Tim Little is talking through the moment in 1997 he quit his job in advertising to start his own shoemaking business. An industry, he admits, of which he had no experience. “I remember handing over the keys to my Porsche and the next day walking from my house to Chiswick to buy stationary at WH Smith,” he explains. “I went from director of an agency to absolutely nothing. But then again, aren’t all the best passions irrational?”

 

Well, maybe not so irrational. The decision wasn’t so much taken on a whim but because he sensed an opportunity. He loved the great Northamptonshire shoe marques and their traditional approach to craftmanship, but thought that many of their designs were similarly stuck in the past. His customers clearly agreed, and it wasn’t long before his small King’s Road store in West London was stocking not only Selfridges in the capital, but Barneys in New York. Fast forward another eight years, and he’d made such a name for himself that Grenson, one of Britain’s most famous labels founded in 1866, asked Tim to revitalise its business as creative director. “In 2005 when I started its average customer was probably 50,” he says. “But many were 70 or 80. Its rivals were elite and snobby, too. I thought it was all wrong.”

 

So Tim set to work, using his early experiences with the label as a blueprint. “My first pair of shoes were actually Grensons. They were black toe cap oxfords with five eyelets – the classic City business shoe. My dad told me to keep it simple because then nobody would ever criticise you in an interview. I was 18 and it was the 1980s. But I picked the Grenson because its variant had a chiseled toe rather than being round and frumpy like other manufacturers. It was a bit different. A bit more elegant.” 

 

Today that ethos is all over the business, which has grown to be 100 staff strong and now has five of its own stores. One of his early hits, for instance, came five years ago when Tim experimented with fixing a white wedge sole, normally seen on workwear boots, onto a wingtip brogue. It became a common sight among thirty somethings in East London. Yet at the same time, all its modern shoes kept Grenson’s super-strong Goodyear welting – a technique pioneered by the label in the 1870s that sees the upper stitched to a leather band, which is then stitched to the sole. “In the 1930s, Grenson’s tagline was just ‘The Good Shoe’ and I thought, ‘That’s what we should be like now.’ Our tone of voice is more honest. We want you to wear our shoes everyday and batter them. And when you do, bring them back and we’ll tidy them up.”

 

It’s been so successful that the previous owner sold the business to Tim in 2010. Grenson now has its own store in Manhattan and even provides shoes for the Red Arrows, reestablishing a link that existed decades ago. Their pilots wear Grensons when they attend events or collect medals.

 

But why shoes? Why was the appeal so strong that Tim would gamble everything on them? “Because you invest in them. Like denim, they shape to you the more you wear them.”

 

“In five years time you’ll say, ‘That’s my favourite pair – don’t you dare throw them away.’”