Looking for the most comfortable boat shoes for sailing? Check out these six styles that focus on support and cushioning to find exactly what you need.

Among the many reasons to own a dedicated shoe for sailing, finding the most comfortable boat shoe should be at or near the top of the list. Whether racing, cruising, or just day sailing, only a proper fit and solid traction supersede the need to comfortably stay in a pair of shoes as long as the day demands.

Above all else, the most comfortable boat shoes provide plenty of cushion and stability. They should be fast-drying without seeming flimsy. And, of course, a non-marking sole with wet-grip traction is a must.

When it comes to the comfort factor, there are a few things to look for straight away. A sneaker-like profile is the first tell. The shoe may still have traditional topsider DNA—with a stitched moccasin toe and two or three eyelets—but the footbed will resemble nothing so much as a running shoe.

This extra bulk is a natural trait of the best boat shoes built with comfort in mind. That’s because they often include cushiony features, such as an EVA foam midsole and ample arch support.

The most comfortable boat shoes will fit snuggly without constricting, an area where slip-on models shine. Their one disadvantage is that if they slip on, they can also slip off, perhaps inadvertently.

Whatever style you prefer, here are six shoes in a wide range of price points to keep you sailing comfortably all day and all season long.

6 of the most comfortable boat shoes for sailors

Most Comfortable Boat Shoes_Chatham Buton

Chatham Buton G2

Specifications | Sizes: 6 through 12 | Colors: Navy, Red Brown, Walnut | Construction: Nubuck leather and mesh

Reasons to Buy:

– Great looking shoe with comfort top of mind.
– Extra cushiony.
– Nice blend of traditional deck shoes with sneaker comfort.

Reasons to Avoid:

– High price point.

One of the tradeoffs in comfortable shoes is that they sometimes appear too bulky. Consider those clunky hospital shoes and orthopedic sneakers.

Chatham’s Buton G2 deck shoe navigates this terrain beautifully with a well-proportioned upper of nubuck leather on a well-padded midsole.

The G2 Collection is Chatham’s premium shoe line, and the Buton G2 is a top-of-the-line offering. Water-resistant leather is paired with mesh side panels to promote breathability and drying.

It emphasizes comfort without straying from a traditional deck-shoe lineage. Chatham’s shock-absorbing sole spring poron technology adds superior cushioning as well as anti-bacterial protection.

When considering any leather boat shoe meant for wet conditions, keep in mind that the leather will stretch. That means a snug fit is just about right when the shoes are new.

Buy from Chatham

Note: We may earn a commission when you buy through links on our site, at no extra cost to you. This doesn’t affect our editorial independence.

Dockers Beacon

Dockers Beacon Boat Shoe

Specifications | Sizes: 7 through 13 (medium width) | Colors: Navy, Gray, Tan, Dark Tan | Construction: Leather and mesh

Reasons to Buy:

– Very affordable.
– Emphasis on comfort.
– Mesh panels for drainage.

Reasons to Avoid:

– Some buyers report they run narrow.

If you are looking for a more affordable deck shoe that nonetheless emphasizes all-day comfort, check out the Beacon Boat Shoe from Dockers. It’s the same moccasin style topsider so familiar to boaters, but with extra stability and support at a bargain price.

The sole is EVA foam, which is a material used in many running shoes for its rebound qualities.

Uppers are made from treated leather to resist stains and shed water. A springy footbed is treated with Cleansport NXT, which is Dockers’ anti-bacterial technology.

Elasticized goring between the upper collar and the tongue makes it easy to slip the shoe on and off without unlacing it. Double goring on both sides of the shoe also accommodates wearers with a high instep by automatically adjusting to the foot shape for a custom fit.

Buy from Amazon
Buy from Belk

Nantucket III

World Wide Sportsman Nantucket III

Specifications | Sizes: 8 through 13 (with limited half sizes) | Colors: Tan Beige | Construction: Nubuck leather and mesh

Reasons to Buy:

– Budget-friendly.
– Slip-on comfort.
– Classic leather and mesh combination.

Reasons to Avoid:

– Available only in beige.

