Best Sailing Shoes Reviewed & Rated for Quality

In a Hurry? Editors choice:
Sperry Men's Original 2-Eye
Test Winner: Sperry Men's Original 2-Eye
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Picture this. You’ve done it. You’ve actualized a lifelong dream. You’ve finally gotten your own sailboat. She’s a beauty like no other.

You take her out for the first time--out on the open seas. Every inch of her is shining and the light reflecting off the water is etherial. You inhale deeply to take it all in, and then your gaze falls to your feet.

You’re wearing sandals...with socks.

This is simply not good enough for your gorgeous boat. If she could, she would spit you out. After all, sailing is not just a pastime, it’s a lifestyle. Keyword being “style.”

But don’t you worry. We have sailed the internet seas to bring you the best sailing shoes on the market today. These shoes boast incredible craftsmanship, extreme comfort and functionality, and classic style that will complete your dreams and make you the perfect match for your sailing beauty.

Standout Picks

Sperry Men's Original 2-Eye Sailing Shoes
We kickstart our list with one of the most iconic and recognizable sailing shoes of all time--the Sperry Men’s Original 2-Eye. As far as men’s sailing shoes go, these are the pinnacle. These are some of the best shoes for sailing out there and it’s clear to see why they’re such a seminal favorite. Their classic style and comfortable fit make for a great match while you’re navigating the open seas. And while we are featuring the Sperry Men’s here, Sperry makes excellent Women’s sailing shoes as well.
Amazon Link
$51.24
Timberland Men's Classic 2-Eye Sailing Shoes
We’re coming at you with another Classic 2-Eye, this time made by Timberland. While your mind may jump to construction lace-up boots, let us assure you that Timberland makes some fine shoes for sailing as well. These are a deep dark brown that will offer hours of comfort and a pop of style to any sailing outfit.
Amazon Link
$124.96
Tommy Hilfiger Men's Bowman Sailing Shoes
The Tommy Hilfiger Men's Bowman is another looker to make our list. With tons of different style and color options to choose from, the only problem you’ll have is just selecting one. Perhaps your compass will help you choose!
Amazon Link
Sperry Men's Sea Kite Sport Moc Sailing Shoes
The Sperry Men's Sea Kite Sport Moc is the second Sperry product to make our list, but hey, can you blame us? These shoes have a totally different construction and look to make them an ideal companion for super wet conditions while offering up a ton of breathability as well.
Life Outdoors Men’s Slip On Sailing Shoes
The Life Outdoors Men’s Leather Slip On is another that takes a slightly different look than your standard classic 2-eye boating shoe. While these maintain the same classic leather construction, the shape is unique and serves to offer up tons of support and security.
Amazon Link
$79.99
CLARKS Men's Waterloo
The CLARKS Men's Waterloo is another great option if you’re looking for more form and stability in your shoe. These have a larger footprint (no pun intended) and are desgined to be more supportive and comfortable for longer wears.
Amazon Link
Sperry Men's Salt Washed
Ok. We promise this is the last pair of Sperrys to make our list. The Sperry Men's Salt Washed is not a leather shoe, like so many others on our list. Rather, this product is made from 100% canvas and performs like a dream in wet conditions. Plus, they look incredibly hip while doing so.
Amazon Link
Dr. Comfort Men's Diabetic
The Dr. Comfort Men's Diabetic is a shoe that was developed using tons of research. This shoe is designed specifically for those suffering from diabetic foot diseases, though these shoes can be enjoyed by all--especially for those who are looking for supreme comfort in a shoe.
Amazon Link
Base London Joplin Slip On
The Base London Joplin Slip On is one of our favorite looking shoes. Made from suede on the inside and out, this puppy was designed to keep you styling and profiling. Plus, it offers up tons of flexibility and lightweight comfort for whatever your offshore day throws at you.
Amazon Link
Columbia Men's Perfect Cast Sailing Shoes
The Columbia Men's Perfect Cast is the perfect way to round out our list. This is a classic shoe with a straightforward design that is meant for the water, and is the perfect companion for casting out the perfect line on your favorite fishing rod. With specially treated leather, you’ll be able to enjoy this shoe for a long time.
Amazon Link

Criteria Used for Evaluation

Materials

When considering the products that would grace this Ten Best List we first looked at the materials that each product is made out of. All of the products on our list are made from 100% genuine leather. While some feature synthetic netting and mesh for breathability, every single leather detail is all leather.

