Kick off long summer weekends with the classic warm weather stable, boat shoes. While they might be part of a more preppy male sense of style, all gentlemen alike can appreciate their comfort when worn in the sunlight. When it comes to boat shoes, these sailing slip-ons pair perfectly with everything from cargo shorts to jeans, khakis and more.

However, you don’t have to be a sailor by heart to sport them. Sure, the traction on boat decks in unbeatable, yet, so is the comfort and style for morning walks spent out by the beach.

It’s a lot like wearing them without or without socks, the choice is entirely yours. With that said, before I get into the top 17 best boat shoes for men below you might be curious to know how this iconic footwear first got it start.

The history

The story dates back to the 1930’s with Paul A. Sperry, a devoted boated and sailor from New Haven, Connecticut. One cold winter morning Sperry watched his dog zip across the ice without so much as slipping a foot.

In the moment he had realized the pads of his pup Prince’s paws formed a herringbone-like pattern with all the grooves and cracks. By cutting a siping pattern into the soles of his own shoes he had managed to unlock the power of a phenomenally strong grip.

Within time, Sperry would share his discovery to the world under the Sperry Top-Sider company. Since then, boating shoes have become a stable in popular coastal area footwear over the years. Now, aside from the siping pattern for secure sea legs on a wet deck, most boat shoes today as feature oiled leather to repel water.

You’ll also find a 360-degree lacing system, typically with rawhide and two or three eyelet, plus a moc-toe construction. Of course, the fashionable styles you’ll find below feature a wide range of variations from the tried and true traditional to the more bold and modern.