The Playbook For The Modern Man

The Best Boat & Deck Shoe Brands For The Man Heading To Sea

Don your boat shoes and raise the sails.

Boat shoes have been an essential piece of footwear for mariners since 1935, when a certain Paul Sperry noticed how easily his dog was running around his vessel without slipping or sliding. This led him to cut holes into the rubber soles of his boots, and there and then the boat shoe was born, with Sperry himself developing the first commercial range on the market.

The trend quickly gained traction and brands across America and Europe started producing the in-demand design for casual sailors and yachtsmen. Worn without socks, with a high cut pair of chinos, jeans or shorts with polo shirt, a tried and tested ensemble that stands to this day, they’re an essential part of that classy summer look, even when you’re on dry land.

A typical boat shoe should be super comfortable, with a cushioned yet grippy sole and leather upper, along with 360° lacing. Even though the design has pretty much stayed the same since those early days, there’s a whole heap of materials and price brackets to consider when buying your ideal pair. To make things that little bit easier, we’ve looked at the best 14 models on the market today, to help you look the part next time you’re strolling around the harbour.


Allbirds shoes have quickly taken over the world thanks to their no-fuss approach to design and their sustainability. The brand has quickly become the go-to for the start-up community and surprisingly a few boaties. Their deck shoe is a simplified water-resistant essential that comes in a variety of colours.

Allbirds Tree Skipper $95

Helly Hansen

Helly Hansen is easily one of the most recognisable brands when it comes to navigating the world’s waters, and their range of everything from jackets and mid-layers to accessories and shoes ooze efficiency, style and practicality. These Sandhaven Deckshoes combine suede leather and canvas to create an elegant design that looks as good on the boat as on the pier, with a classic cut upper and an altogether more modern looking sole.

Helly Hansen Sandhaven Deckshoe
Helly Hansen Sandhaven Deckshoe $87


Since setting out in 1983 Nautica has been pretty straight up with their manifesto – to be the world’s leading water-inspired lifestyle brand. What the New Yorkers have managed to create with their Deckloom design is to create an entirely new looking boat shoe for the modern mariner. It’s designed with all the casual style of a pair of sneakers, but with the added advantage of keeping you on your feet whilst riding the swell thanks to a rubber outsole. It also features a J Class lace base and is one of the most competitively priced shoes on this list.

Nautica Deckloom
Nautica Deckloom $90

Kenneth Cole

Legendary New York shoemaker Kenneth Cole may have made his name with women’s footwear in the 80s, but since then he has cast his net much wider, and not only that, he has moved with the times. These Indy Boat Shoes aren’t just the perfect crossover between a classic boat and casual dress shoe, but they’re made with vegan suede for the more eco-conscious client. A clean white sole grips effortlessly to the deck when sailing, or sits comfortably underfoot when meandering small-town streets mid-voyage.

Kenneth Cole Indy Vegan Suede Boat Shoe
Kenneth Cole Indy Vegan Suede Boat Shoe $90


Sperry is the real original when it comes to ocean footwear. Their Authentic Original Boat shoe is great value and exactly how we imagine a boat shoe to look. Its leather upper sits over a Latex rubber outsole for increased cushioning and flexibility, whilst a Razor Cut Wave-Siping maximises traction, to keep you moving around the deck with total ease. A straight-up classic.

Sperry Men's Authentic Original Boat Shoe
Sperry Men’s Authentic Original Boat Shoe $95


Rockport may be a well-established brand around the world these days, but their beginnings are much more humble, starting out as a small family business providing casual dress shoes in 1971. Their Perth Boat Shoe an ode to these beginnings, a perfect blend of style and comfort that appeals to the casual wearer. They’re made from full-grade leather suede which makes them easy to clean over time, with a rubber outsole for longer, more durable grip. They also feature handy polyurethane cushioning that absorbs moisture whilst combating odour.

Rockport Men's Perth Boat Shoe
Rockport Men’s Perth Boat Shoe $110


Sebago is yet another shoe brand to come out of the US state of Maine. They’ve been around since 1946 and specialise in high quality, sewn shoes. Their designs are made for that easy all-day comfort like these Portland Crazy Horse boat slip ons. They’re classic in their style with 360° rawhide lacing and feature a full rubber sole with moc shaped toe. If you’re looking for something that feels great on or off the boat, you certainly get your money’s worth with Sebago.

