The 15 Best Waterproof Boots For Men

Sep 23, 2020

Category: Style

Spring and summer are full of amazing outdoor memories — many of which can be attributed to the shoes on your feet. Whether you’re making the trek to your favorite neighborhood eatery, or you’re headed into the wilderness for a weekend getaway, one of the most underappreciated items in your wardrobe might just be your boots, sneakers, or sandals. But when inclement weather decides to show its ugly face, what’s the first thing that comes to your attention? That’s right, it’s your soaked-through socks.

For those of us who have been victimized by a sudden downpour, slight drizzle, or obnoxious spill, it’s a lesson that we’ve learned the hard way. Luckily, there’s a way to ensure that you’ll never have to worry about soaked-through shoes again: the waterproof boot. In today’s market, there are more manufacturers to choose from than ever. Once you’ve got a style, trait, or type in mind, it’s easy to find the water-resistant offering that’ll fit your preferences. This is doubly true for the heritage boot genre, which is the most likely to offer waterproof, weather-ready examples to wearers. Below, we introduce a handful of favorites that have helped to turn even the bleakest rainy days around and send them packing.

Native Fitzsimmons Treklite Ripstop

We’re starting our weather-weary list with the Native Fitzsimmons. It’s difficult to find a boot that’s more capable than this one at the sub $70 price point, but thanks to the brand’s affordable manufacturing practices, you’ll be able to partake in pleasantries like ripstop nylon, Scotchgard Defender water repellency, and PU backing, without having to spend a ridiculous amount of money to get there. Since the Fitzsimmons is both reliable and stylish, it’s the perfect boot for those who are looking to strike a balance between a wearable urban stomper, and a trail-savvy wilderness silhouette. Tack on some soft microfleece lining, a two-part outsole, and a compression-molded EVA midsole, and you’ve got one of the most affordable, weatherized footwear essentials on the market today.

Purchase: $65

Sperry Top-Sider Men’s Avenue Duck

As the last of our sub $100 offerings, the Sperry Top-Sider Men’s Avenue Duck is an attractive, reliable offering that pulls heavy inspiration from L.L.Bean’s timeless rainy-day model. Each example is fully seam-sealed and features a stain and water-resistant leather that promotes comfortable wear during long commutes. Pair that with a fully-lined shaft, a memory-foam footbed, and thermal lining, and this quintessential Duck boot checks all the boxes for those who are looking to confront everything from a moderate drizzle to a full-fledged downpour.

Purchase: $65

Tretorn Gill

Tretorn has a knack for the creation of contemporary footwear, and the Gill is no exception. Not only does this boot deviate from the traditional silhouette and shape of a waterproof rain shoe to provide wearers with more urban appeal, but it’s also equally as stunning when used as a traditional, everyday shoe. Its mid-top design is accented by the brand’s unique lace-up rubber/coated canvas construction, an EcoOrtholite high-performance internal sock, and an ultra-grippy outsole catered toward use in both wet and dry environments. If you’re looking for a pair of boots that you can swap out for your traditional mid/high-tops on a rainy day, we think that the Gill is the ultimate compromise.

Purchase: $120

Timberland 6” Waterproof

Timberland is a juggernaut within the boot industry, especially when it comes to heritage-inspired examples. The 6” Waterproof, for instance, adopts the brand’s flagship design and gives it a bit more gumption for those days where moisture control is key. These stylish offerings feature an outdoor silhouette that’s seam-sealed, padded, and durable, standing up to even the most stubborn liquids for guaranteed waterproofing. Of course, it also holds true to the brand’s timeless style, incorporating a substantial premium leather upper, classic boot laces fashioned from 100% recycled nylon, and rustproof hardware that’ll help you to weather the storm for years after purchase.

Purchase: $140

Hunter Refined Slim-Fit Chelsea

It’s often difficult to find modernized renditions of tried and true classics. That’s especially true when it comes to the Chelsea boot – – a stylish, fashionable example that’s regularly included in many formal wardrobes. An utterance of the name doesn’t inspire feelings of wet-weather credibility, especially when faced with inclement downpours; but, thanks to Hunter’s Refined Slim-Fit Chelsea, that’s all about to change. This urban silhouette features a new, tailored shape that’s been handcrafted from natural rubber and vulcanized for unprecedented protection from the rain. All the trappings of a traditional Chelsea boot are still here, however. Elasticated gussets/goring, a nylon pull tab, and a stylish, black silhouette round out the Refined Slim-Fit for wearers who want to retain their stylish sensibilities during those gloomy days.

Purchase: $155

Dr. Martens 1460

Like L.L.Bean and Timberland, Dr. Martens is a mainstay within the boot space. While their offerings are far more urban, the expertise that they’ve garnered over the years isn’t squandered. Instead, boots like the waterproof 1460 provide capable respite from the masses of stylish leather examples within their catalog, bridging the gap between fashion and functionality. The introduction of the waterproof 1460 model came almost 60 years after the icon’s first manufacturing run, but that doesn’t stop it from capturing all of the unique intricacies of the original. A twin heat-sealed welt joins with the boot’s air-cushioned sole, breathable DryWair bootie, and oiled leather material to stand up against harsh spills, puddles, and rain. But what about the aesthetic pleasantries of Dr. Martens’ legendary boots? Don’t worry; the shoe’s DMS tread pattern, yellow stitching, and two-tone sidewall are still instantly recognizable.

