above all, cool. More of a grown-up uniform than a way of life.

John Malkovich for Prada, 1995

As if to underline it, when Prada produced its first ad campaign in the spring of 1995 for its fall men’s collection, it chose an unlikely avatar: actor John Malkovich. Then 41, Malkovich was Hollywood famous (Dangerous Liaisons, The Sheltering Sky, Empire of the Sun) but had a reputation for embracing varied and unusual roles. He was not the first guy you’d think of for a fashion campaign.

But Malkovich gave Prada’s clothes a different kind of sex appeal. Shot in black-and-white against a stark white background by superstar photographer Peter Lindbergh, Malkovich wore a nylon bomber, a peacoat with a crewneck sweater, a heavy herringbone wool coat and a satin suit, personifying the Prada man while looking like he’d just stepped off the street. It was anti-fashion as fashion. Prada’s campaign gave its clothing instant gravitas, and more unlikely avatars — Tim Roth, Willem Dafoe, Tobey Maguire, Benicio Del Toro — followed in Malkovich’s footsteps.

It wasn’t just on the page, either. In January 2012, Prada’s landmark fall/winter show featured a multigenerational cast of famous yet unconventional actors, including Gary Oldman, Adrien Brody, Jamie Bell, Tim Roth, Garrett Hedlund, Dafoe and Emile Hirsch. At the dawn of the Instagram age, as an expression of Hollywood cool in fashion, it was a high-water mark. It hasn’t yet been matched.

Fast-forward a full 30 years from that first campaign and Prada remains deftly balanced between global popularity and niche coolness. Much of that is derived from the duality of the brand. To some it’s white-hot. To others it signals insider cool. It just depends on how you come at it.

For devotees of the more wearable end of things, there’s a space you need to know about at Prada’s New York men’s store on Fifth Avenue. Tucked away on the second floor, past a pair of sliding green doors, is a room where customers can order suits, shirts, overcoats, knitwear and even leather and shearling, all of it made-to-measure or made-to-order with near-endless permutations of cloths, colours and trimmings.

Classic made-to-measure is often just that: a bit heavy on the classics. Prada, however, offers modern silhouettes that are recognisably Prada in demeanour, from trim three-button suits and crisp cotton dress shirts to heavy denim jeans and luxurious cashmere overcoats, all while seasonally updating colours and cloths. It’s the perfect way to create your own version of the wearable cool that Malkovich personified all those years ago.


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