The Best Deck Shoes

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Deck shoes

Dune London Brightling wedge sole suede penny loafer, £80, buy on dunelondon.com

While they’re now a preppy staple, the deck shoe dates back to the ’30s when businessman and fanatical sailor Paul Sperry discovered the hard way just how treacherous painted surfaces could be to stand on when he slipped from his boat into Long Island Sound. Sperry’s non-slip sole was inspired by the groove pattern on his dog’s paws, which enabled it to run on ice, and is just as effective on deck as it is pool side.

Today, the deck or boat shoe has become a style icon both on and off the Isle of Wight, but let’s get one thing clear – leave the socks in the sock draw.

Our roundup of the best contemporary models have plenty of options in brown (the most common colour for deck shoes), as well as black, blue and a funky stripe pattern if you’re looking for a break from the norm. Our picks start at £28 with the faux suede boat shoes from Asos and there are styles from M&S, Toms, Base London and Ask the Missus around the £50 mark. But don’t buy anything without seriously considering Sperry’s classic Topsider boat shoes.

Limited edition Euros Timberland Icon Classic 2-Eye

Inspired by the flags of Italy, England, Germany, France and Spain, Timberland has launched a limited edition boat shoe to coincide with the European Championships. The shoes feature strong, solid colours such as red, blue, green and white, while the German and Spanish shoes also use a beige tone representing their flags’ yellow elements. £105 (reduced to £63 at time of writing), buy on timberland.co.uk: England, France, Germany, Italy, Spain