The Best Sailing Shoes

The best sailing shoes need to meet a number of requirements – all equally important for you to be able to enjoy a good day sailing. Many people are happy to use a decent pair of outdoor shoes for sailing in, but others may be looking for shoes that are ideally suited to the job. This is especially important if you plan on sailing for longer periods of time or in rougher weather.

Before you decide on the best sailing shoes for you, take a look at the different types of sailing shoes available.

a man climbing the mast in the best sailing shoes
The best sailing shoes – this post contains affiliate links

Types Of Sailing Shoes

Most sailors these days opt for the more modern, all-weather sailing shoes but it is still possible to get traditional sailing shoes, which tend to be a little more stylish looking and made of natural materials. You can also opt for sailing boots which are especially practical for offshore sailing or sailing in colder climates.

Traditional Sailing Shoes

a man at the helm wearing a pair of the best shoes for sailing
Different types of sailing shoes

Traditional sailing shoes have been around for almost a century. These are the kind of shoes you’ll automatically imagine gentlemen sailors wearing! They’re more of a style statement and don’t tend to be completely waterproof, as they’re usually made from suede leather and are soft and flexible. If you’re planning on coastal sailing on nice, sunny days then opting for something a little more stylish may be right for you. They are still designed for sailing, with flat soles and a non-slip texture designed for wearing on deck.

Modern Waterproof Sailing Shoes

a women working the winches wearing the best sailing boots
The best sailing shoes should be practical and comfortable

As you’d expect, modern sailing shoes use synthetic materials to create waterproof sailing shoes that are practical for all weathers. They have a definite technology advantage over the better-looking traditional sailing shoes, and most are designed with some great extra features to ensure your time onboard is as comfortable and safe as possible.

Sailing Boots

four pairs of sailing shoes on the beach
Flip flops aren’t always your best option!

These are a great option for foul weather sailing, and a useful item of clothing to have in your wardrobe if you sail frequently or are planning a longer trip. These boots resemble snow or rain boots, and they’re made of a waterproof material such as rubber. The downside of sailing boots is that they tend to be a little harder to get around in – think wellington boots but obviously a lot more practical!

Best Traditional Sailing Shoes

High-quality traditional sailing shoes can last you for years and will never go out of fashion on a yacht. Here are our top picks!

Sperry Billfish Boat Shoe

You’ll find a few Sperry boat shoes on our list and for good reason. Sperry has built a legacy of effortless, heritage products over its 80 years, and they’re still just as popular today.

These boat shoes are a great combination of style with some modern features, so you’re getting a bit of both for your money!

These hand-made Sperry boat shoes are water-resistant leather, combined with nylon air-mesh panels so they not only look great but they’re also durable, long-lasting, and supportive. These shoes breathe making them great in all weather – cooler in warmer climates and easy to dry if they get a little soaking!

These shoes are designed for ultimate comfort, fitting well with a secure fit all the way around your feet, not just across your insteps. They have shock absorbers to help prevent foot, leg, and back pain which is especially good if you know you’ll be on your feet a lot. And obviously, they are skid-proof and non-marking.

The women’s version of these boat shoes have all the same great features with a slightly different, stylish look.

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Buy men’s now from West Marine

Buy women’s now from West Marine

The Best Sailing Shoes – Columbia Boatdrainer

These boat shoes don’t look quite as classic as some of the options on here but they do combine style with practicality and comfort. These are the sort of shoes that will work on and off the boat.

Their nubuck leather and mesh uppers feature the advanced water and stain-resistant treatment, making these perfect for not only sailing but fishing too. They drain off the water quickly to keep your feet dry and the mesh helps to keep you cool too. The Omni-Grip™ outsoles ensure you won’t have a problem when the decks get slippery and they also have comfort support insoles to keep your feet from getting tired after a full day out on the water.

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West Marine Men’s Performance Boat Shoes

These are by far the best budget boat shoes out there. You get quality, comfortable sailing shoes for a fraction of the price of some of the other brands out there. Of course, that does mean they’re a little simpler but if you’re after something for weekends out on the water you can’t really go wrong with a pair of these!

They’re water-resistant with drainage built into the outside for quick drying. They’re comfy enough and slip-resistant too! They also look pretty classy.

