Best Sperry Shoes For Sailing

Whether you’re a casual sailor or a well-weathered skipper, Sperry has everything you need when it comes to the best shoes for sailing. As you look for shoes to take on your next onboard adventure, there are a few factors to keep in mind, like non-slip soles, water resistance, and comfort. Check out the list below for some of our favorite pairs with these features.

But first, let’s talk about a key detail that makes Sperry the ultimate choice for seafaring footwear: razor-cut Wave Siping™ technology.

Razor-Cut Wave-Siping™ Technology
We can’t talk about the best sailing shoes without mentioning our patented razor-cut Wave-Siping™ technology. When Paul Sperry slipped off his boat, the Sirocco, in the early 1930s, he found inspiration in the natural texture of his dog Prince’s footpads that never seemed to slip, even on ice. By cutting patterned grooves into blank rubber shoe soles, Paul Sperry developed the world’s first non-slip boat shoe (now known as the Cloud CVO Deck Sneaker) that later evolved into a signature Sperry design detail that’s still used in our shoes today.

Sperry has a long history of supporting the sport of sailing for more than 80 years, and the SeaHiker™ Dinghy Boot is Sperry’s latest in pure performance sailing boots for beginner to professional sailors. The SeaHiker™ Dinghy Boot was made specifically for competitive sailors, making them the best sailing shoes.

We worked with elite sailors to create the best sailing shoes for racing by innovating the right balance of protection, comfort, and durability to be at peak performance on the open water. The SeaHiker™ Dingy boot is made from flexible rubber and is outfitted with a non-marking rubber outsole with Adaptive Wave Siping™ technology for enhanced wet/dry traction. Paired with adjustable ankle straps and a side-lace entry for a customizable fit, all you have to worry about is making it to the finish line.

The one that started it all. Sperry’s first-ever shoe, the CVO Deck Sneaker, first hit the waves in 1935 after our founder, Paul Sperry, slipped and fell off his sailboat. Each pair of CVO Deck Sneakers is outfitted with razor-cut Wave Siping™ technology or wavy lines cut into the soles of each sneaker, designed to trap water and give you better onboard traction. Signature Sperry style combined with ultimate wet/dry traction makes the CVO Deck Sneaker the best deck shoe for sailing, hands down.

Authentic Original™ Boat Shoe
You can’t beat a classic! We had to mention our Authentic Original™ boat shoe, also known as the best boat shoe for sailing.

Men’s 7 Seas 3-Eye Sneaker / Women’s 7 Seas 3-Eye Sneaker


Don’t just take on the high seas — take on the whole world with the 7-Seas 3-Eye Sport Sneaker. Featuring a drainage port design and quick-drying materials this sport sneaker is one of the best deck shoes for sailing. This flexible, breathable shoe moves with you as you man the helm, but the razor-cut Wave-Siping™ technology keeps your step steady as you beat upwind. The non-marking rubber outsole ensures your boat stays scuff-free, and the 360° Lacing System™ technology creates a snug, customized fit.

Women’s SeaCycled™ Headsail Sneaker / Men’s SeaCycled™ Headsail Sneaker


Our Headsail Sneaker is perfect for all-day adventures at sea. Made with quick-drying materials, they’re water-friendly and have drainage ports for convenience and breathability. Plus, a molded EVA footbed provides extra cushioning and shock absorption for those crashing waves. These sport sneakers feature our Adaptive Wave Siping™ technology to enhance your traction from wet to dry surfaces, so you can keep your footing and turn the helm with confidence. Because as Paul Sperry once said, “A wet deck is a damn dangerous thing.”

Men’s SeaSock™ Water Shoe / Women’s SeaSock™ Water Shoe


Calling all summer recreational sailors—this one’s for you! A water shoe with a sock-like feel, our form-fitting, performance SeaSock™ water shoe is made with quick-drying mesh materials for convenience and ventilation. With both front and back pull-tabs, they’re easy to slip on/off and feature our Adaptive Wave Siping™ technology for enhanced traction on slippery surfaces. Another great shoe for dinghy sailing, the SeaSock™ water shoe maintains a great grip on deck and also protects your feet from ocean floor debris, so even if you run aground, you don’t have to worry about stepping on sharp shells while you push your boat back to deeper waters.


From surf to scramble, from sail to trail, the Eagle Ray Sport Sandal is a tough, lightweight strap sandal designed to perform through the rigors and demands of a day on the sea, stream, and shoreline. Made for land and sea, the Eagle Ray makes an excellent sailing shoe for its quick-drying neoprene/synthetic upper, secure heel straps, and adaptive Wave-Siping™ technology for non-slip traction on deck. Plus, the molded EVA footbed provides cushioning and shock absorption for all-day wearable comfort.

Women’s Water Strider / Men’s Water Strider


The Water Strider is the perfect family-friendly, all-purpose water shoe, featuring a versatile slip-on construction that’s designed to stay securely on the foot throughout all of your on-deck activities. Its tailored size and shape hug the foot, and while this shoe isn’t exactly a waterproof sailing shoe because of its drainage holes around the surface, its quick-drying hydrophobic materials won’t absorb water. A non-marking rubber outsole with adaptive Wave-Siping™ technology disperses water underfoot to enhance traction on wet or dry surfaces, making these shoes another excellent sailing shoe option.

Men’s Cutwater Deck Boot / Women’s Cutwater Deck Boot


Take command of the deck with the Cutwater Deck Boot. One of the best sailing shoes for its rugged, versatile nature and easy on/off rubber upper, the Cutwater is engineered to deliver performance on deck and rinses quickly for the next adventure. The perforated neoprene collar dries quickly, and the vulcanized construction provides a durable finish so you can wear these shoes for many adventures to come. Of course, the Cutwater features our signature Sperry razor-cut Wave-Siping™ technology, and as an added bonus, this shoe comes in tons of different colors to match your on-deck fit.

Men’s Wave Rocker


The Wave Rocker is a performance piece of footwear designed with as much speed and power as your boat. This sailing shoe is also one of the best powerboating shoes because of its unique design. Featuring a soft, perforated neoprene sock fit upper supported by an innovative external harness, this deck shoe provides a top-of-the-line custom fit and lateral support. Pound the waves, ride the seas, kick them off and they’ll be ready for your next adventure.