The Complete Guide To Red Wing Boots

Photo: Red Wing Roughneck

Few footwear companies can match the time-tested prestige of Red Wing — a Minnesota-based outfit that built its fabled boot collection around, and for, America’s hard-working tradesman. When it comes to established renown, the brand’s various models have weathered the centurial storm thanks to unparalleled durability, comfort, and performance, making them a staple for any avid worker.

But that doesn’t mean that Red Wing trades solely in workwear. In fact, the company’s Heritage line is a great example of stylish staples that have been revived, reintroduced, and repurposed for a more fashionable audience. In this guide, we take a look into the current offerings from the brand’s Heritage lineup and dive into what makes them such a prominent style pick for the modern man.

6-Inch Boots

The Stylish Utilitarians

Weekender Chelsea

Red Wing’s Weekender Chelsea is a more relaxed version of the brand’s formal boots, but that doesn’t make it any less notable. Its unique stitch-down silhouette was conceptualized and implemented specifically for the Weekender line and boasts a full-grain olive-brown roughneck leather exterior, Comfort Force Footbed, and Hill sole to provide wearers with unparalleled comfort when compared to the brand’s other variants. Better yet, a tailored interior fit has been introduced to keep the boot secure and streamlined, while leaving space for your toes to move and breathe — something that’s often lost on other, more narrow Chelsea styles.

Purchase: $240

Classic Supersole

The Classic SuperSole is right in-line with Red Wing’s heritage outlook, and as one of the most legendary boots in its catalog, this resurrected silhouette has become a calling card for stylish, leather-wearing guys everywhere. The SuperSole was originally released all the way back in 1981, and since then, it’s remained relatively tame when it comes to looks and construction. Where most might spout the old adage, “if it isn’t broke, don’t fix it,” the SuperSole has been tastefully revised for the contemporary market, boasting newly-implemented gunmetal hooks and eyelets for enhanced visual appeal. A Chevron SuperSole and Goodyear Welt keep the boot firmly rooted in its past, while the implementation of Copper Rough & Tough Leather provides a glorious patina over years of wear.

Purchase: $270


The Rover focuses on Red Wing’s history as one of the world’s premier work boot proprietors. Forged in the fields and the factory, these rough and rugged six-inch offerings merge the genres of lifestyle and work, creating a great-looking variant that doesn’t fall short of the brand’s hard-working pedigree. On its interior, a Cushion Crepe shock-absorbing sole complement’s the shoe’s full-grain Amber Harness Leather upper, insole, and cork midsole, which has been lauded as one of the boot’s most personable features, adapting and molding to the shape of your foot over time.

Purchase: $270


The Men’s Wacouta boasts an outdoor appeal that just can’t be beaten, and thanks to its moccasin-inspired silhouette, comfortability is king when it comes to this boot. Not only is it light, dependable, and flexible, but it also calls upon a variety of mixed materials, including waxed canvas, premium Briar Oil Slick Leather, and stitch-down construction to keep everything held together. To round things out, a Vibram Honeywheat Mini-lug outsole and No. 63 last have been implemented, providing unparalleled traction, grip, and foot security.

Purchase: $270

Classic Moc

In some circles, the Classic Moc is perhaps Red Wing’s most illustrious shoe. It was introduced all the way back in 1952, and today, it boasts much of the same styling, stitching, and fashionable presence as it did all those years ago. After being marketed as a sportsman’s boot, the long-lasting icon became renowned for its Moc-toe construction, Traction Tred rubber outsole, and Puritan triple stitching, making it one of the most legendary variants around. This, paired with the implementation of well-wearing Black Prairie Leather, keeps the Classic Moc as relevant today as it was during its debut.

Purchase: $280


The Roughneck is a rugged boot that’s built on Red Wing’s most iconic last, No. 23. Introduced in the 1950s, it was a mainstay in the company’s preliminary offerings and sought to change the footwear world forever with a durable, long-lasting platform built for technical use. A Goodyear Welt, Vibram Lug sole, and full-grain Briar Oil Slick Leather adorn the Roughneck’s exterior, giving it an aggressive, but refined attribution. Although the silhouette was originally built for rig workers, these durable leather boots have become increasingly sought after for use alongside stylish ensembles, the world over.

Purchase: $280


The Blacksmith six-inch boot prides itself on its versatility. It was originally introduced to bridge the gap between the workshop and more formal occasions, acting as an adaptable variant that could take on the intricacies of the factory and field, and transition semi-effortlessly into the world of late-night banter. At first, the Blacksmith boot was designed to protect workers’ feet and ankles from hot cinders as they shot off the forge, but eventually, the shoe’s full-grain Black Prairie Leather would be seen as something much more stylish. Now, a grippy Vibram 430 Mini-lug sole and three-quarter Goodyear welt provide exceedingly-dependable traction for all-season use.

Purchase: $300


In the early years of Red Wing, salesmen and merchants needed to find a dependable way to bridge the gap between their more professional attire, and their street-ready outfits. Traversing the cobblestone roadways caused lesser footwear to wear out and fizzle, but Red Wing’s Merchant boot — a timeless staple from the era of stylish implementation — was something different. This versatile boot boasts a Puritan triple stitch construction, an Amber Harness Leather upper, and a Chemigum rubber outsole to provide adequate traction, without feeling too cumbersome.

