The Best Sailing Shoes For The 2024 Season

The Best Sailing Shoes | Life of Sailing

Last Updated by

Daniel Wade

January 2, 2024

The best sailing shoes are both waterproof and slip-resistant. Outdoor boots are popular, but specialty sailing shoes are available.

Traditional sailing shoes are typically made of suede or similar material and feature a low-profile design and relatively flat soles. Modern sailing shoes are designed for offshore use and made of waterproof synthetic material.

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Types of Sailing Shoes

Sailing shoes come in two primary types. These are stylish traditional sailing shoes (which are made of natural materials) and modern waterproof offshore sailing shoes. Both are practical and useful aboard sailboats.

Traditional Sailing Shoes

Traditional sailing shoes have been around for almost a century. These shoes, also known as "yacht shoes," are made from suede leather and are soft and flexible. They're not usually waterproof, but they can be made more water-resistant using chemical treatments.

Traditional sailing shoes are primarily used as a style statement, but they can be quite practical for some sailors. After all, they were designed to be used on boats. They utilize a flat sole that features a unique non-slip texture, which was designed to give sailors traction on a wet deck.

Modern Waterproof Sailing Shoes

Modern waterproof sailing shoes are made from synthetic materials and engineered for traction on wet surfaces. These shoes are preferred by offshore sailing crews who need to stay warm and dry in rough weather conditions.

Sailing Boots

Sailing boots are often used in conjunction with full-body foul weather gear. These boots resemble snow or rain boots, and they're made of a waterproof material such as rubber.

Sailing boots are often reserved for foul weather, as they're heavier and more clumsy than modern lightweight sailing shoes. That said, every offshore sailor should have a set of waterproof boots onboard.

Best Traditional Sailing Shoes

Traditional sailing shoes are practical, stylish, and still widely available. High-quality examples can last for years, and they're a staple of yacht clubs and sailing organizations across the country. Here are four of the best traditional sailboat shoes.

1. Sperry Leeward Boat Shoe 

Sperry practically invented the 20th-century boat shoe, and they're still the go-to shoe company for sailors across the world. The Sperry Leeward Boat Shoe is an excellent introduction to traditional boat shoes.

Sperry's traditional Leeward shoe is a tan leather slip-on deck shoe made of a water-resistant hide. It features a rubber sole, which incorporates the Sperry anti-slip design that's popular across the line.

The design of the shoe is simple, and it's stitched together using thick and sturdy thread for long service life. Its water-resistant treatment makes it easy to clean and quick to dry should it become waterlogged.

This traditional marine shoe is both comfortable and stylish, making it ideal for regattas and dockside events. Despite its looks, the Sperry Leeward shoe is also practical. The Sperry Top-Deck line is popular with sailors and boat owners, as it stands up well to spray and slippery conditions.

2. L.L. Bean Casco Bay Boat Mocs

L.L. Bean is another household name in traditional boat shoes. While not as ubiquitous as Sperry, L.L. Bean shoes are an excellent choice for traditional sailing footwear.

L.L. Bean Casco Bay Boat Mocs are made in the traditional boat shoe style. They're slip-on by design and feature a low-profile sole with a very slight heel. L.L. Bean uses a different sole design philosophy, opting for a non-textured material.

Counterintuitively, the L.L. Bean flat non-textured sole actually has excellent anti-slip characteristics. It's made of sturdy leather that resists sliding on wet decks, and it features slight outsole siphons to increase grip on wet surfaces.

The L.L. Bean Casco Bay Boat shoe is constructed with durable yet flexible leather that is comfortable and easy to clean. It features a leather liner inside, which works well with short socks and wears evenly over time.

That said, the leather liner is designed to work with or without socks. This is a plus, as it makes taking the shoe on and off easy after a day on the beach or walking around the deck barefoot.

These shoes feature a lace-up top with leather laces. They can be tied and left in place, as this is a slip-on shoe. The L.L. Bean Casco Bay shoe can be worn with or without socks, just like the Sperry mentioned above.