Comfort

Because these products are meant to be worn for long periods of time out on the water, we wanted to ensure that we were bringing you comfortable products that you could actually wear all day long.

We go into how to wear in your shoes below in the Frequently Asked Questions section, so we won’t say more on that here, but many of the products on this list provide additional comforts and padding so that you can focus on sailing and not on achy feet.

Durability

As these shoes are a bit pricy by nature, we wanted to make sure that they can stand up to the test of time. That’s why we delivered a list full of genuine leather shoes.

We go into detail below in the Expert Tips section on how to best care for your new kicks in order to extend their lifetime.

We also remind you that the leather is more durable than the sole, so it’s worth investing in an inexpensive resole than ordering a new pair altogether.

Style

Sailing is more than just a sport--it’s a lifestyle. And fashion is at its core. That’s why we searched high and low to bring you the most functional and best selling products on the market today.

Value

As always, we are super invested in the value of each of our products. These shoes have a super long lifespan and provide the comfort, support, traction, and style that you require for long days out at sea.

10 Best Sailing Shoes

1. Sperry Men's Original 2-Eye

Where to buy
Amazon Link
$51.24
Sperry Men's Original 2-Eye Sailing Shoes
Amazon Link

We kickstart our list with one of the most iconic and recognizable sailing shoes of all time--the Sperry Men’s Original 2-Eye. As far as men’s sailing shoes go, these are the pinnacle.
These are some of the best shoes for sailing out there and it’s clear to see why they’re such a seminal favorite. Their classic style and comfortable fit make for a great match while you’re navigating the open seas. And while we are featuring the Sperry Men’s here, Sperry makes excellent Women’s sailing shoes as well.

Hand Sewn
The Sperry Men's Original 2-Eye is gorgeously constructed. These shoes are comprised of 100% genuine and premium leather with Tru-Moc construction. They are hand-sewn for unmatched quality. You can purchase these in a variety of rich colors. Some of our favorites include Sahara, Black, Classic Brown, Amaretto, and White.

Even the laces on the Original 2-Eye are made from 100% rawhide. And the lacing system extends 360 degrees around the ankle (behind the heel, and tying in front). Plus, the lacing eyelets are rustproof so you won’t have to worry about them weathering when the shoes are exposed to moisture and water.

Soles Won’t Mark
The Sperry Men's Original 2-Eye boasts a few essential design features that are critical for long days at sea.

With a heel cup made from EVA foam, the base of the shoe works to absorb shock and provide long-lasting comfort.

Plus, the rubber sole of the shoe is non-marking which means no scuff marks all over your pristine sailing beauty. And the soles feature a wave-siping razor cut traction pad that will maintain grip even on slick wet surfaces.

Cost and Value
The Sperry Men's Original 2-Eye rings up at the bottom of our price range and we love its value because it is a tried and true classic that combines gorgeous craftsmanship, leather, and functionality all into a long-lasting shoe that can handle long nautical hours offshore.

Amazon Link
$51.24

2. Timberland Men's Classic 2-Eye

Where to buy
Amazon Link
$124.96
Timberland Men's Classic 2-Eye Sailing Shoes
Amazon Link

We’re coming at you with another Classic 2-Eye, this time made by Timberland. While your mind may jump to construction lace-up boots, let us assure you that Timberland makes some fine shoes for sailing as well. These are a deep dark brown that will offer hours of comfort and a pop of style to any sailing outfit.

Nubuck Uppers
The Timberland Men's Classic 2-Eye features all leather uppers made from premium quality Nubuck leather. This is a full-grain leather that offers up tons of breathability and long-lasting wear.

The uppers are fully hand-sewn so you can be sure you are going to be getting a high-quality shoe that lasts. They are attached to the midsole with stitching which is practically cemented onto the outsole so you can count on these shoes for years to come.

