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We have curated our top men’s boots, including work, Chelsea, chukka, hiking, and dress styles. These durable boots will last you a lifetime and conquer any weather conditions.
Whether it’s climbing Mount Everest, exploring the streets of Philly, venturing through Jackson Hole, or attending classes at Yale, we rely on our trusty boots to get us where we need to go. Men’s boots have stood the test of time as a staple in any wardrobe because they are durable, fashionable, and reliable.
We have curated a selection of our favorite men’s boots here, including work boots, Chelsea boots, chukka boots, hiking boots, and dress boots. Put on a pair that will last you a lifetime and ensure that no matter the weather conditions – rain, snow, sleet or hail – you can conquer anything that awaits outside.
No matter what kind of adventure you’re preparing for, we have the perfect boot to get you there and back safely. In need of a reliable hiking boot with great traction and a rubber outsole to tackle rocky terrain? Look no further, as we have a wide selection of options for you. Or perhaps you require something tough and durable, like a second layer of skin on your feet. Our curated collection of work boots are just as gritty as you are and unafraid to withstand tough environments to keep your feet fully protected.
RED WING HERITAGE Classic Moc Boot in Alpine Portage
The 6-inch Classic Moc is synonymous with Red Wing Heritage. The boot's unmistakable moc toe and Traction Tred outsole form a silhouette that sets the standard by which all others are measured. Dual-toned stitching and archive-inspired leather elevate the iconic silhouette.
RED WING HERITAGE Iron Ranger Boot in Hawthorne Muleskinner
The Iron Ranger is an American icon beloved for its standout style and long-lasting construction. With its toe cap, speed hooks, and Vibram® outsole, there's no mistaking this leather legend.
The 6-inch Classic Moc from Red Wing Heritage features a distinct moc toe and Traction Tred outsole, creating a timeless silhouette. This particular model (8875) showcases Oro Russet leather and an Irish Setter label inspired by the brand's original best-selling shoe in the postwar era.
The 8-inch Classic Moc stands tall as one of the most iconic boots in the Red Wing Heritage line. Born from the archives, this rugged lifestyle boot is built with the same materials, process and quality as the 1952 original. Oro Legacy leather uses a unique proprietary blend of oils exclusive to Red Wing, allowing the full-grain texture to remain on display without any added pigment.
RED WING HERITAGE Iron Ranger Traction Tred Boot In Oro Legacy
The Iron Ranger Traction Tred is a contemporary hybrid of Red Wing's most iconic styles. Built with the signature Iron Ranger upper and paired with a Traction Tred outsole, this distinctively durable and comfortable boot is the ultimate take on two American classics.
RED WING HERITAGE Classic Chelsea Boot in Amber Harness
The 6-Inch Classic Chelsea in Amber Harness Leather is an American icon beloved for its standout style and long-lasting construction. With its toe cap, speed hooks, and Vibram® outsole, there's no mistaking this leather legend.
The Work Chukka showcases intricate stitching and an Atlas Tred outsole that creates its stand-out look. The boot's casual appearance is easily dressed up for cushioned comfort, and the rugged construction lasts for years.
DECK-BOSS™ footwear is made for anglers who need comfort and performance that lasts through long days on the water. With extra cushioning and an anti-odor liner, these shoes keep you comfortable all day. The razor siping and gum rubber outsole provide superior grip on wet surfaces.
The 12 inch Deck Boot by Grundéns is a durable and comfortable option for anglers spending long days on the water. With a thicker insole for shock resistance and an anti-odor cooling liner, these boots will keep your feet comfortable and fresh. The razor siping and natural gum rubber outsole also provide excellent grip on wet surfaces.
The new Deviation Tall Boot is designed for both on and off deck performance. With over-the-calf protection, it offers versatility and maximum traction on loose and wet terrain. Conquer land and sea with the Deviation Tall.
The Grundéns Freeboard Leather Chukka is designed for comfort, durability, and performance. With a rubber freeboard overlay for waterproofing, full grain leather upper, and siped natural gum rubber outsole, it provides exceptional grip on wet surfaces. Perfect for working on a wet deck or navigating a slippery floor, this style has universal appeal for all anglers.
The Sundowner is an iconic waterproof, leather hiking boot with over 35 years of existence to prove it. Beloved for its timeless style and durability, the Sundowner is in a class of its own.
For over 30 years, the Mountain Light by Danner has been the gold standard in hiking boots for backpackers. And now, the classic design is back, hand-built with full-grain leather and Vibram Kletterlift outsoles in Portland, Oregon. GORE-TEX liners ensure waterproof protection, while a second lace option in flat red adds some style to the comfort and support it provides.
Skyblue Featured Video: First Look: The Modern Version of the Original Red Wing 6-Inch Moc
Red Wing’s reputation is no accident, it’s a result of a century’s worth of premium quality footwear built for hard work. This 6-Inch Moc is designed to break in quickly to get that form-fit, customized feel in a shorter amount of time and continue the legacy of durability that made Red Wing what it is today.
In this first look, Ben from Huckberry unboxes the Red Wing Heritage Alpine Portage Classic Moc and dives deep into the history and construction details that have made the Red Wing Shoe Company so iconic for over a century.
