The best men's boat shoes for sailing are designed to meet specific use cases. Here are 6 top sellers that cover the waterfront with both style and substance.

Picking the best men’s boat shoe for your type of sailing doesn’t have to be complicated, but often it is. On one hand, you can go with a basic two-eyelet deck shoe, or topsider, as it is sometimes called. On the other hand, well, everything else.

In sailing footwear, the variety of form, function, and price can be staggering. Options range from bottom-dollar canvas loafers that have all the integrity of cheese cloth, to designer deck shoes that cost more than some chart plotters.

In between are myriad options to choose from. Some ofd the best boat shoes focus on technical performance, while others emphasize style. There are deck shoes specifically built for everything from dinghy racing to offshore passage-making.

No matter your need, it’s important to first define your use-case priorities. A Vendée Globe competitor probably isn’t going to be well served with a pair of discount leather topsiders. Just like a dinghy cruiser doesn’t need a high-dollar racing trainer.

Whatever your sailing category, focus first on fit, traction, and drainage. If your feet are often wet, look past all-leather deck shoes and lean into mesh shoes with synthetic uppers and, preferably, integral drainage.

If you are frequently moving about the deck, such as while crewing on a race boat, stability and traction should be a top consideration.

With these points in mind, here are six highly rated men’s boat shoes that will cover most sailing applications from deck to dock.

6 of the best men’s boat shoes

Chatham Deck II boat shoe

Chatham Deck II G2

Specifications | Sizes: 6 through 15 with some half sizes | Colors: blue, chestnut, chocolate, walnut | Construction: Leather

Reasons to Buy:

– Classic two-eye deck shoe.
– Good shock absorption.
– Lace-up design for fit and stability.

Reasons to Avoid:

– Premium price.
– Doesn’t dry as fast as a synthetic shoe.
– Sizes run large.

When it comes to the traditional two-eye deck shoe, nobody does it better than Chatham. The G2 collection is their top-of-the-line topsider for both men and women and is one of the best boat shoes on the market.

It features waxed walnut leather for water and stain resistance, along with waxed thread and non-corrosive eyelets.

Some of the best moccasin-style men’s boat shoes can feel a little flat-footed. That’s why the Deck II G2 incorporates proprietary cushioning and anti-bacterial insoles for all-day comfort. The shoe also is backed by a 2-year guarantee.

And, of course, the siped rubber sole is just what you need to stay on deck in slippery conditions.

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.

Best Men's Boat Shoe_Sperry Billfish 3 eyelet

Sperry Men’s Billfish 3-Eyelet Boat Shoe

Specifications | Sizes: 8 through 13 | Colors: Tan Beige, Dark Tan | Construction: Leather with mesh panels

Reasons to Buy:

– Affordable price.
– More cushioning than most 2-eye topsiders.
– Good ventilation and drainage.

Reasons to Avoid:

– May be too bulky for warmest climates.
– Some buyers warn of quality control issues

If you need more support than a two-eye shoe but still want the moccasin style, take a look at Sperry’s Billfish boat shoe.

It incorporates an extra eyelet on top of a beefier platform for sneaker-like performance in a grippy, non-marking boat shoe. And it still has the classic moccasin look.

As the name suggests, the Billfish is built with fishermen in mind. But it’s also an excellent choice for sailors who need extra cushioning and stability while moving about on deck.

Despite its bulk, the Billfish keeps weight down by incorporating mesh side panels. This feature also promotes moisture wicking and minimizes foot odor.

The siped rubber sole is cupped around the rand. That means the grippy surface extends up and around the outstep, instep, and heel for better traction on angled or uneven surfaces.

This shoe might feel too beefy for the tropics, but in most temperate climates, it’s a great buy from the inventor of the original deck shoe.

Buy from Sperry

Buy from Amazon

Best Men's Boat Shoe_Tribord 500

Decathlon Tribord Sailing Boat Shoes 500

Specifications | Sizes UK 5.5 through UK 12 | Colors: Dark Chocolate | Construction: Leather

Reasons to Buy:

– Very affordable.
– Traditional topsider style.

