The menswear-icon-turned-clothing-designer reveals the secrets of his street-style success.

It happens almost immediately. We’ve just sat down at an outdoor table of Morandi, an Italian restaurant around the corner from where Mr Nick Wooster lives in Manhattan’s West Village. We’re about to order lunch when a passer-by recognises him, does a double take, stops and then reaches for his iPhone to take a picture of Mr Wooster. He doesn’t bat an eyelid – he’s used to it – and anyway, this is how it all started five years ago, long before Instagram and back when street style wasn’t yet a thing.

On 16 January 2010, Mr Wooster, then 49, and men’s fashion director of a New York department store, put on a J.Crew black and white herringbone Harris Tweed jacket, Carpe Diem boots and RRL jodhpurs (yes, jodhpurs) and went to the first day of Milan’s menswear fashion shows. “I just got dressed and went to work,” he says in a matter-of-fact way. That day, two men in the street took his photograph and posted the pictures online. One was Mr Scott Schuman aka The Sartorialist, and the other was Mr Tommy Ton – the two foremost men’s street-style photographers in the world. Overnight, Mr Wooster’s life changed. The pictures went viral. “It was a lottery-winning moment,” he says.

Since then Mr Wooster, now 55, has begun a new life as a menswear icon, with blogs ruminating on what he’s wearing, his tattoos and how he’s chosen to style the grey hair on his head or the white whiskers on his face. He helped to pioneer the popularity of the beard, the hipster moustache, tattoo sleeves and the pompadour quiff. “Actually, I have to credit Paul Burros, my barber from when I lived in LA, with that,” says Mr Wooster. “It was he who first suggested back in 2008 that I grow out my crew cut and try a beard and handlebar moustache.”