3. J. Crew Classic Leather Boat Shoes

J. Crew produces an affordable and classic-looking set of boat shoes that are ideal for a first set. These shoes are made of suede-like leather, and they feature a non-slip rubber sole with a traditional profile.

J. Crew Classic Leather sailing shoes follow the stylistic trends of early boat shoes, yet they incorporate some modern materials that make them more practical for use on a sailboat. These include a non-marking rubber sole that's specifically designed to improve traction on wet and dry surfaces.

These J. Crew boat shoes feature leather laces in a way similar to the L.L. Bean Casco Bay shoe. Like the L.L. Bean variants, these shoes can be worn with or without socks.

The leather is treated for easy cleaning, and they're hand-stitched for strength and longevity. The laces come through the sides of the shoe through grommets, which helps prevent the leather from wearing or breaking around the entry and exit points.

These classic boat shoes are a perfect first pair, and they're affordable enough to wear frequently. They also function as sailboat shoes, which is a plus as many new "boat shoes" are designed for looks only.

4. Sperry Gold Cup Original Boat Shoe

Sperry Gold Cup boat shoes are a classic and premium boat shoe. It features the standard Sperry anti-slip sole and durable leather construction for long life and easy cleaning.

Like most standard Sperry shoes, the Gold Cup Original series is designed to be used on a sailboat or yacht. The shoe's design is based on the original Sperry, which was worn by sailors and yacht owners for decades.

Sperry shoe soles are lightly scored and made with a coarse rubber material that resists slip on wet decks. They're excellent for teak and fiberglass decks and add a layer of security to existing non-slip surfaces.

The shoes themselves follow the classic Sperry design philosophy. They're made from a non-suede leather that's water-resistant and dries out quickly, and they feature leather laces fed through 18k gold plated eyelets.

These shoes feature durable stitching that's used to extend their service life. Inside the shoe, a lambskin lining makes it comfortable to wear with or without socks. The Sperry Gold Cup shoe is a high-quality sailing shoe that's ideal for warm conditions.

Best Modern Sailing Shoes

Although modern sailing shoes lack the aesthetic appeal of traditional sailing shoes, they offer the added convenience of modern design and the functionality of synthetic materials. Here are four of the best modern shoes for sailing.

1. Atlantic Heritage Comfort Boat Shoe

The Atlantic Heritage Comfort Boat Shoe combines traditional styling with modern functionality. It features a suede and stitched appearance and the design of a modern running shoe, and it offers superior support and anti-slip characteristics.

The primary drawback of flat-soled shoes is that they can be uncomfortable, especially if you have foot, back, or knee problems. The Atlantic Heritage shoe eliminates these issues, as it offers the support of a modern shoe.

The primary selling point of the Atlantic Heritage shoe is comfort. It's designed specifically to offer all-day comfort when standing on the deck or walking alongshore. They work just as well on sand and gravel, and they offer elevation in all the right places.

The Atlantic Heritage shoe features a proprietary anti-slip sole, which is designed to provide traction without leaving marks. They stand up to water well, despite the fact that they're not technically waterproof.

2. DLGJPA Lightweight Aqua Water Shoes

The DLGJPA Lightweight Aqua Water shoe series is a radical departure from what most people would consider a traditional boat shoe. These woven shoes are designed for grip and use in wet conditions.

The Aqua Water shoe series takes a different approach to water resistance. Instead of keeping water out, they're designed to let it flow around and inside of the shoe. The woven body of the shoe dries almost as quickly as it gets wet.

The Aqua Water shoe is a warm-weather shoe designed for wet tropical environments and water sports. They're especially useful for launching boats if you need to get in the water to guide the vessel.

The bottom of the Aqua Water shoe is perforated for quick draining. These shoes are highly breathable and ultralight, making them a comfortable and non-slip option for warm weather sailing. 

3. Riomar Deck Driver Stingray Boat Shoe

Are you looking for traditional styling with a modern non-slip grip? The Riomar Deck Driver Stingray is the perfect combination of style and modern materials for use in wet and dry sailing conditions.

