Men's Waterproof Walking Boots

Step into comfort and durability with our collection of men's waterproof walking boots. Perfect for those who love to explore the great outdoors, these boots are designed to keep your feet dry and comfortable on any adventure. Whether you're trekking through the woods or navigating urban trails, you'll find the perfect pair that blends style with functionality. Experience the lasting value and reliable performance that make these boots an essential part of your outdoor gear. With timeless designs and versatile options, our men's waterproof walking boots are ready to accompany you wherever your path leads.

Sort by:

Filter & Sort

476 Items

Men's Maine Hunting Shoes, 10"

A 10" waterproof leather hunting boot offering superior support and custom fit, made in Maine.

Pros: Favorite boots Lightweight Quiet in the woods Comfortable Vibrant colors
Men's Bean Boots, 10" Shearling-Lined Tumbled Leather

A Maine-made boot in tumbled leather with shearling lining, ideal for cold, wet conditions.

Pros: High quality Waterproof Well-made Comfort Warmth
Men's Bean Boots, 8" Shearling-Lined Insulated

A Maine-made boot with plush shearling lining, waterproof leather, and reliable traction for cold conditions.

Pros: High durability Waterproof quality Made in the USA Excellent warmth Comfortable fit
Men's Bean Boots, 6.5" Chelsea

A legendary waterproof boot with a soft leather upper and durable rubber bottom, perfect for wet conditions.
Men's Bean Boots, 8" Fleece-Lined Insulated

A cozy fleece-lined boot with suede leather upper and waterproof rubber bottom for cold, wet conditions.

Pros: Comfortable design Ideal for snow Perfect size Great color Excellent warmth
Men's Bucksport Boots, Cap Toe
Price was from: $200 now: $169.99

A rugged coffee bean leather boot with Vibram® rubber outsoles and waterproof oiled-leather upper.

Pros: Quality construction Waterproof Great color High comfort Useful side pockets
Men's Trailfinder Hiking Boots
Price was from: $169 now: $119

A pair of waterproof black hiking boots with nubuck leather upper and Vibram® rubber outsole for unbeatable traction.
Men's Bean Boots, Slip-On Rubber Mocs
Price was from: $99.95 now: $84.99

A waterproof slip-on moc with durable leather upper and long-lasting rubber outsole, perfect for wet conditions.
Men's Hybrid Wellie® Boots
Price was from: $119 now: $89.99

A rugged, waterproof boot with nubuck leather, neoprene upper, and VertiGrip rubber outsole for multi-surface traction.
Men's Bean Boots, Rubber Mocs

A Maine-made, waterproof slip-on boot with durable leather upper and long-lasting rubber outsole, perfect for wet conditions.
Men's Bean Boots, Gumshoes

A Maine-made, weather-ready gumshoe with durable leather/rubber construction and a customizable lace-up fit.
Men's Bean Boots, 6"

A weather-ready, Maine-made boot with a supple leather upper and durable rubber outsole for wet conditions.
Men's Bean Boots, 8"

A Maine-made, weather-ready boot with a supple leather upper and durable rubber outsole, perfect for wet conditions.
Men's Bean Boots, 10" Shearling-Lined
Price was from: $299 now: $219

A Maine-made boot with shearling lining, Thinsulate™ insulation, and waterproof leather/rubber for ultimate cold-weather comfort.
Men's Trailfinder Hiking Shoes
Price was from: $149 now: $109

A rugged, waterproof nubuck-leather hiking shoe with Vibram® rubber outsole for unbeatable traction in wet conditions.

Pros: High-quality material Waterproof Good fit Comfortable Nice color
Men's Elevation Hiking Shoes, Waterproof
Price was from: $150 now: $124

A lightweight, waterproof hiking shoe with recycled polyester upper and durable rubber outsole for reliable traction.

Pros: Acceptable color Waterproof protection Comfortable fit

Men's Waterproof Walking Boots

When winter settles in and the trails take on a new personality—muddy, slick, sometimes even snow-dusted—having the right boots can make all the difference. Men’s waterproof walking boots are built for those days when the weather is unpredictable and the ground underfoot is anything but dry. Whether you’re heading out for a brisk morning walk with the dog, exploring local parks with family, or simply want a reliable pair of boots for everyday errands, these boots are designed to keep feet dry, comfortable, and supported through it all. The best pairs combine rugged durability with thoughtful comfort features: cushioned midsoles to soften every step, grippy outsoles for steady footing on leaf-strewn sidewalks or slushy paths, and uppers that fend off moisture without feeling stiff or heavy. With a pair of quality waterproof walking boots, you can step confidently through puddles and over icy patches, knowing your feet will stay dry and comfortable from the first mile to the last.

Choosing men’s waterproof walking boots is about more than just staying dry—it’s about embracing the outdoors, no matter what the forecast says. For many, these boots become a daily staple throughout the colder, wetter months, offering a reliable solution for everything from weekend hikes to shoveling the driveway. They also make a thoughtful gift for anyone who loves spending time outside, whether it’s a dad who enjoys winter walks, a friend who commutes on foot, or a college student navigating campus in all kinds of weather. Because these boots are designed with versatility in mind, they transition seamlessly from trail to town, pairing easily with jeans or outdoor pants and ready for whatever the day brings. The timeless style and lasting value mean they’ll be a trusted companion for seasons to come, making every outing a little more enjoyable and a lot more comfortable.

As you browse options, consider the features that matter most for your needs—like easy-to-use lacing systems for quick on and off, padded collars for ankle support, and interiors that wick away moisture to keep feet fresh even after long hours outside. Look for boots that balance sturdy construction with classic style, so you can count on them for everything from spontaneous weekend adventures to everyday routines. If you’re interested in exploring more choices or need a pair that fits your specific outdoor plans, take a look at our full selection of Mens Outdoor Walking Boots to find the right fit for your next outing. No matter where your path leads this season, the right boots will help you make the most of every step.