Boat Shoes: Perfect For Nautical Adventures And Beyond

Boat shoes are a type of footwear that is designed for boating and maritime activities. They are known for their non-slip rubber soles, which provide traction and stability on wet and slippery boat decks. Boat shoes are typically made from leather or canvas and feature a moccasin-style toe, a 360-degree lacing system, and a quick drainage system to keep feet dry. While they are functional for boating, they have also become a popular fashion choice, offering a casual and stylish look for both men and women. They are commonly worn in warmer weather with shorts, jeans, or trousers and can be paired with or without socks, depending on personal preference.

Boat shoes and their nautical heritage

Boat shoes have become a classic casual shoe trend in the menswear world. But their history is rooted in nautical heritage.

The History of Boat Shoes

The modern boat shoe was invented in the early 1930s by Paul Sperry, an avid sailor who struggled to maintain a firm foothold on the slippery decks of his boat. One winter day, he noticed his dog, Prince, had incredible grip while running across the ice. Upon closer examination, Sperry realised that the natural cracks and grooves on Prince's paws formed a herringbone-like pattern that gave him grip.

The Design

Inspired by his dog's solid performance on the ice, Sperry designed boat shoe soles with a similar pattern. These soles are scored or "siped", which allows the wearer to maintain grip while on slippery surfaces, such as a boat deck. The soles are traditionally white and non-marking to prevent scuffing and damage to boat surfaces. The upper part of the shoe is made from leather or canvas, which can withstand exposure to water, salt, and other elements.

From Boat Decks to Everyday Wear

Boat shoes were originally made for sailors and boaters but it didn't take long for people outside the boating world to notice the perks of these shoes. Today, they are worn by boaters and non-boaters alike, both for functional and aesthetic reasons.

Boat shoes' unique design and construction

Boat shoes are a unique type of footwear designed with sailing functionality in mind. Invented in 1935 by Paul A. Sperry, an avid sailor, the shoes were created to provide extra traction on wet boat decks. Over time, they have become a classic staple for spring, summer, and fall footwear, favoured for their comfort and style versatility. Here are some key aspects of boat shoes' unique design and construction:

Design

Boat shoes typically feature a moccasin-like construction with a low cut, soft, white, non-skid, non-marking, siped rubber sole. The siping, or slits, on the rubber sole, is a defining characteristic that enhances traction and prevents slipping. The soles are also designed to be non-marking, ensuring they don't leave any marks on boat decks.

The upper part of boat shoes is usually made from leather, which is treated with wax or oil to repel water and keep feet dry. The open-top design allows water to escape, ensuring that moisture is not trapped inside the shoe. This design consideration is why boat shoes are typically worn without socks when sailing.

Boat shoes often feature a unique lacing system, with laces extending up the sides and wrapping around the heel. This secure lacing configuration ensures the shoe is held firmly to the foot, accommodating the agility and movement required while sailing. The laces themselves are typically made from leather for added durability and waterproofing.

Construction

Boat shoes are carefully constructed to provide both functionality and style. The leather uppers are treated with wax or oil to create a water-repellent barrier, ensuring that water rolls off the surface. This treatment also helps to maintain the appearance of the shoe over time.

The toe box of a boat shoe is designed with comfort in mind, utilising moccasin-style stitching. This stitching joins the tongue of the shoe to the upper, reducing rubbing and chafing against the toes, making it comfortable for barefoot wear.

The construction of boat shoes prioritises durability, ensuring they can withstand the rigours of sailing while also providing long-lasting style.

Boat shoes' transition from workwear to a fashion staple

Boat shoes were originally designed for sailors and boaters to prevent slipping on boat decks. The practical, non-slip rubber sole and unique hand-sewn upper design soon caught the attention of non-boaters, and the shoes began their transition from workwear to a fashion staple.

The boat shoe's journey from sea to street was aided by its association with preppy styles. In 1980, the publication of *The Official Preppy Handbook* by Lisa Birnbach identified the boat shoe as an essential part of preppy styles. This association was further solidified by the US Navy, which began manufacturing Top-Siders for its sailors in 1939.

Over time, the boat shoe gained manufacturers beyond the Sperry company and fans far outside nautical circles, becoming indelibly linked to a general East Coast preppy look. While some continue to avoid the shoe for this exact association, others have embraced it as a wardrobe staple, pairing it with both casual and dressier outfits.