These shoes are not only attractive, but they are also super comfortable. They feature EVA padding in the insole of the foot so you can wear these for hours without experiencing any foot aches and pains.

Rawhide Laces
The Timberland Men's Classic 2-Eye features a full round lacing system that allows you to get a personalized fit, no matter your shoe size. The lacing system extends around the heel and ties at the front. This product features rawhide laces that can hold up to the test of time.

With rubber durable outsoles that are fully siped for supreme traction, you can handle a few errant waves without worrying about your footing on board.

Cost and Value
The Timberland Men's Classic 2-Eye rings up at the bottom of our price range and we love its value because it is a beautifully handcrafted product that is both durable and comfortable, so you can really get your money’s worth out of them.

Amazon Link
$124.96

3. Tommy Hilfiger Men's Bowman

Where to buy
Amazon Link
Tommy Hilfiger Men's Bowman Sailing Shoes
Amazon Link

The Tommy Hilfiger Men's Bowman is another looker to make our list. With tons of different style and color options to choose from, the only problem you’ll have is just selecting one. Perhaps your compass will help you choose!

A Wide Range of Style Options
The Tommy Hilfiger Men's Bowman comes in an array of different style and color options. You can pick these up in all of the usual browns, but you’ll also be able to choose from light blues, two-tones, and grays.

Plus, there are shoes that come in the standard leather (pictured), and these are most ideal for actual boating. But there are also suede accent options, as well as pocked leather options for an even jazzier look.

But no matter which style you choose, you’ll enjoy the subtle difference of color between the laces and the leather shoe body as each pops the other one off.

Made from Authentic Leather
The Tommy Hilfiger Men's Bowman is made from 100% genuine leather (and some suede). The laces are made from leather as well.

The lacing system extends fully behind the foot and is enclosed in the ankle padding so that you can achieve a snug and personalized fit so as not to lose a shoe when you are busy boating. This product features real metal eyelets.

Plus, the soles are made from leather that won’t leave scuff marks--even when they’re wet.

Cost and Value
The Tommy Hilfiger Men's Bowman rings up towards the bottom of our price range and we love its value because it comes in so many different style and color options so any boater can find the right style to suit their personal aesthetic.

Amazon Link

4. Sperry Men's Sea Kite Sport Moc

Where to buy
Sperry Men's Sea Kite Sport Moc Sailing Shoes
Amazon Link

The Sperry Men's Sea Kite Sport Moc is the second Sperry product to make our list, but hey, can you blame us? These shoes have a totally different construction and look to make them an ideal companion for super wet conditions while offering up a ton of breathability as well.

Thicker Soles
The Sperry Men's Sea Kite Sport Moc is the perfect shoe if you are looking for something with a little bit more cushion and support in the sole. With about an inch more of cushion, you will be able to feel the difference the first time you put them on--not to mention several hours after. Plus, these come with inserts that provide even more padding for your foot and can be removed if you desire.

The rubber bottoms of the shoe also feature full siping on the outsole for supreme anti-slippage in even the wettest boating conditions.

This product features a full round lacing system with synthetic laces that hold up well to getting wet.

Still All Leather Uppers
The Sperry Men's Sea Kite Sport Moc looks far sportier and contains some mesh pieces, but the leather is still 100% genuine. And this leather is treated specifically to resist water damage and to maintain shape and elasticity for a prolonged lifespan.

With mesh lining each side of the shoe, you get breathability that you would not expect from a standard boating shoe. Plus, this design helps the shoes to dry out far more quickly which helps to keep you comfortable for longer.

Cost and Value
The Sperry Men's Sea Kite Sport Moc rings up in the middle of our price range and we love its value because it’s basically like an athletic shoe, a boat shoe, and a moccasin had a baby and you get to enjoy all of the best qualities of each in one shoe.

5. Life Outdoors Men’s Slip On

Where to buy
Amazon Link
$79.99
Life Outdoors Men’s Slip On Sailing Shoes
Amazon Link

The Life Outdoors Men’s Leather Slip On is another that takes a slightly different look than your standard classic 2-eye boating shoe. While these maintain the same classic leather construction, the shape is unique and serves to offer up tons of support and security.

