The 5 Best Sailing Shoes for 2021

Boat shoes have been a huge hit since they were first developed in 1935 by Paul Sperry.  These shoes are ideal for boating and sailing adventures, but they have actually become so popular that people all over the world have started wearing them as everyday shoes.  

The best sailing shoes can be worn by men and women alike and are both stylish and casual! 

The Best Sailing Shoes to Get Now

Some of the best characteristics of traditional boat shoes are that they’re super comfortable to wear, offer excellent traction thanks to their non-slip sole, and can protect you from most environmental conditions. Let’s face it, these shoes already look pretty fantastic because of their authentic leather construction and functionality. In this review, we’re going to compare some of the best boating shoes to include in your shoe collection this year!

1. Sperry Men’s Authentic Original 2-Eye Boat Shoe - The Overall Best Boating Shoes

These shoes by Sperry aren't just our top pick because they're made by the creators of boating shoes, but due to their diversity. These shoes are perfect for men, women, and children because they come in a variety of sizes and colors. With their wide selection of colors, you’re bound to find a pair that matches your style perfectly!

Most Sperry's have a 100% leather upper construction, but some pairs are made with a combination of leather and textile fabric. Their pure leather shoes offer great durability and are water-resistant once you treat the leather with the right products. 

On the other hand, their textile fabric pairs are a bit lighter and more breathable, which might make them more suitable for hot weather. The extra padding around the ankle also offers good cushioning to keep you nice and comfortable throughout the day.  

These shoes have non-slip rubber soles that are ideal for walking on slick surfaces. The rubber soles do have a few traction nodes, but some buyers actually prefer a bit more traction on the sole. Inside the shoes, there is an EVA heel cup that offers even more cushioning.  

Overall, it’s a great shoe and brand to consider if you’re looking to stock up on a wide range of stylish boating shoes!


  • Weight: 11 Ounces
  • Size: 4.5 - 16, including wide size options
  • Color: Variety
  • Upper Material: Leather
  • Sole Material: Synthetic
  • Footbed: EVA heel cup


  • Beautiful design 
  • Available in a huge variety of solid colors and color
  •  combinations
  • Variety of sizes, including wide size options
  • Uppers are made from 100% genuine leather
  • 360 degree lacing system is very functional
  • Comfortable fit
  • EVA heel cup offers a firm fit 


  • Non-marking rubber sole needs more traction nodes
  • Possible squeaking sounds when wearing
  • Not 100% waterproof

Timberlands are also great shoes for sailing, amongst other activities. These 2-eye boat shoes offer a classic look in five beautiful colors. You can also get them in a wide range of sizes which makes them practical for both men and women.  

These boating shoes are made with 100% leather uppers. These leather uppers offer good durability and can be turned into waterproof material simply by applying the right leather treatments to your shoes. Leather treatments will also help to keep the shoes nice, soft, and increase their durability.

The shoes have a solid rubber sole with a small 0.5-inch heel. This heel is ideal for people who want a little bit more support on the backs of their feet. The rubber traction sole does offer quite a bit of slip resistance, but some buyers feel that a little bit more traction would have made them feel safer when on slippery surfaces.  


  • Weight: 1.1 Pounds
  • Size: 6.5 - 14, including wide size options
  • Color: Rootbeer, Dark brown, Navy, Navy smooth, Tan
  • Upper Material: 100% Leather
  • Sole Material: Rubber sole
  • Heel Height: 0.5 Inches
  • Footbed: Leather lining


  • Made from 100% leather
  • Available in five different colors
  • Available in a variety of sizes, including half sizes for wider feet
  • Insoles are removable
  • Heel is nice and low for a firm footing
  • 360 degree lacing system helps create a more custom fit


  • Sizes run small
  • Comes with half an inline 
  • Need more traction nodes on the soles

The Margaritaville Men's Anchor Lace Boat Shoe are an ideal investment for the summer because they have a mesh construction to help keep your feet nice and cool on hot days. The mesh fabric also allows your feet to dry off quicker in case they get wet.

These shoes are only available in three different colors, but they’re still a stylish choice! They are available in a wide range of sizes.The uppers are constructed from genuine leather and mesh to offer great durability. These shoes also offer lots of padding around the ankle to keep you nice and comfortable throughout the day.

The rubber soles are designed for superior traction. They have a flashy anchor design on the base of the shoe with lots of traction nodes to keep your feet nice and firm on a wet deck. These really are the perfect style investment!  