A unique feature of the Riomar Deck Driver is the sole. It features a series of protruding rubber buttons that conform to the shape of the ground for optimal grip.

These shoes are non-marking, which is especially important for boats with polished white fiberglass deck spaces. The shoes are flexible and comfortable and designed to be worn with or without socks.

Riomar is a well-known producer of marine shoes, and the Deck Driver Stingray is the culmination of years of experience making high-quality sailboat shoes. These shoes are ideal if you're looking for an attractive and practical modern sailing shoe.

4. Swims Waterproof Penny Loafer

Here's a unique and modern machine-washable sailing shoe designed for comfort and good looks. The Swims Penny Loafer is a well-executed take on an old design and an excellent choice for warm-weather sailing.

The Swims Penny Loafer is completely waterproof and designed for use in wet conditions. It's washable and contains antimicrobial materials to stay sanitary even in the worst conditions.

The shoe features a proven traction sole design with scoring and anti-slip compounds. It's ideal for walking around fiberglass or wooden deck and maintains traction when the deck is wet. 

These shoes are designed to look like penny loafers, which means they're both stylish and comfortable. They can be worn with or without socks, but they're designed primarily for sockless use.

Swims Waterproof Penny Loafer sailboat shoes are currently available in light blue, gray, brown, black, and dark blue. Two-tone gray and neon green are available, and the rest of the colors feature a close-to-matching sole.

Best Sailboat Boots for Rough Weather

Warm weather and calm conditions aren't the only things that sailors encounter. Thus, it's a good idea to have a set of waterproof sailing boots to accompany your foul weather gear. Here are the three best sailboat boots for less-than-ideal sailing conditions.

1. Xtratuf 6 in Ankle Deck Boots

These modern deck boots are the perfect way to prepare for rough weather onboard a sailboat. They're comfortable and waterproof and slip on easily without any laces.

The lack of laces on these boots is more than just convenience. Laces pose a hazard on a sailboat, as it's easy to get them snagged on a cleat or trip while walking around the deck. The Xtratuf 6 Ankle Deck Boots eliminate this hazard.

Aesthetically, these are attractive boots that go well with foul-weather gear. They're not noticeably larger than standard fishing boots. In fact, they're lower-profile than most foul weather boots. That makes them an excellent choice for fair and inclement weather

These are low boots, as they only reach about halfway up the ankle. They're made of a waterproof rubber material that's comfortable, durable, and easy to clean. Xtratuf sailing boots also feature a flat non-slip sole for traction when moving about the deck.

2. Gill Short Cruising Boots

Here's a traditional sailboat boot that's designed for comfort, safety, and water resistance. These "short" boots are fairly tall and ideal for pairing with the waterproof pants from your foul weather gear.

Gill Short Cruising Boots are designed specifically for marine use, which makes them ideal for keeping aboard a sailboat. The soles feature a proprietary design that offers durability and superior anti-slip properties.

These boots resemble traditional fishing boots or barn muck boots, but they're designed for waterproof use on slippery surfaces such as the deck of a sailboat.

They're comfortable and easy to clean, and they're a highly affordable option if you don't already have a pair of foul weather waterproof sailing boots.

3. Rugged Shark Great White Deck Boots

Rugged Shark is a household name in sailboat boots, and they produce a line of premium deck boots for foul weather use. These full-size boots are perfect for all sailing weather conditions.

The Rugged Shark Great White deck boot is a serious heavy-duty deck boot. It's the "real deal," as they say, and this boot offers numerous advantages when the weather gets hazardous (or simply damp and uncomfortable).

These boots are roomy and waterproof, allowing sailors to wear warm insulated socks inside without fear of waterlogging. They work well with standard foul weather gear, and they're high enough to keep water out if the cockpit fills up.

These boots feature an anti-slip sole with corrugated scoring. This anti-slip surface is comparable to traditional deck shoes that date back almost a century. These are proven premium boots with the right combination of durability and flexibility.

The Best Sailing Shoes For The 2024 Season
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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