Velcro Closure
The Life Outdoors Men’s Leather Slip-On features the leather construction that you would expect from a boat shoe, but one that is slightly more flexible for your comfort.

Rather than having a lacing system, this shoe features a velcro closure that will strap you in tight with ease. This feature means that you can slip the shoes on and off in a matter of seconds so you can work on that shoe tan while you’re out on the water.

The footbed of this shoe is covered in leather and mesh which works to keep the sole breathable and helps it to dry more quickly.

The outsole of this product is fully siped which works as a sort of water repellant and helps to keep your feet glued to the boat so you don’t slip around like you’re on skis.

Ankle Comfort and Support
The Life Outdoors Men’s Leather Slip-On features a fully rolled leather backing all the way around the ankle. This feature serves to provide tons of ankle support and also offers up some nice cushiony comfort that won’t dig into your ankles as you pivot around the boat.

Cost and Value
The Life Outdoors Men’s Leather Slip-On rings up in the middle of our price range and we love its value because they have a classic look with more attention paid to comfort and security so you can rely on them for long hours out at sea.

Amazon Link
$79.99

6. CLARKS Men's Waterloo

Where to buy
Amazon Link
CLARKS Men's Waterloo
Amazon Link

The CLARKS Men's Waterloo is another great option if you’re looking for more form and stability in your shoe. These have a larger footprint (no pun intended) and are desgined to be more supportive and comfortable for longer wears.

Ortholite Base
The CLARKS Men's Waterloo was crafted with comfort in mind. The heel measures almost an inch thick--and that’s an inch of comfort delivered right to you. The outsole is made of EVA material that is designed to absorb and disperse shock so that you can give your joints a break. But that doesn’t mean it weighs you down. It is still designed to be lightweight.

This product also features a removable Ortholite insert that offers up even more padding to the sole of your foot. Plus, the stretchy give around the upper of the shoe allows you to slip the shoe on and off with ease.

Smooth Synthetic Lining
The upper of this product is made from full-grain leather that is tempered to stand the test of time. And with strategically placed mesh portions, this shoe will dry more rapidly and will keep your foot at a more comfortable temperature as you are wearing it.

The CLARKS Men's Waterloo features a fully and synthetically lined inner. This provides a super smooth surface for you to slip your foot inside which makes wearing this product without socks a totally blister-free experience.

Cost and Value
The CLARKS Men's Waterloo rings up towards the bottom of our price range and we love its value because it offers up tons of support and long-wearing comfort with researched inserts that will hug your feet.

Amazon Link

7. Sperry Men's Salt Washed

Where to buy
Amazon Link
Sperry Men's Salt Washed
Amazon Link

Ok. We promise this is the last pair of Sperrys to make our list. The Sperry Men's Salt Washed is not a leather shoe, like so many others on our list. Rather, this product is made from 100% canvas and performs like a dream in wet conditions. Plus, they look incredibly hip while doing so.

Padded Collar and Tongue
The Sperry Men's Salt Washed features wildly comfortable wear. The collar and tongue on this shoe are padded to protect the sensitive tops of your feet, as well as your ankles.

This product features a “Wave Comfort Foot System” and a polyurethane insert that you can remove to get the stink off if you know what we mean. With a little over an inch in the sole, you will get just the support that you need for long days out at sea.

Canvas Design
The Sperry Men's Salt Washed is the first shoe on our list to be made of 100% canvas. These shoes look and function more like a sneaker, which can be ideal for long days out on the water.

This product comes in an array of dreamy color options, all that are muted and salt-washed for a perfect worn-in look.

Cost and Value
The Sperry Men's Salt Washed rings up at the very top of our price range and we like its value because it is a boating shoe that is totally reimagined and functions much more like a sneaker than the other products on our list. Plus, they are a dream to look at and are as fashionable as they are functional.

Amazon Link

8. Dr. Comfort Men's Diabetic

Where to buy
Amazon Link
Dr. Comfort Men's Diabetic
Amazon Link

The Dr. Comfort Men's Diabetic is a shoe that was developed using tons of research. This shoe is designed specifically for those suffering from diabetic foot diseases, though these shoes can be enjoyed by all--especially for those who are looking for supreme comfort in a shoe.