  • Weight: 2 Pounds
  • Size: 7.5 - 14, including wide size options
  • Color: Brown, Light tan, Gray
  • Upper Material: Mesh and Leather
  • Sole Material: Rubber with anchor print
  • Footbed: Foam insole


  • Beautiful design
  • Mesh upper fabric sides will keep your feet nice and cool
  • Nice anchor print on the rubber soles
  • Rubber soles are thick for extra comfort
  • Made with genuine leather uppers
  • Collar is soft and padded for additional comfort
  • Extra traction makes them ideal for wet surfaces
  • Quick to dry
  • Available in many sizes, including wider sizes


  • Not 100% waterproof
  • Only available in three colors
  •  Non-leather laces

These Dockers are a good budget option if you need a durable pair of boating shoes that look smart and offer good functionality. These shoes are available in three different colors and in a handful of different sizes.  

The uppers of these shoes are hand-sewn from 100% genuine leather. With the right leather care treatment, these shoes can become water-resistant and last longer.

We love the extra traction on the rubber soles of these shoes. The traction nodes offer good grip on slippery surfaces and the slight heel offers good foot support. These shoes are also fitted with a genuine leather cushioned liner and an EVA heel cup to keep your feet nice and comfortable if you’re standing for long periods of time.  


  • Weight: 13.2 Ounces
  • Size: 7 - 15, including wide size options
  • Color: Rust, Raisin, Tan
  • Upper Material: 100% Leather
  • Sole Material: Rubber
  • Footbed: Cushioned EVA footbed with molded EVA heel cup


  • Stylish classic design
  • Made from 100% leather
  • Rubber soles are ideal for walking on either wet or dry surfaces
  • Traction nodes will keep you from falling on a slippery surface
  • EVA footbed is cushioned with a molded EVA heel cup
  • Available in a variety of sizes, including wider sizes
  • Available in three different colors
  • Great for any type of sailing


  • Sizes run small
  • Not 100% waterproof
  • Insoles may become loose after frequent wearing

These boating shoes by Rugged are another great budget option. You can get these fine quality shoes in five different colors and in a variety of sizes, including wide size options. 

These boat shoes are made with 100% leather uppers and extra padding around the foot for enhanced comfort. The rubber, non-marking soles are very similar to the original boating shoe design, but they can be a bit slippery and squeaky. These shoes are fitted with the traditional 360 degree lacing system so you can create a more custom fit.  


  • Size: 8 - 13, including wide size options
  • Color: Blue, Brown, Gray, Tan, Two-Tone
  • Upper Material: 100% Leather
  • Sole Material: Rubber


  • Classic boat shoe design
  • Available in five different colors
  • Slip resistant bottom is functional for wet conditions
  • Upper is made from 100% premium grade leather
  • Odor control tech allow you to wear the shoes without socks
  • Resistant leather will keep your feet warm
  • Leather is a tad thicker than the average leather boat shoes


  • Lack of sizes
  • Need more traction on the soles 

Buying Guide

Are you having a tough time choosing the best sailing shoes? Well, we don’t blame you, because all of our picks are very stylish and ideal for sailing. To help make it a little bit easier, read our handy little guide below!

The Best Authentic Pair

If you’re buying boating shoes with authenticity in mind then it’s best to go back to where these shoes began! Sperry’s are our top pick because they offer the widest selection of colors, sizes, and are the original boating shoe style!

Timberland’s are also a good pick if you want an authentic shoe. They feature a very traditional design and are made from high-quality materials.  

The Best for Slippery Decks

For extremely slippery decks, we recommend the Margaritaville shoes. These shoes are designed with a grippy rubber sole to keep you nice and steady, no matter how high those waves might get!

The Dockers are a good alternative because they also have lots of traction nodes and are stylish for any occasion.

The Best Budget Shoes

If you’re shopping on a tight budget then you need to consider Dockers or Rugged Shark. Both of these shoes are made from quality materials at a very affordable price.  

Final Thoughts

We’re confident that any of these sailing shoes will get you through another exciting sailing adventure without the risk of slipping or falling. We hope that this review and guide helped you find the right pair! If you’re in the market for other shoes, like the best road bike shoes, then feel free to take a look at some of our other guides. We also offer useful advice on the best ways to take care of your shoes. With our site, you can find a good pair of shoes for any occasion, sport, or activity!


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