For a while there in the ‘90s and early 2000s, boat shoes (also known as ‘deck shoes’ or ‘top-siders’) were just about the daggiest things you could put on your feet. They were the ‘dad shoe’. Terminally uncool. A sign that the wearer had more or less given up. Then Prada launched a boat shoe in 2019 and they started appearing on catwalks around the world. Suddenly, boat shoes were cool again, and dads everywhere breathed a sigh of relief.
Today, boat shoes are an essential bit of men’s summer casual gear. You don’t need to own a boat, or even enjoy sailing, to wear them. They still carry that vaguely nautical feeling, and they’re flexible enough to dress up or down. Still, there are a few traps to watch out for... Here’s our ultimate guide to wearing men’s boat shoes.
What is a boat shoe?
Boat shoes are typically constructed from canvas or leather with non-marking rubber soles created for wear while sailing. Every aspect of the shoe is designed with the wear-and-tear of the sailing life in mind. The siping pattern cut into the soles provides much-needed traction on a wet deck; the oil-treated leather construction repels water; and the stitching is highly durable.
Styling boat shoes
Boat shoes are preppy and coastal by nature, so lean into those vibes. Don’t try to ‘edge up’ boat shoes. It won’t work. These guys tend to work best with chino shorts, linen shirts, or loose fitting crew neck tees. Anything beach-y and breezy. Don’t go too crazy with colours or style combinations, either. There’s a reason 90% of boat shoes are navy, brown leather, or white. Those colours are the most versatile, and they tend to suit the style best.
Boat shoes and socks
Unless you’re very brave, or very foolish, don’t wear boat shoes with socks. At least, not visible socks. Boat shoes work best with invisible ankle socks, also known as sock-ettes. You want to be flashing some ankle here. Wearing calf-height crew socks with boat shoes is peak dad behaviour – it’s right up there with thongs and socks. You can also go completely sockless (AKA sock commando) but we don’t recommend it. Not wearing socks will cause blisters and odour, and the sweat will eventually damage your boat shoes’ leather upper.
Consider the cuff
Another boat shoe mistake is allowing your pants to flap around your ankles or, even worse, hang over your boat shoes. Boat shoes work best with chino pants, although jeans can work too. Either way, you need to cuff. We recommend either a simple double or single cuff (you can read our in-depth cuffing guide for more info). Avoid skinny pants or bootcut jeans, too. Boat shoes need a slim or regular fit pant – nothing painted on, and nothing too loose around the calf.
Don’t overdo it on the cuff, either. Some guys wear their boat shoes with jeans that are cuffed so high they look like capris pants. No-one thinks you’re a 19th century sailor, so one or two rolls will do the trick.
How to tie boat shoes
High-quality boat shoes usually come with thick leather laces, which can make tying them up kind of tricky. Leather doesn’t knot easily. You can try a regular bow, but if that keeps coming untied, try a chain knot instead (you can find good step-by-step guides for this one online). Whatever knot you choose, it’s generally a good idea to tuck any loose laces into the side of your boat shoes. Don’t leave them trailing along the ground. Apart from tripping over them, loose laces will also fray and degrade quite quicky.
Smart casual boat shoes
Boat shoes work best with a smart, preppy look. But you can take this thing too far. Pastel shirts, woven belts and big diver watches all scream ‘Frat Bro’, and no-one wants to be that guy. Instead, keep things simple with cuffed tan chinos, a pique polo, navy chino shorts, or maybe a rugby-style top. A few nautical stripes here and there are okay, but again, don’t overdo it. A simple button-down shirt, crew knit, tailored chinos and a pair of HATCH boat shoes are all you need for a smart casual look.
Casual boat shoes
Boat shoes have become one of our favourite casual summer shoes. Right up there with sneakers and sandals. They’re just so versatile. You can wear them down the shops, to the beach, out to lunch, around the house. And all you really need is a pair of SPINNAKER boat shoes (try them in almond suede for something different) some tan shorts and a white crew tee. Throw on some vintage sunnies and you have a great casual look, perfect for the beach or the barbecue. Don't be afraid to go for patterns like gingham, plaid and stripes on top, too.
The history of boat shoes
As the name suggests, the boat shoe was originally designed to be worn by sailors. That all changed in 1935, when a new incarnation of the boat shoe hit the scene inspired by a pet dog. Transfixed by his dog’s ability to maintain traction while running over an icy surface, the designer set out to develop and patent a shoe with wave-like soles for greater grip.
Using a knife, he cut thin slits or ‘siping’ into the soles of his shoes, and the boat shoe as we know it today was born. Sailing enthusiasts and fashion plates alike could purchase a pair of the original boat shoes for $4.50 (USD).
The profile of the boat shoe continued to rise throughout the ’30s, and in 1939 the U.S. Navy negotiated the right to manufacture boat shoes for its sailors. Full mainstream success hit later in the century, when the shoe appeared in the Jaws movie franchise and was declared the official shoe of preppy style by 'The Official Preppy Handbook' in 1980.
The construction of boat shoes
Boat shoes are typically constructed from canvas or leather with non-marking rubber soles, perfect for gripping a yacht’s deck. Every aspect of the shoe is designed with the wear-and-tear of the sailing life in mind. The siping pattern cut into the soles provides much-needed traction on a wet deck; the oil-treated leather construction repels water; and the stitching is highly durable. Even the laces are generally made from leather, for extra longevity in salty conditions.