Mens Cushioned Boots

Step into comfort and durability with our collection of mens cushioned boots. Designed to keep your feet supported and comfortable on any adventure, these boots offer lasting value and timeless style. Whether you're trekking through rugged trails or navigating city streets, the versatile designs ensure you’re ready for whatever the day brings. With a focus on quality and easy-to-use features, our mens cushioned boots are perfect for those who love exploring the great outdoors without compromising on comfort.

Sort by:

Filter & Sort

298 Items

Men's Storm Chaser Boots 5, Zip

A rugged all-weather boot in oakwood with waterproof leather, PrimaLoft® insulation, and easy side zip.

Pros: Comfortable for long hours Easy on/off with zipper closure Durable and well-made Warmth in cold weather Good traction and grippy sole
Men's Stonington Boots, Moc-Toe

A rugged dark oakwood leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.

Pros: Durable construction Versatile use Lightweight design Stylish appearance Comfortable fit
Men's Storm Chaser Boots 5, Leather Lace-Up

A durable, waterproof leather boot with PrimaLoft insulation and EVA midsole for all-weather comfort and support.

Pros: Perfect fit Great quality High comfort Improved traction Excellent warmth
Men's Bean Boots, 8" Shearling-Lined Insulated

A Maine-made boot with buttery-soft leather, plush shearling lining, and waterproof rubber bottom for cold conditions.

Pros: High durability Made in the USA Stylish appearance Excellent warmth Comfortable fit
Men's Bucksport Boots, Cap Toe

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 Weather Challenger Insulated Boots
Price was from: $199 now: $149

A pair of insulated leather/rubber boots with 600g PrimaLoft® insulation, ideal for sub-zero conditions.

Pros: Perfect fit Exceptional warmth Reliable waterproofing Great flexibility Excellent traction
Men's Apex Wading Boots, Studded

A pair of gray studded wading boots with durable Aramid fibers and Vibram Idrogrip rubber soles.
Men's Stonington Chelsea Boots, Leather

A rugged dark oakwood leather pull-on boot with sneaker-like comfort and durable VertiGrip rubber outsole.
Men's Keen Targhee IV Mid Waterproof Hiking Boots

A waterproof leather hiking boot offering stability, support, and comfort with eco-friendly features and durable traction.
Men's Cresta II Waterproof Hiking Boots, Leather

A brown leather hiking boot with waterproof membrane and Vibram® sole for rugged, all-weather traction.
Men's Stonington Boots, Suede Moc-Toe
Price was from: $170 now: $144

A rugged, deepest brown suede moc-toe boot with sneaker-like comfort and all-day support.
Men's Bean Boots, Canvas Rubber Mocs
Price was from: $99 now: $74.99

A Maine-made, waterproof canvas moc with durable triple-needle stitching and a long-lasting rubber outsole.
Men's Allagash Handsewn Chukka Boots
Price was from: $180 now: $149

An ash-colored suede leather chukka boot with handsewn construction, ergonomic footbed, and lightweight lugged outsole.
Men's Bean Boots, Gumshoes

A Maine-made, weather-ready gumshoe with durable leather/rubber construction, triple-needle stitching, and enhanced comfort.
Men's Stonington Chelsea Boots, Suede
Price was from: $150 now: $124

A rugged, deepest brown suede boot with sneaker-like comfort, shock-absorbing insole, and durable rubber outsole.
Men's Mountain Classic Quilted Ankle Boots II

A pair of quilted ankle boots with a rubber outsole, offering supreme comfort and thermoregulating lining.
Men's Bean Boots, Slip-On Rubber Mocs

A weather-ready slip-on moc with waterproof rubber bottom, tumbled leather upper, and cushioned dual-density insole.
Men's Down East Utility Boots, Insulated
Price was from: $159 now: $119

A pair of dark mushroom leather utility boots with PrimaLoft insulation and VertiGrip outsole for all-day comfort.
Men's Dirigo Hiking Boots, Waterproof
Price was from: $149 now: $99.99

A lightweight, ultra-cushioned hiking boot with a waterproof membrane and superior traction, available in deep brown.
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 comfort and durability.
Adults' Blundstone 500 Chelsea Boots

A pair of premium black leather pull-on boots with shock-absorbing construction and cushioned comfort for all-day wear.
Men's Bean Boots, Rubber Mocs

A weather-ready brown leather and rubber moc with enhanced comfort, waterproof protection, and durable slip-on design.
Men's Lacrosse Alpha Deck Boot, 6"

A waterproof, rugged 6" deck boot with slip-resistant outsole, premium rubber, and 3.5mm neoprene core.
Men's Storm Chaser 5 Chelsea Boots

A rugged, waterproof Chelsea boot with PrimaLoft insulation, moisture-wicking mesh, and a siped rubber outsole.

Mens Cushioned Boots

When it comes to choosing men’s cushioned boots, a few thoughtful considerations can make all the difference in comfort, performance, and lasting value. As the first cool winds of September roll in and outdoor adventures beckon, cushioned boots become a reliable companion for everything from morning commutes to weekend hikes. The hallmark of a great cushioned boot is its ability to keep feet comfortable and supported, even after hours on the move. Look for boots with premium insoles that offer ample cushioning—features like memory foam or contoured footbeds can help absorb shock and reduce fatigue, whether you’re navigating city sidewalks or forest trails. Durable outsoles, especially those made from flexible rubber or wedge designs, not only add an extra layer of comfort but also provide dependable traction on a variety of surfaces. High-quality materials like full-grain leather or rugged synthetics ensure boots are built to go the distance, season after season, while thoughtful design touches—such as padded collars and gusseted tongues—help keep debris out and comfort in.

Men’s cushioned boots are a versatile choice for a wide range of lifestyles. They’re a staple for anyone who spends long hours on their feet, from teachers and tradespeople to outdoor enthusiasts and everyday explorers. The extra support and shock absorption are especially appreciated during autumn’s busy days, when errands, work, and recreation often blend together. Slip-on Chelsea styles with elastic side panels offer easy on-and-off convenience for those quick dashes out the door, while lace-up designs provide a more secure fit for extended treks or unpredictable terrain. These boots also make a thoughtful, practical gift for dads, sons, friends, or partners—anyone who values comfort and durability in their daily footwear. And for those looking to take their adventures to new heights, there’s a natural progression to more specialized options, like our Men's Climbing Boots, designed for even greater support and rugged performance.

No matter where your path leads this fall—through leaf-strewn parks, bustling city streets, or winding country roads—men’s cushioned boots are designed to keep you comfortable and confident every step of the way. Their timeless style pairs seamlessly with jeans, work pants, or outdoor gear, making them a reliable choice for both everyday wear and spontaneous outings. Easy to care for and built to last, these boots embody the spirit of getting outside and making the most of every season. With the right pair, you’ll be ready for whatever the day brings, from crisp morning walks to evenings by the campfire, all while enjoying the enduring comfort and support that only a truly well-crafted boot can provide.

It's time to upgrade your browser

Mens Cushioned Boots