Designed for Diabetics
The Dr. Comfort Men's Diabetic is specially designed for those with diabetic foot disease. Diabetic foot disease has a range of symptoms that these shoes help to avoid.

Because circulation can be an issue for folks with diabetes, and because ulcers and other complications can develop in a very short amount of time (even during the span of few hours), it is important that those with these conditions take the necessary precautions and get a shoe made just for them.

This shoe has smooth interiors made from leather to cut down on chafing and irritation. The lining is seamless. The inners of the shoe are totally padded for added comfort.
With your purchase, you will receive Dr. Comfort’s gel insert which can be removed based on the wearer’s needs. And it can even be washed to help with stinky feet.

Comes in Extra Wide Sizes
The Dr. Comfort Men's Diabetic is available for purchase in wide and extra-wide sizes. This also helps to eliminate unnecessary pressure that can lead to painful and dangerous foot conditions.

Despite having a greater profile, this shoe is still lightweight. It features a full lacing closure.

You can get this shoe in three different colors: all black, all brown, and a black and brown combo (pictured).

Cost and Value
The Dr. Comfort Men's Diabetic rings up at the top of our price range and we like its value because it offers those with sensitive foot conditions a classicly beautiful and fully functional shoe that will protect their feet from developing painful sores.

Amazon Link

9. Base London Joplin Slip On

Where to buy
Amazon Link
Base London Joplin Slip On
Amazon Link

The Base London Joplin Slip On is one of our favorite looking shoes. Made from suede on the inside and out, this puppy was designed to keep you styling and profiling. Plus, it offers up tons of flexibility and lightweight comfort for whatever your offshore day throws at you.

All Suede Everything
The Base London Joplin Slip-On is made from 100% suede. This suede is ultra-soft to the touch and will hug your foot like a glove. Not only is the upper made from suede, but the lining of the shoe is made from suede as well so it will feel cozy and soft against your foot as you wear them sockless.

We love the moccasin inspired design of the shoe and the additional tassels that set the whole style of the shoe off.

Flexible Sole
The Base London Joplin Slip On comes with an optional insert that can be removed if you desire. It is cushioned and meant to provide a little extra padding and support, especially in the heel.

The flexible outsole allows for a natural range of foot motion and will move with you on long days out on the water. These shoes are super lightweight and won’t be holding your back.

Cost and Value
The Base London Joplin Slip-On rings up towards the top of our price range and we like its value because it is a gorgeous shoe that looks as good as it feels.

Amazon Link

10. Columbia Men's Perfect Cast

Where to buy
Amazon Link
Columbia Men's Perfect Cast Sailing Shoes
Amazon Link

The Columbia Men's Perfect Cast is the perfect way to round out our list. This is a classic shoe with a straightforward design that is meant for the water, and is the perfect companion for casting out the perfect line on your favorite fishing rod. With specially treated leather, you’ll be able to enjoy this shoe for a long time.

Specially Treated Leather
The Columbia Men's Perfect Cast is made from 100% leather--but it’s no ordinary leather. The leather on these kicks has been treated to resist the weathering that takes place with continued exposure to water. Thus, these shoes can hold up to the elements better making them an actual ideal match for sailing.

You can purchase these in 3 colors options: nutmeg and tobacco, abyss and cool gray, and tobacco and sea salt.

Tons of Traction
The Columbia Men's Perfect Cast not only offers up durable leather, but tons of traction in the outsole as well. These puppies will grip so that you don’t end up on your bottom while you’re out at sea. And we love that the outsoles are non-marking so you won’t have to worry about making tracks all over your boat either.

Cost and Value
The Columbia Men's Perfect Cast ring up towards the top of our price range and we like its value because they are treated to resist the wear and tear of water which makes them worth the extra investment as they will last for many seasons to come.

Amazon Link

Sources

  1. Wikipedia Contributing Writers, Diabetic Shoe, Encyclopedia Article
  2. Tarah Damask, What Happens to Suede Shoes When They Get Wet?, Article
  3. Sven Raphael Schneider, Boat Shoes Explained: History, Style, How to Wear Buy & Care Guide, Article