Designed to offer better grip on wet, slippery decks, boat shoes have moved on from their original maritime purpose. Smarter than a trainer and less dressy than a loafer, they bridge the gap that separates casual from formal.
If you are a purist, the Sperry Top-Sider is the most authentic style of all – invented in 1935 by Paul A Sperry, who scored out the soles of his own casual shoes with a knife to stop them slipping on wet surfaces.
The best Top-Sider in my opinion is the two-tone, olive and brown cowhide style with cushioned rubber soles and contrast suede laces.
Docksides is the definitive design from Sebago; the tan suede and chestnut leather bi-colour style is very versatile. For something you can wear with a suit, Timberland’s classic full-grain boat shoe with a moccasin stitched toe is a nod to the traditional penny loafer.
If you mean business, Prada’s contemporary spin on the classic deck style, in tan and black, marries fashion with function. Lacoste has a sportier style in red, white and blue that would look good with a slim-fit chino, and Zara offers one with traditional styling, in four contrasting materials, that benefits from a skate-shoe sole. Perforated fabrics are on trend, too; M&S Collection and Dune have great examples.
Boat shoes should never be teamed with socks and should never have a black sole. White and traditional gum coloured are the most authentic. The more worn in, the better they look.
10 of the best
Perforated boat shoes, £35, M&S Collection (marksandspencer.com)
Classic full-grain boat shoes, £110, Timberland (timberland.co.uk)
Two-tone Dockside boat shoes, £155, Sebago (russellandbromley.co.uk)
Grain-calf Lance boat shoes, £78 (from £195), Grenson (grenson.com)
Nautic supple leather boat shoes, £110, Lacoste (lacoste.com)
Leather boat shoes, £515, Prada (mrporter.com)
Calf leather boat shoes, £320, Church’s (church-footwear.com)
Three-tone deck shoes, £39.99, Zara (zara.com)
Bonavista mesh boat shoes, £60, Dune (dunelondon.com)
Two-tone Top-Sider leather boat shoes, £105, Sperry (mrporter.com)