For true slip-on convenience, the World Wide Sportsmen Nantucket III is hard to beat in both price and performance. At less than £35 ($43) the Nantucket III has all the comfort and stability available in many shoes twice the price.

The shoe features nubuck uppers with leather trim and generous mesh panels for ventilation and weight reduction. There are also additional eyelets at the outstep to allow drainage.

A removable high-cushion insole provides shock absorption for long days on the water. The leather-reinforced and well-padded collar offers the kind of fit and stability normally found in lace-up shoes.

If you want a budget-friendly slip-on with plenty of support for sailing, fishing, or pleasure boating, the Nantucket III deserves a good look.

Buy from Cabela’s
Buy from Bass Pro Shops

Most Comfortable Boat Shoes_Sperry Billfish

Sperry 3-Eye Billfish Boat Shoe

Specifications | Sizes: 7 through 15 | Colors: Dark Tan, Tan Beige | Construction: Full-grain leather and mesh.

Reasons to Buy:

– Good value.
– Three rust-proof eyelets for best fit.
– Durable and comfortable.

Reasons to Avoid:

– One of the bulkier deck shoes.
– May feel too warm for tropical climates.

When it comes to the most comfortable boat shoes for men, it’s hard to beat the value and performance found in Sperry’s 3-Eyelet Billfish.

The combination of leather and mesh reduces weight while still providing substantial support over a thick sole with full-length cushioning. Generous padding in the heel and tongue add to the springy feel.

The tread is wave-siped over its entire surface, and the high-grip rubber outsole extends up and around the sides of the foot for optimal traction.

Despite this shoe’s heft, the mesh side panels promote air flow to help keep your feet dry and comfortable all day long.

Buy from Amazon
Buy from Sperry

Most Comfortable Boat Shoes_Sperry Koifish

Sperry Women’s Koifish

Specifications | Sizes: 5 through 12 (medium width) | Colors: Grey, Navy, Tan | Construction: Leather and textile.

Reasons to Buy:

– Extra padding in tongue and insole.
– Traditional deck shoe style.
– Mid-range price.

Reasons to Avoid:

– Fit may run narrow.
– Beware of Sperry imitations online. Caveat emptor!

Unfortunately, there does not seem to be as much market emphasis on comfortable boat shoes for women as there is for men. The category is relegated primarily to topsider styles with a few trainers and sneaker-inspired shoes here and there.

The Sperry Women’s Koifish is designed specifically with comfort in mind. It’s a take on the classic leather topsider with a stitched moccasin toe, but several touches set it apart from traditional deck shoes.

First, the tongue is padded rather than solid leather. There is also extra insole padding in the arch and heel, which is built over an EVA midsole for better shock absorption.

Despite the soft fabric panels, it’s a sturdier shoe on a more forgiving platform than many other two-eyelet deck shoes.

And of course, Sperry’s non-marking rubber outsole with Wave-Siping tread ensures that you will be as sure-footed as you are comfortable.

Buy from Sperry
Buy from Zappos
Buy from Dillard’s

Most Comfortable Boat Shoes_Helly Hansen Newport F1

Helly Hansen Newport F-1 Deck Shoes

Specifications | Sizes: 8 through 11.5 | Colors: Navy | Construction: Leather and mesh

Reasons to Buy:

– Running shoe technology.
– Contemporary style.
– Mid-range price.

Reasons to Avoid:

– Available in only one color.
– Considerable bulk.

The heritage of Helly Hansen’s Newport F-1 deck shoe is easy to spot. It is equal parts classic topsider and modern athletic shoe. Only this sneaker is designed specifically with mariners in mind.

Constructed of waterproof full-grain leather, the upper has a well-padded collar and 3-eyelet wrap-around lacing to offer the most comfortable fit. It sits atop an EVA molded midsole for the rebound and support that active sailors need.

The Newport midsole also features a second layer of firmer EVA foam, called a medial side post, to provide additional support. This feature helps reduce excessive pronation or turning of the ankle.

Mesh side panels keep the weight down and promote breathability, and the non-marking tread features about as much siping as one could fit on a deck shoe. And that’s a good thing!

Buy from Helly Hansen

Didn’t find what you’re looking for? Head to Amazon’s dedicated sailing page for more marine products.