In recent years, the boat shoe trend has experienced a resurgence, with early co-signs from fashion brands like Miu Miu and JW Anderson. At New York Fashion Week, street style muses have been spotted pairing their boat shoes with slip skirts, baggy trousers, hot pants, and knee-socks. The shoe has also been featured on the spring 2025 runways of fashion powerhouses like Collina Strada and Monse, showcasing its versatility and appeal to the fashion world.

The boat shoe's transition from workwear to a fashion staple can be attributed to its unique design, functionality, and versatility. Its non-slip rubber sole and hand-sewn construction make it a practical choice for maritime activities, travel, and everyday wear. Additionally, its relaxed aesthetic and ability to be dressed up or down make it a versatile option for various occasions, from the beach to the office to a date.

Whether you're a sailor or a fashion enthusiast, the boat shoe has proven its staying power as a classic casual shoe trend that offers both style and comfort.

The dos and don'ts of wearing boat shoes

Boat shoes have become a classic casual shoe trend in the menswear world. Originally made for sailors and boaters to prevent slipping on boat decks, they are now worn by boaters and non-boaters alike. Here are some tips on how to style boat shoes:

The Dos:

• Wear them to the beach or for other maritime activities.
• Wear them when travelling as they are comfortable and easy to get on and off.
• Wear them to the office, as long as the environment is business casual.
• Wear them on a date as a conversation starter.
• Wear them with jeans. For a nautical look, try cuffing the hems of your jeans.
• Wear them with colourful chinos, but make sure the colours contrast to balance the look.
• Wear them with shorts in the summertime. Ensure the shoes are plainer if they are attention-grabbing to avoid overkill.
• Wear no-show socks to keep your comfort without ruining the look.
• Wear them with suits by opting for dark wash denim and a blazer for a business casual twist.

The Don'ts:

• Wear them in the winter as they may get wet and will look out of place.
• Wear them for a fancy occasion as they are meant for more casual and laid-back events.
• Wear them with visible socks as this will make you look like a newbie.
• Wear them with suits as they don't fit this formal look.
• Wear them with preppy-reading clothes unless that is the look you are going for.

Boat shoes' evolution and modern styles

Boat shoes have come a long way since their invention in the 1930s by Paul Sperry, an avid sailor who wanted to address the problem of slippery boat decks. The shoe's practical, non-slip design and unique hand-sewn upper construction initially attracted boaters, but it wasn't long before people outside the nautical world began to adopt them. Over time, boat shoes became a classic casual shoe trend in menswear, embraced by both boaters and non-boaters for functional and aesthetic reasons.

In the 20th century, the deck shoe or boat shoe gained manufacturers beyond the Sperry company and fans far beyond nautical circles, becoming indelibly linked with a general East Coast preppy look. However, some people avoided boat shoes due to this association or because they believed they should only be worn on boats. Despite these criticisms, the boat shoe has endured as a versatile and functional footwear option.

In recent years, the boat shoe has undergone an evolution, with collaborations between Sperry and brands like skate brand Pleasures and golf darlings Malbon. Italian labels have also reinterpreted the style, introducing premium suede versions and new colour palettes. Additionally, the return of preppy fashion has made styling boat shoes feel more feasible, with brands like J.Crew and Rowing Blazers embracing the look.

Today, boat shoes are available in various colours, materials, and finishes, offering something for everyone, from traditional models to updated styles. While leather, specifically nubuck, is most associated with classic boat shoes, other materials such as canvas and suede are also used.

When it comes to styling, boat shoes are versatile and can easily replace sneakers and loafers in everyday wear. They pair well with casual outfits and can be dressed up or down, making them suitable for various occasions. While they should not be worn with formal styles like Oxfords, they can be worn with blazers, unstructured sports coats, and odd jackets to capitalise on their relaxed aesthetic.

In terms of trousers, boat shoes should be paired with tailored (non-cargo) shorts or well-fitted, tapered or straight-leg jeans or chinos. Denim, in particular, is a happy partner to boat shoes, with a classic, straight-leg cut in dark blue denim being a timeless choice. For a more effortless, nautical look, cuffing the hems of jeans can complement the boat shoes and draw attention to them.

While boat shoes were originally designed to be worn without socks, modern styling allows for more flexibility. Socks can be worn with boat shoes, but it's important to coordinate them well with the trousers and shoes. No-show or ankle socks are a good option if you're concerned about bare feet sweating or prefer a more urban look.

Overall, the boat shoe has evolved from its utilitarian origins to become a versatile and fashionable footwear choice, offering both comfort and style for various occasions.

Frequently asked questions