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Starting out sailing I didn’t even know you needed special shoes, now that I’ve been in the game for a while I totally understand why! You can get super fancy expensive shoes or you can do what I usually do, find something cheap that is nothing fancy but does the job.
The shoes on this list are not the absolute best out there, but I have tried to find a balance between performance and cost. I hope you find it useful!
Here are the 17 best sailing shoes under $100 in 2022:
- Alibress Men’s Water Shoes
- Sperry Men’s Billfish 3-Eye Boat Shoe
- Columbia Men’s Dorado CVO PFG Boat Shoe
- Dockers Men’s Vargas Leather Handsewn Boat Shoe
- Sperry Women’s Angelfish Varsity Boat Shoe
- Dockers Men’s Beacon Boat Shoe
- MJNY Men’s Casual Genuine Leather Lightweight Boat Shoe
- VILOCY Men’s Slip on Deck Shoes
- BARERUN Barefoot Quick-Dry Water Sports Shoes
- DOUSSPRT Men’s Water Shoes
- DYKHMILY Waterproof Steel Toe Shoes for Men
- Sperry Men’s Authentic Original 2-Eye Boat Shoe
- Crocs Men’s Swiftwater Wave Sandal Flat
- Sperry Women’s Lounge Away Sneaker
- SEEKWAY Water Shoes
- Sperry Men’s Bahama Ii Kick Back Boat Shoe
- Bruno Marc Men’s Slip-On Loafers
Here is my complete Must-have catamaran sailing gear list!
1. Alibress Men’s Water Shoes
These Alibress Men’s Water Shoes (on Amazon.com) consist of waterproof polyester fabric that dries unbelievably quickly, and they have grippy non-slip soles, making them ideal for racing.
In addition to having excellent grip, the soles also have water drainage holes to prevent soggy feet. They also come in a broad range of different colors.
2. Sperry Men’s Billfish 3-Eye Boat Shoe
The Sperry Men’s 3-Eye Boat Shoe (on Amazon.com) is made with 100% genuine leather for a sharp, classy look and soft feel.
Inspired by traditional boating shoe aesthetics, these offshore sailing shoes are as stylish as functional. Their soles also feature advanced shock-absorbing technology for maximum comfort.
3. Columbia Men’s Dorado CVO PFG Boat Shoe
The Columbia Men’s PFG Boat Shoe (on Amazon.com) repels water, stains, and discomfort in style. I chose the tan variation because it’s under $100, but you can also purchase these offshore sailing shoes in black, white, gray, and carbon.
These shoes stand up to the brand name and provide lasting comfort equal to a supportive hiking boot, but they slip off easily, too.
4. Dockers Men’s Vargas Leather Handsewn Boat Shoes
These Dockers Men’s Handsewn Boat Shoes (on Amazon.com) are crafted from 100% genuine leather, and they have long been known as the penultimate classic boating shoes.
This boat shoe, designed with style and comfort in mind, is an excellent option if you’re looking for high-quality traditional sailing footwear.
5. Sperry Women’s Angelfish Varsity Boat Shoe
These Sperry Women’s Varsity Boat Shoes (available on Amazon.com) are genuine leather shoes with a stunning appearance and comfy fit. These classic offshore boating shoes are incredibly durable, aesthetically pleasing, and come in a wide variety of sizes and colors.
6. Dockers Men’s Beacon Boat Shoe
The Dockers Men’s Beacon Boat Shoe (available on Amazon.com) is made from 100% authentic leather.
Traditional sailing styles heavily inspire these shoes, and while a considerable portion of their focus is on aesthetics, they’re equally as functional as they are fashionable. They’re designed with comfort and mind and feature water-resistant technology to keep your feet dry.
7. MJNY Men’s Casual Genuine Leather Lightweight Boat Shoe
The MJNY Men’s Lightweight Boat Shoe (on Amazon.com) is made and stitched by hand in Brazil. It’s carefully made from genuine leather and provides excellent foot support.
They come in brown, black, and tan, and their soles are as soft and comfy as a pillow. These shoes run a bit narrow, so they are the best pick for you if you have slender feet!
8. VILOCY Men’s Slip-on Deck Shoes
These VILOCY Men’s Deck Shoes (available on Amazon.com) are canvas loafers designed for casual wear. They’re crafted from highly durable materials and come with detailed stitching and rigid rubber soles for the most comfort.
They may be slip-on, but they won’t slip off when you’re walking, protecting you from trips and blisters.
9. BARERUN Barefoot Quick-Dry Water Sports Shoes
These BARERUN Quick-Dry Water Sports Shoes (Amazon.com) have a highly functional design featuring flexible fabric, waterproof material, and breathability.
