Sperry Cutwater Review

9.7 score
[Editors rating (9.7)] = (WalkJogRun) score (9.7)/10

Editor rating: 9.7 / 10
User's rating: based on 0 user ratings
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Whether you’re sailing or hiking, the Sperry Cutwater is the perfect pair of boots to keep you dry and comfortable! This deck boot offers lightweight insulation and a water-resistant build that ensures all-day comfort while you’re out and about. With the feel of an old pair of sneakers and the protection of a boot, this is the ideal choice for all of your outdoor adventures. A well-tractioned outsole offers superior grip and a secure lace system helps to keep the Cutwater securely on your feet so you can forget about your boots sliding off.

Sperry promises the same level of quality that they're notorious for and more with these boots. They've pulled all the stops and made this one of the most comforting and enjoyable choices of water-resistant footwear on the market. Fleecy lining and a light Thinsulate padding ensure that your feet stay warm and toasty, even during winter weather. This is one of the reasons that people turn to the Cutwater for winter wear because it's waterproof and keeps you nice and warm

These boots come in three fun and stylish colorways that will have you looking sharp while you're on the go. Their nautical-inspired vibe and smooth silhouette help to make this boot a must-have for anyone who wants to stay dry while trudging through wet and rainy conditions. They come highly rated with wearers from all over the globe and deliver a solid plethora of benefits just to good to ignore.

Editor's Pros & Cons
  • Rubber Duck Shell
  • Wave-Sipping
  • Lace-Up 
  • Full-Grain Leather
  • Removable EVA Footbed
  • Wide Fitting
  • Minimal Arch Support


This boot has got it all going on! Its full-grain leather upper unit is designed to keep you comfortable even after hours of wear. The leather material is breathable and helps to prevent overheating that can lead you to start sweating. Excessive sweat breads the perfect environment for the growth of odor-causing bacteria, but the leather material wicks excess moisture away from the skin. This combined with the Cutwater’s protective rubber duck shell ensures that your feet will stay nice and dry no matter how wet and rainy the weather is.


The Cutwater offers a removable footbed for superior comfort. It’s made from molded EVA, a man-made foam resin material that’s super lightweight. The foam provides superior cushion and helps to better absorb the waves of shock from every step. This prevents arch pain by shielding the delicate underside of the foot and protecting the sensitive arch area. A removable footbed is a good choice because you’re able to wash it separately from the rest of the boot. You can also remove it completely and use your own custom orthotic inserts with ease.


Sperry is notorious for its unique tread pattern, known as Wave-Siping. This innovative design better disperses water which allows for superior wet and dry traction. The Cutwater will keep you steady on your feet no matter the conditions and guarantees secure footing whether you’re at sea or hiking off-trail, this pair has got you covered from top to bottom. The sole is made from 100% rubber which is the most water-resistant material and guarantees you’ll stay as dry as can be. Its rubber duck design covers more area of your feet which helps to prevent water from seeping inside through the upper unit.

The Cutwater was designed with a rugged yet sneaker-like outsole that offers the ultimate in comfort and versatility. Go ahead and sail the seven seas or trek through the wilderness with ease thanks to this pairs adaptable design and sturdy sole that is ready to take on whatever may come your way.


If you’re shopping for a boot to keep you warm and toasty then this is the best choice for you! The Cutwater offers an upper unit that’s fully lined with soft fleece for added warmth. It also has Thinsulate in the upper, shell, and footbed for even warmer wear. These boots are perfect for chilly days thanks to their superior lining materials that combine to form a protective barrier between you and the cold. It's important to keep your feet warm when the weather is cold because otherwise, you'll be more vulnerable to colds, flu, and even frostbite when it's super cold.


If you’re a sailor at heart then you’ll love the three different colorways available. The Cutwater comes in three striking options which include Black/Noce, Olive/Off-White, and Tan/Navy. These selections are nautically-inspired and offer the perfect look for wet and rainy days. Most people find that these boots are easy to match with practically any style of clothing thanks to their neutral tones that look good with almost any other colors.


This boot is available in half-sizes which is very convenient and helps them to fit much better. They come in a medium width so those who have wider feet shouldn’t feel too cramped in them. Overall, most wearers find that these boots are very comfortable to wear and that they fit true to size. Those who have narrow feet might consider opting for a half-size smaller than normal, though they aren’t overly wide so you should be okay with your normal size.


The Cutwater was designed with a protective rubber shell that covers more of the foot than the average rubber sole. This heavy-duty shell surrounds the upper foot too and ensures that no water leaks inside through the upper. Rubber is one of the best materials for wet weather because it’s completely waterproof. It’s also durable and long-lasting so you won’t have to worry about replacing your shoes as often.


These Sperry boots offer innovative Wave-Siping technology. This uniquely designed tread pattern is made through the use of small slits along the rubber sole. Those, combined with bigger wave-like grooves work to completely repel water away from the sole. It also provides superior grip so you won’t have to worry about any accidental slips or falls.


Despite this pair being listed as medium width, many people find that they’re just too wide. In fact, some people even have to buy a half-size smaller than they normally would in order for them to fit properly. They run fairly true to size in terms of length, but the width is way more than it should be. It’s important that your shoes not be too wide because they will be uncomfortable to walk in and can even cause you to trip if they’re too wide.


Despite their overall comfort, these boots don't offer much in the way of support. The arch is fairly low to the ground and isn't enough to properly support some wearers. If this is an issue for you, try adding your own insert, which is easy-to-do thanks to the Cutwater's removable EVA insole. This lets you easily insert your own custom orthotic or simply a store-bought insole that provides a more supportive structure. Just be aware that these boots may not be solid enough on their own and be prepared to purchase a separate insole if that's something you might feel you need.

Bottom Line

Overall, Sperry Cutwater is an excellent pair of boots! They’re made for wear in wet and even snowy weather and promise to keep your feet perfectly dry no matter the conditions. This boot is a great choice for anyone who enjoys sailing the seas or hiking through nature thanks to its rubber sole and innovative Wave-Siping traction that offers superior grip on practically any kind of surface.

Sperry has been a trusted name in sailing shoes since 1935 when Paul A. Sperry first introduced the world to boating shoes. Sperry’s Top-Sider footwear has become infamous in the sailing communities and is considered by many to be the only shoe worthy of sailing in.

The Cutwater lives up to this brand's notorious name and delivers a comforting ride that guarantees you’ll stay nice and dry no matter the weather. It offers a ton of beneficial features like fleece lining for added warmth and a protective rubber shell that encompasses more of the foot.

These boots run true to size but are much wider than the medium-width that they’re labeled as. People with narrow feet find that ordering a half-size smaller than normal helps to offset their super-wide structure and makes them more comfortable to wear.