When Renzo Rosso first tried to sell his jeans, he found a lot of people looked at him as though he was mad. It wasn’t just the price he was asking – $100 at a time when jeans were a commodity item selling for a third of that – but the fact that, well, his jeans were full of holes. And, what’s more, rips, fades and scuffs he had deliberately put there using Black & Decker tools. No wonder some sent them back, assuming they were faulty.

“I just found old and old-looking jeans more interesting than new ones, much as an old house tends to be more interesting than a new one – it’s alive,” says Rosso, who claims to only ever wear jeans. “But at the start people didn’t understand the concept, not the price nor the look. People said I was crazy. But you can get people to trust you if you’re convinced yourself.”

Indeed, this conviction worked out rather well, to the tune of Rosso’s now estimated $3.3bn net worth. Rosso would parlay his idea of pre-distressed denim into the global enterprise that is Diesel, arguably one of the most progressive names in the fashion business of the last three decades and certainly central to denim becoming the industry’s bedrock.

“It’s funny now but just not that many people were interested in denim then,” recalls Rosso of the late 1970s. “You’d go to a big city like London and speak about denim and people would think that you were strange, or trying to do something revolutionary. But I just wanted denim to be more part of fashion. In that, I was part of a small movement. There was no sense that denim would come to be considered a luxury product, or seen on the red carpet.”

But Rosso – who, using his mother’s sewing machine, made his first pair of jeans aged 15, then a few more pairs to sell to his friends – clearly had an eye for opportunity. After studying textiles and working with Adriano Goldschmied’s Genius Group from 1978 – the company that created brands such as Katharine Hamnett Denim and Replay – in 1985, Rosso bought out another of its creations, Diesel.

Rosso quadrupled the fledgling brand’s revenue to create a multi-million dollar company in the first year under his ownership, in part by making it easier to buy into. He offered retailers the chance to send jeans back if they didn’t sell; he promised, if they just gave him one square metre of floor space, they would make more money with his jeans than anything else. And this they did. What sold the jeans, Rosso argues, is that they looked convincing: Diesel’s policy has always been to distress by hand and wash without chemicals, using just water and pumice. This takes longer – and one irony of pre-distressed denim is that it is labour-intensive and so expensive.

But attitude has also been key. If fashion – then as now – took itself all rather seriously, Rosso’s ground-breaking, multi award-winning advertising was loaded with irony, self-deprecation and downright mockery – especially of other denim brands’ reliance on heritage and bodies beautiful. When Diesel opened its first store in New York, it did so opposite Levi’s flagship. ‘For successful living’ has become Diesel’s heavily sarcastic tag line. A favourite of ad creatives was Diesel’s announcement of its sponsorship of young Polish rock star Joanna Zychowicz. It tickled the press with tidbits of gossip, which was greedily scoffed, released an ad campaign featuring the singer, even recorded an album with EMI and announced a world tour. Then it pulled the rug: Zychowicz was entirely fictional.

“Well, it’s easy to take a curvaceous girl and make people pay attention. But the fact is that you always have to be fresh and cool in this business – and product isn’t enough,” says Rosso, a bearded, blondish mop-haired, slightly hippy 60-year-old who looks not unlike the fifth member of Abba. “Denim was becoming a lifestyle, so I wanted to service a group of people who didn’t want to look strange, but who, so to speak, wanted to be a bit different in the box, to be a community.
I didn’t ever want to tell people what to buy but rather to share a philosophy with them.”

Through the 1990s, Rosso would also predict the steady rise of upmarket denim: he launched Old Glory – a line of highly detailed reproduction jeans, at a similar time to Japanese makers – and turned Diesel into a flexible lifestyle brand. You can now buy Diesel furniture, flooring or pushchairs.

Hats off to Renzo

Russo has never been afraid to challenge style orthodoxies

But Rosso also rapidly expanded his business’s reach beyond Diesel, too. Diesel – youthful, pop cultural, Italian casualwear – would become part of OTB, Rosso’s group, owning Euro chic label Marni, cerebral high fashion brands Viktor & Rolf and Margiela as well as a subsidiary operating licensing deals for the likes of Vivienne Westwood and Marc Jacobs. Being a group, Rosso says, provides security, because it means different fingers are in different pies, but also provides inspiration.

“You get a bigger business in part through working with incredible people who grow your brain, who have a different vision,” says Rosso. “I’m good at finding good people.” This talent has also now given him a company with revenues of around €1.6bn.

“I’m not a designer but an entrepreneur, and I can see where things are going. But what is really important to me is that we do something special, be it the clothes, a window display, an ad campaign. It’s really not that important to me to make big sales,” adds Rosso. “I think that emphasis on making money is misplaced. As a private company, we don’t have to justify the numbers. We don’t have to grow if we don’t want to. Say something like that as a public company and the market will kill you. But the clothing business is about selling dreams. And you can’t do that in the corporate world. I like to come here, enjoy the day, have a nice lunch and go home: and to always work with passion.”

‘Here’ is not, as one might expect, in some Milanese monolith, but rather Breganze, a small town about an hour from Venice. “I love the countryside. And country people are friendlier, more genuine,” he says. “If we moved to Milan it would be easier to hire people, and that was a problem at first. No one wanted to come here. But now people do because the quality of life is better. You get hooked up on unimportant things in a big city. There’s the insistence that everything has to happen now.”

Now can happen elsewhere for all Rosso cares. Not that he isn’t well-informed. Indeed, his decisions are based more on an almost overwhelming flow of information – he reads 200-plus magazines a month, has 100 trend-spotters constantly travelling the globe and reporting in with ideas, and claims to read and reply to emails from employees within 24 hours.

“You know,” he adds, “what I like to do is see how things could be rather than how they are. There’s no genius in that, but you do need to give people the opportunity to think with the same spirit. All my life I’ve wanted to do things bigger. And all the time I expected it to get harder as we got bigger. But actually it’s precisely that spirit that has allowed us to get bigger in the first place.”

Add more denim to your wardrobe at diesel.com