These are great for sailboat racing, but they’re also suitable for leisurely sails.
10. DOUSSPRT Men’s Water Shoes
The DOUSSPRT Men’s Sports Aqua Shoes (on Amazon.com) are ideal for racing, and they are made of waterproof and breathable mesh for maximum comfort.
They’re great for a wide range of aquatic activities and aren’t exclusive to sailing or boating.
11. DYKHMILY Waterproof Steel Toe Shoes for Men
These DYKHMILY Waterproof Steel Toe Shoes (on Amazon.com) are water-resistant and lightweight to ensure the most comfort possible while racing, but they’re also suitable for casual days on land. The steel toe comes in handy if you fish or handle heavy items on your boat since they’ll protect you.
12. Sperry Men’s Authentic Original 2-Eye Boat Shoe
This Sperry Men’s 2-Eye Boat Shoe (on Amazon.com) combines traditional and casual styles, resulting in a shoe perfect for offshore occasions as well as coastal boating. These classic shoes are crafted from a mixture of both genuine leather and high-quality textiles for a sharp look and water-resistant comfort.
13. Crocs Men’s Swiftwater Wave Sandal Flat
The Crocs Men’s Swiftwater Wave Sandal (on Amazon.com) offers a sleek and water-friendly design available in different colors, and they make great racing shoes. In addition to having great waterproof qualities, these Crocs also provide supreme comfort, and they’ll last you a lifetime!
14. Sperry Women’s Lounge Away Sneaker
This Sperry Women’s Lounge Away Sneaker (available on Amazon.com) is a leather-free, breathable, stylish offshore sailing shoe.
I love the gray variation because it’s aesthetically pleasing and perfect for people on a budget, but it does come in different variations. Do keep in mind that the price varies for each color option.
15. SEEKWAY Water Shoes
These SEEKWAY Water Shoes (on Amazon.com) are incredibly lightweight and comfortable. While breathable, they don’t lack substance and have protective rubber soles to keep your feet safe from sharp objects. So, they are fantastic for racing.
These shoes are also ideal for snorkelers and swimmers since you won’t have to take them off when you take a dip.
16. Sperry Men’s Bahama II Kick Back Boat Shoe
This Sperry Men’s Boat Shoe (available on Amazon.com) is a classic choice for sailing. The uppers are made from breathable canvas, and they have tough yet soft rubber soles with a non-slip grip.
I love their plaid design and color palette, which gives you a fun yet classy appearance. They are not waterproof, but they’re comfortable and perfect for offshore wear and casual sailing.
17. Bruno Marc Men’s Slip-On Loafers
These Bruno Marc Men’s Slip-On Loafers (available on Amazon.com) have lightweight mesh uppers and vinyl soles. They’re incredibly light and comfortable, making them optimal for all your casual nautical endeavors.
What Kind of Shoes Are Best for Sailing?
The kind of shoes that are best for sailing are waterproof, comfortable, and have decent grip. Shoes that don’t have these factors will make your nautical endeavors less enjoyable, and they can even be a potential safety hazard. The right shoes will keep you comfortable and keep you from slipping.
However, there are varying factors to consider for every scenario. Different sailing requires various shoes because these scenarios have unique needs, standards, and expectations.
Here are the different categories of sailing shoes:
- Offshore/blue water
- Racing
- Weekend
- Traditional
- Casual (family and friends)
The rest of this section will explain each of these different categories. I’ve also divided the previous list of best sailing shoes under $100 into the categories below so you can better understand which shoes are best for each situation.
Best Offshore Sailing Shoes
Sailing shoes are not exclusive to sailboats. Many people wear them for stylistic preference rather than functionality as a boat shoe. Finding shoes under 100$ that is offshore worthy is hard, here are some that you might look into, but honestly, going offshore I would go for something of higher quality.
Here are the best offshore sailing shoes on our list:
- Columbia Men’s Dorado CVO PFG Boat Shoe
- Sperry Men’s Billfish 3-Eye Boat Shoe
- Sperry Women’s Angelfish Varsity Boat Shoe
- MJNY Men’s Casual Comfortable Genuine Leather Lightweight Boat Shoe
- Sperry Men’s Authentic Original 2-Eye Boat Shoe
- Sperry Women’s Lounge Away Sneaker
- Sperry Men’s Bahama Ii Kick Back Boat Shoe
Sailboat Racing Shoes
Grip, comfort, and waterproof qualities are the most critical factors for sailboat racing shoes. These shoes focus less on aesthetics and more on athletic functionality.