Purchase: $320

Iron Ranger

As one of the oldest shoes in Red Wing’s repertoire, the Iron Ranger is a look into the earliest days of the brand. These vintage boots were introduced in the 1930s for miners who spent their days pulling valuable metals from the earth, and have since transcended the boundary of workwear to become something much more pronounced. A long-lasting toe cap, speed hooks, and Vibram 430 Mini-lug outsole have been implemented alongside a dependable Goodyear Welt, full-grain Copper Rough & Tough Leather upper, and nickel eyelets to illustrate how an almost-hundred-year style can remain relevant today, especially when it comes to heritage menswear.

Purchase: $330


The Sawmill boot was a turning point for Red Wing as a brand, acting as a segway for the company’s first textile breakthroughs and weatherization techniques to take hold. This cold-weather silhouette was built to provide unparalleled water resistance, warmth, and comfort for those facing abnormally-chilly winters, and called upon a moisture-wicking lining, felt wool footbed, and storm welt to bridge the gap between dry indoor conditions, and wet, raining days. This, paired with the boot’s Puritan Triple Stitch construction, Vibram TC-4 Plus outsole, and premium Oil Slick Leather, make the Sawmill a timeless hit among fans. Plus, an included deerskin collar can’t hurt your style points, right?

Purchase: $340

Williston 6-Inch

Red Wing’s Williston series is, perhaps, it’s most refined, tracing its lineage all the way back to dress models built in the ’20s and ’30s. Honoring one of the company’s earliest investors, the Williston 6-Inch boot is one of two premium offerings that are widely considered to be the brand’s most illustrious, calling upon traditional craftsmanship, ultra-high-quality Teak Featherstone Leather, and a dependable Gro-Cord outsole to ensure unparalleled lustrousness throughout its life.

Purchase: $430

Williston Chelsea

Like its counterpart, the Williston 6-Inch, the Williston Chelsea boot honors one of the brand’s earliest investors, making it a top-tier offering among an already-illustrious catalog. This slip-on style didn’t make its way into the company’s arsenal until the 1990s, but that doesn’t make it any less notable. Calling upon Red Wing’s premium Black Featherstone Leather, 220 last, Gro-Cord outsole, and Goodyear Welt, this upper-echelon example believes simplicity is key, opting to exclude any unneeded hardware or branding to keep things formal and fashionable.

Purchase: $450

8-Inch Boots

The Most Well-Known

8-Inch Classic Moc

At the moment, Red Wing’s 8-Inch Classic Moc is its only offering in the Heritage eight-inch realm, making it a sole survivor whose role is immediately apparent. As the brand’s only eight-inch variant, the Classic Moc is likely Red Wing’s most well-known, harkening back to the golden era of the 1950s, where it was introduced as the quintessential huntsman’s boot. Due to the company’s lineage, the 8-Inch Classic Moc would eventually transition to the job site, followed closely by use for conventional, everyday wear. On its exterior, an iconic Traction Tred rubber outsole, Puritan triple stitch construction, and Goodyear welt provide unparalleled dependability for relentless wear, while a water-resistant, full-grain Oro Legacy Leather, nickel eyelets, and No. 23 last round things out.

Purchase: $300

Chukka Boots

The Informal Middlemen

Weekender Chukka

The Weekender Chukka serves as an entry-level offering for the brand’s laid-back half-lace line. This stylish-but-relaxed replica of the Weekender Chelsea 6-Inch is essentially the same as its counterpart, utilizing a flexible stitch-down construction, Hill outsole, and Olive Brown Roughneck Leather to provide a great-looking segway into the brand’s more illustrious offerings. But, since it’s a Chukka, it might come off as a little less formal than its laceless companion, so be wary.

Purchase: $230

Postman Chukka

The Postman Chukka takes an iconic Oxford silhouette and adds a hint of informal prestige. Relying on Red Wing’s Black Cushion Crepe Wedge outsole, Corrected Grain Black Chaparral Leather, and black eyelets, this stylish take on the classic postman’s shoe provides wearers with a unique mixture of leather and lace, calling upon old-school styling, a resoleable 210 last, and a sweat-proof leather insole to provide intrinsic comfort throughout the day, regardless of the miles you put in.

Purchase: $260

Work Chukka

Finally, Red Wing’s Work Chukka rounds out our list as the final Heritage offering in the company’s expansive catalog. As the most subjectively-stylish example in the company’s Chukka line, this Copper Rough & Tough Leather-imbued shoe provides a more refined take on the half-lace style, calling upon an ultra-durable Atlas Tred outsole, Goodyear Welt, and nickel eyelets to work in tandem with Red Wing’s other silhouettes. The result? A versatile shoe that transitions well from the workplace to the bar, and boasts inherent qualities that are well-suited to bending and kneeling throughout the day.

Purchase: $260

How To Take Care Of Leather Boots In Winter

If there’s a season that goes hand-in-hand with boot-wearing, it’s gotta be winter. But your cold-weather footwear, as tough as it is, still requires a bit of love and maintenance. Learn everything you need to know on our guide to winter leather boot care.