Reasons to Avoid:

– Available only in one color.
– Stiffer and not as well made as pricier models.

It is hard to go wrong with a pair of leather topsiders for under £40. While the Tribord 500 might not lead the field in a comparison of the best men’s boat shoes, Decathlon leads the way in affordable water sports gear and apparel with its Tribord sailing brand.

The Tribord 500 boat shoe is a traditional two-eyelet topsider with the same leather uppers and lacing as found on higher-priced brands, but at a greatly reduced price.

These are shoes you can use and abuse for as long as they last and then dispose of or donate without feeling guilty.

If you are seeking ultimate stability, arch support, and performance, perhaps look elsewhere. But if you want a budget-friendly boat shoe that will do what you need without breaking the bank, then look no further.

Buy from Decathlon

Best Men's Boat Shoe_Helly Hansen Skagen

Helly Hansen Skagen F-1 Offshore

Specifications | Sizes: 7 through 13 | Colors: Phantom EBO (white), Racer Blue, Navy | Construction: Mesh upper with EVA midsole.

Reasons to Buy:

– Advanced technical performance.
– Good foot protection.
– Comfort and stability.

Reasons to Avoid:

– High price.

Well known for its high-performance clothing, Helly Hansen makes an equally big splash with technical footwear for boaters. The Skagen F-1 Offshore should be in any discussion of the best men’s boat shoes.

This is a sneaker-style shoe designed with ocean sailors in mind. The synthetic mesh upper is breathable and lightweight, and it is built on a thick, rugged sole for cushioning and foot protection.

The removable EVA insole is treated with antibacterial technology to reduce foot odor and fungi, which will keep you comfortable on long passages.

At first glance one might mistake the Skagen F-1 for a running shoe, except that it features an aggressive non-slip sole designed specifically for working on a wet deck.

It is also one of the best-looking sailing shoes on the market, though at a premium price.

Buy from Helly Hansen

Buy from Amazon

Best Men's Boat Shoe_Musto Dynamic Pro II

Musto Dynamic Pro II Adapt

Specifications | Sizes: 7 through 12 | Colors: Vallarta Blue, True Navy, Musto PLA (white/blue) | Construction: Mesh with TPU overlay

Reasons to Buy:

– Designed for racing.
– TPU welded frame for support.
– Good shock absorption

Reasons to Avoid:

– May be too much shoe for casual sailing.
– Expensive.

Serious racers need a serious shoe, and Musto’s Dynamic Pro II performs from heel to toe and everywhere in between.

The unique lacing system is elasticated to snug the shoe against the top of your foot, ensuring a comfortable custom fit.

A breathable mesh upper promotes drainage and reduces weight. The mesh is reinforced by a thermoplastic polyurethane (TPU) welded overlay to protect and stabilize your foot. That TPU frame also extends over the toe box for extra protection.

The heel and mid-sole are EVA foam, a component long used in running shoes to provide cushioning.

This shoe incorporates fast-draining features as well as anti-microbial material to keep the shoe dry and hygienic, even when you might not be!

Buy from Musto

Best Men's Boat Shoe-Olukai

OluKai Moku Pae

Specifications | Sizes: 7 through 15 | Colors: Multiple shades of blue, white, and gray | Construction: Lined mesh

Reasons to Buy:

– Great aesthetic.
– Collapsible heel for slip-on ease.
– Non-marking and good traction.

Reasons to Avoid:

– Might not be as stable as high-performance trainers.

Olukai is a brand more often associated with Hawaii-inspired sandals than sailing shoes. But their Moku Pae model brings the same Aloha vibe to a serious boating tread.

Like all of the best men’s boat shoes, it is as comfortable and stylish off the water as on a boat. A full mesh upper and stretch tongue with no-tie laces add to the contemporary aesthetic.

The collapsible heel make the Moku Pae both a shoe and slide, depending on your mood. But this footwear is not built only for style points.

An EVA midsole enhances comfort, and Olukai’s wet-grip rubber sole and tread pattern provide sure footing on deck.

The Moku Pae is available in a range of colors and sizes, and it tends to accommodate wide feet better than many traditional boat shoes.

Buy from OluKai

Buy from Amazon

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