Here are the best sailboat racing shoes on our list:
- Alibress Men’s Water Shoes
- BARERUN Barefoot Quick-Dry Water Sports Shoes
- DOUSSPRT Men’s Water Shoes Quick Drying Sports Aqua Shoes
- DYKHMILY Waterproof Steel Toe Shoes for Men
- Crocs Men’s Swiftwater Wave Sandal Flat
- SEEKWAY Water Shoes
Weekend Sailing Shoes
Different sailing situations may require specific footwear. These shoes are stylish and functional, perfect for a weekend on the water. These selections blend traditional and casual appearance and functionality, making them great for professional and relaxed weekend sailing.
Here are the best weekend sailing shoes on our list:
- Columbia Men’s Dorado CVO PFG Boat Shoe
- Sperry Women’s Angelfish Varsity Boat Shoe
- Sperry Men’s Billfish 3-Eye Boat Shoe
- Sperry Men’s Authentic Original 2-Eye Boat Shoe
- Sperry Women’s Lounge Away Sneaker
- Sperry Men’s Bahama Ii Kick Back Boat Shoe
- Bruno Marc Men’s Slip-On Loafers
Traditional Sailing Shoes
Traditional sailing shoes are typically made from leather and similar materials durable enough for water, wear, and tear. They’re specifically designed to function well on a boat, and they have a formal aesthetic that makes them highly desirable.
Here are the best traditional sailing shoes on our list:
- Sperry Men’s Billfish 3-Eye Boat Shoe
- Sperry Women’s Angelfish Varsity Boat Shoe
- Dockers Men’s Vargas Leather Handsewn Boat Shoe
- MJNY Men’s Casual Comfortable Genuine Leather Lightweight Boat Shoe
- Sperry Men’s Authentic Original 2-Eye Boat Shoe
- Dockers Men’s Beacon Boat Shoe
Casual Sailing Shoes
Casual sailing shoes are perfect for low-pressure sailing with friends and family. You don’t have to worry about keeping your footwear as traditional or formal as possible in these settings.
As long as your shoes are waterproof, comfortable, and have a decent grip, they’re perfect for casual settings.
Here are the best casual sailing shoes on our list:
- Alibress Men’s Water Shoes
- Columbia Men’s Dorado CVO PFG Boat Shoe
- MJNY Men’s Casual Comfortable Genuine Leather Lightweight Boat Shoe
- VILOCY Men’s Slip on Deck Shoes
- DYKHMILY Waterproof Steel Toe Shoes for Men
- Crocs Men’s Swiftwater Wave Sandal Flat
- Sperry Women’s Lounge Away Sneaker
- SEEKWAY Water Shoes
- Sperry Men’s Bahama Ii Kick Back Boat Shoe
- Bruno Marc Men’s Slip-On Loafers
Are Sperry Shoes Good?
You might have heard of Sperry before. They’re one of the most popular nautical footwear brands and have a proud legacy of creating high-quality sailing shoes in a broad range of styles and materials. Still, even with their incredible popularity, you might be wondering whether or not Sperry shoes are all they’re cracked up to be.
Sperry shoes are good options for sailing footwear. This brand is iconic in the sailing shoe industry and has been crafting superior products for decades. If you’re looking for boat shoes that are fashionable as well as functional, Sperry is the way to go.
Sperry has been making boat shoes and accessories since 1935. They have a heavy focus on quality, stylistic tradition, and durability. With over eighty years of experience in their craft, they’re certainly a trustworthy source for all your sailing shoe needs.
Do You Wear Socks With Boat Shoes?
If you’re new to the world of boat shoes, you might be wondering whether or not it’s acceptable to wear socks with sailing footwear.
You can wear socks with boat shoes, but make sure that they are no-show socks that aren’t visible. Socks are vital because they protect your feet from blisters and keep your shoes fresh. However, if you want to look sharp, make sure you keep those socks hidden.
It’s essential (well… sort of) to purchase the right socks for your boat shoes. As I mentioned before, the fashionably-acceptable option is to wear no-show socks. I recommend these IDEGG No Show Socks (available on Amazon.com) for their affordable price, no-slide technology, and breathability.
If you’re wearing waterproof boat shoes, you should consider investing in a pair of water-resistant socks. These Randy Sun 100% Waterproof Socks on Amazon.com are for cycling, but they’re also suitable for water shoes. They’re also no-shows, so you don’t have to worry about breaking any unwritten fashion codes.
Whether or not you’ll be wearing your shoes offshore or on your sailboat, wearing socks with boat shoes is recommended to protect your feet as well as the shoes themselves. However, it’s not completely necessary. The decision is ultimately yours.
