Ever since intrepid explorer Paul Sperry dreamt of inventing shoes that would stop him falling off his yacht (first world problems, Paul), boat shoes have been considered one of best examples of function-meets-form footwear.

More than 80 years on, whether you consider the casual style a menswear mainstay or think they’re better off overboard, it’s clear that boat shoes are a classic that won’t sink out of view for a long time to come.

They speak of laid-back Riviera style, but the inspiration for these versatile moc-toed, leather shoes came from the most unlikely of places. “Paul found his inspiration from his dog, Prince, noticing that he didn’t slip on ice,” says Jessica Frost from American brand Sperry Top-Sider, which carries his name. “Turning over his paw, Paul noticed hundreds of small cracks and lines going in all directions and that became the inspiration behind the innovative non-slip sole.”

Sperry did what any enterprising person would have after spotting this; he ran home and got to work, hacking up old pairs of shoes with a knife in a bid to mimic the grooves.

The initial makeshift version of the shoe worked, but with one small hitch – the black soles of the prototype left nasty marks all over the deck of the boat. So Sperry decided to combat this by switching to a white sole and the rest, as they say, is history.

River Island

Today, boat shoes are typified by a number of identifiable features. First and foremost is the main material used on the shoe. “Leather is the most typical material found on a boat shoe,” says Frost. “The more premium the leather, the greater number of different shades will be visible around the toe and heel where the leather has been stretched. Nubuck and suede are also excellent choices, the higher the quality, the richer the nap of the material.”