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Sperry Originals Boat Shoes

The classic boat shoe. You can’t really go wrong with a pair of these for any occasion.

The original Sperry boat shoes are made from genuine all-leather uppers for years of wear. They ‘wear in’ well, meaning they just get more and more comfortable – great for running around on deck all day. You can wear these shoes barefoot or with socks, whatever takes your fancy. Plus they’re obviously designed with excellent grip in mind and are non-marking to keep those decks clean!

Buy men’s now from West Marine

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Best Modern Sailing Shoes

If you’re looking to put practicality above style then you’re not alone. Many sailors are switching out their traditional boat shoes for a more modern, more practical style. If you’re looking for some of the best boat shoes out there then check out these top picks!

Helly Hanson Trysail Boat Shoes

Helly Hanson is well known for their excellent range in sailing clothes, and their shoes are no different. They have a great reputation for producing quality outdoor products that are well researched and designed with sport in mind.

These modern boat shoes are made from a combination of synthetic and mesh for protection, comfort, and breathability. They’re non-marking and the rubber soles give excellent grip in wet or dry conditions. These shoes are made for long days out on the water. They’re lightweight and comfortable, breathable, and have built-in shock absorption to make sure they’re kind to your knees.

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Columbia Tamiami Boat Shoe

Unlike most fabrics that absorb moisture, the Tamiami boat shoe is designed to repel moisture and dries quickly—avoiding stains and keeping you clean. The stain-resistant materials are absolutely perfect for anyone who loves to fish from their boat!

This boat shoe is a lace-up design meaning it fits well to most foot types and the Omni-GRIP outsole matches specially formulated non-marking compounds and a tread designed for maximum wet deck traction. They also look pretty smart too, which is always a bonus!

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Sperry Men’s 7 Seas 3-Eye Boating Shoe

This is one of Sperry’s more modern-looking designs and they haven’t compromised on their usual quality. Perfect for sailing and life around the water, this sneaker is all about performance. Sperry has used hydrophobic materials to resist water and dry quickly. They have their usual signature razor-cut grip to prevent slipping on wet decks, and of course, they are non-marking. These shoes have all the features of the classic Sperry boat shoes but using modern materials and with a more modern look.

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Buy now from West Marine

Best Sailing Boots for Rough Weather

For foul weather sailing, nothing beats a good quality pair of sailing boots. These will keep you dry, warm, and safe without compromising your movement too much. Our top picks are listed below!

Gill Tall Sailing Boot

Gill is another sailing brand with an excellent reputation, and these sailing boots are a great budget option if you’re after a pair of wet weather sailing shoes that don’t break the bank. These boots are comfortable and practical for use in wet weather. They have reasonable grip and although they aren’t as insulated as some other sailing boots out there, there is plenty of room inside for a pair of thick socks!

Just make sure the high leg on these boots will definitely fit you, as with wellington boots they can be poorly suited to some leg shapes.

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Dubarry Ultima Sailing Boots

Dubarry has an unmatched reputation when it comes to sailing boots and it isn’t hard to see why. These sailing boots are not only top quality but they look the part too. These all-leather sailing boots scream quality (and have a price tag to match!) but if you’re looking for a special present for someone or to treat yourself then you can’t go wrong with these sailing boots.

They have a loop to help pull them on, as well as a stretch panel at the back, and they are also available in ‘ExtraFit’ sizes for the wide calved. They grip well, especially after a few uses, and the Gore-Tex lining gives good insulation.

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Huk Sailing Boots

The Rogue Wave sailing boot is shorter than some of the other options on here, making it a little more comfortable for some. Obviously, it’s not quite as waterproof but most of the time you’ll be wearing your sailing boots under foulies anyway, so you probably won’t notice.

Its full neoprene and rubber upper construction provide durability and comfort. It has handy heavy-duty tabs to make getting them on and off easier and a wet traction, non-marking outsole.

Buy now on Amazon

Buy now from West Marine

Hope this article has helped you find the perfect boat shoes or boots for you and your planned sailing goals. We always love to hear about new sailing products, so if you have or have used a pair of sailing shoes that haven’t made our list that you think should then please do let us know by sending us an email at twogetlost at or commenting below! And if you’ve found this post useful then feel free to share it and follow us for more on our social media channels below!

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