Sebago Portland Crazy Horse
Sebago Portland Crazy Horse $125

GH Bass & Co

One of America’s stand out heritage shoe brands, GH Bass & Co has been creating quality footwear for generations since 1876. Their Jetty Boat Shoe is perfect for those sunny days preparing your next catch. Hand-stitched seams with waxed threads offer moisture resistance, whilst a rubber outsole keeps you stable on your feet during those rocky moments. Their classic look means they’re perfect when worn with a stylish pair of summer shorts and a polo shirt making you look and feel the part.

GH Bass & Co Jetty Boat Shoe
GH Bass & Co Jetty Boat Shoe $130


American footwear brand Quoddy are renowned for their traditional production methods that have been perfected by generations of shoemakers in the midwest state of Maine. Their Downeast Suede Deck shoes are a picture of seaside comfort, with a suede leather combined upper with silvertone metal eyelets. It’s one of those designs that seem fit for any age or era and fits as well alongside smart-casual summer wear, or more rugged shirt and jeans for that autumnal look.

Quoddy Downeast Suede Deck Shoes
Quoddy Downeast Suede Deck Shoes $160


When a clued up Norwegian entrepreneur realised that his grandfather’s old goloshes were perfect for those rainy days in the city, he laid the foundations for SWIM. Now the brand is home to a huge range of water-friendly loafers that also come in handy if your fold of sailing and fishing. Their Braided Lace Loafer is made with a breathable, waterproof Moulded TPU thread fabric that keeps your feet comfy and odour free. They also feature a nice gripped rubber sole and white braided lacing as if to add to the nautical theme.

SWIMS Braided Lace Loafer
SWIMS Braided Lace Loafer $160


Closely associated with shooting and equestrian sports, British brand Musto knows a thing or two about outdoor apparel made to serve a purpose. Their Nautic Drift shoes are a modern take on footwear for the high seas, meaning they are both practical and highly efficient. They’re made with open mesh quarters that enhance airflow through the shoe for optimum freshness, whilst rapidly enhancing drying times. They also feature a GripDeck sole, which provides excellent 360° traction on slippery decks and surfaces.

Musto Nautic Drift
Musto Nautic Drift $175


Nathan Schwarz founded Timberland back in 1952, and we all know them for their iconic winter boots that help create an altogether more rugged look. But they are much more than that, as highlighted by these impeccable Classic Boat Shoes that first came to market in 1979. A Handsewn, smooth premium leather creates optimum comfort, whilst a Poron Foam midsole and EVA insert provide soft, cushioned resistance whilst on the move. They’re also finished off with 360° rawhide lacing to offer optimum stability when out of the ocean’s swell.

Timberland Classic Boat ShoeMedium Blue Full Grain
Timberland Classic Boat ShoeMedium Blue Full Grain $179


Taking their inspiration from the calm seas of the Mediterranean, Dutch brand Aurelian is all about that laid back approach to design. Their products are slightly higher in the price range, such as these Light Blue Suede Yacht Loafers. They’re made in Italy from wonderfully soft calf suede for bare foot comfort, with ivory coloured soles for that classic boat shoe look. They also work great with a pair of white trousers and a short-sleeved shirt for that European summer evening ensemble.

Aurelien Light Blue Suede Yacht Loafer
Aurelien Light Blue Suede Yacht Loafer $260


If the devil does indeed wear Prada then he must be some snazzy dude and also be fond of the odd boat trip, at least that’s what these Black Leather Boat shoes from the Milano brand suggest. Hand made in Italy they’ve been constructed using a beautiful, smooth brushed leather that sits of a non-marked rubber sole, they’re lade to worn with dress shorts and a summer short sleeve shirt. They may be in the higher price bracket but what you’re getting here is design perfection from one of the world’s most prestigious fashion houses.

Prada Colour-Block Leather Boat Shoes
Prada Colour-Block Leather Boat Shoes $690

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