Purchase: $160

Blundstone Stout Chelsea

Blundstone’s Stout Chelsea is yet another formidable, weatherized offering that takes on the style icon’s unique silhouette. While it’s not as modern as Hunter’s Slim-Fit, it still boasts a lean profile, square toe, and a dressy appearance, overall. The Stout is obviously chained to the historic lineage of the original, but that isn’t a knock against its water-deterrent capabilities. It features a premium brown leather construction, brown, elasticated goring, and a TPU outsole for positive traction on a variety of surfaces, wet or dry. To augment its classic presence, an SPS Max Comfort system has been included (to provide increased shock absorption), while the boot’s cushioned midsole promises a more comfortable fit.

Purchase: $195

Danner Mountain 600 Insulated

Danner is a prominent inclusion that finds its way into almost every boot-focused list that we write, but that’s not because we’re biased. If you’ve been around footwear for any amount of time, it’s likely that you’ve heard of the brand’s lauded models. Their heritage-inspired silhouettes are second to none, and that’s no different for the Mountain 600 Insulated — a performance heritage hiker that’s been treated with the brand’s “Danner Dry” technology. To amplify the boot’s outdoor presence, Danner teamed up with prominent outsole provider, Vibram, to create the quintessential piece of trail-savvy footwear, incorporating a tried-and-true SPE midsole, and Nisqually traction for more dependable trekking. A full-grain leather upper pairs with the 600’s Primaloft insulation, superior cushioning, and lightweight materials to round out the wet/dry wonder, which acts as an introductory model to Danner’s Performance footwear lineup.

Purchase: $220

Arc’teryx Acrux TR GTX

Arc’teryx is most notable for its outerwear, but that doesn’t mean that it can’t create a pair of great outdoor boots. The Acrux TR GTX is a testament to that fact, thanks to its technical orientation, SuperFabric upper, and increased support, making it a great option for hikers/trekkers who travel long distances. To give the Acrux its own unique traits, Arc’teryx has incorporated an interesting micro-plated system, allowing the boot to remain inherently flexible, abrasion-resistant, and light. This, paired with a proven GORE-TEX insert, helps to provide ample mobility in even the most dastardly conditions.

Purchase: $240

Red Wing Classic Moc

Like Danner, Red Wing is an iconic name within the boot space. Hailing from Minnesota, the brand has crafted more durable footwear offerings than we can count, and out of them, the Classic Moc is certainly one of its most regarded. While the boot has taken on different roles over the years, it’s stayed true to Red Wing’s original design, incorporating heritage-inspired traits, up-and-coming materials, and an exceptional outdoor design that’s allowed the brand to adapt and overcome throughout the generations. The most recent iteration of the boot arrives as a capable moc toe, adopting Puritan triple stitching and a reinforced storm welt for unprecedented water resistance. If you’re looking for an iconic piece of footwear that’ll take on the flooded trail with ease, but can still adapt to the urban environment, the Red Wing Classic Moc is for you.

Purchase: $290

Filson Uplander

Filson’s Uplander boot was built to take on the PNW’s forested regions, so you can bet that it’s got some form of waterproofing. To battle the rugged, wet environment, each boot adopts a heavyweight, full-grain leather, a foot-conforming cork insole, and a grippy Vibram outsole for traction on moist surfaces. Like others on this list, it features fully-sealed seams, staving off water from its exterior before it penetrates to the layers below. As a result, your feet are guaranteed to stay dry, warm, and comfortable. Once the boots start to fall apart, you’ll be able to re-sole them, thanks to the Uplander’s included Goodyear welt. If that’s not an attractive long-term investment, we don’t know what is.

Purchase: $375

Trickers Burford Plain Derby

Trickers’ Burford Plain Derby is a marked return to our waterproof style offerings. This contemporary classic features a clean, unassuming design, paying homage to the Derbys of generations past. However, this unique model also features a bellows tongue, which can be folded and attached to provide a watertight seal between the elements and the tops of your feet. To ensure that you’re protected on all fronts, the Burford also incorporates an additional storm welt, providing ample resistance between the shoe’s sole and upper. Stylish, minimalist footwear has never been so prepared to take on a slight drizzle.

Purchase: $570

Grenson Vincent

Grenson’s Vincent is a great-looking Veldt style that pays homage to the original Veldtschoen boot, which was used by Afrikaner soldiers during the Boer War. The return to form calls upon a technical upper that eliminates the gap between the boot’s sole and upper material, resulting in a watertight seal. Pair that with Grenson’s premium black Reindeer leather, a grippy, and durable commando sole, and a distinctive hatch-grain that gives the boot is own unique aesthetic, and you can see why Grenson is one of today’s most prominent footwear providers.

Purchase: $660

Viberg Country

Viberg’s boots are always among our favorites on every list that we write. The Country, for example, is a handsome recreation of the traditional British hunting boot, giving it an edge on its competition in terms of cleanliness and reputable style. While it’s been built to take on the brush, it’s also well-versed in terms of water-resistant protection, thanks to its 360-degree vamp and interlocking eye stay. A premium leather exterior pairs with the boot’s stitch down construction, classic round-toe, and grippy Ridgeway outsole.

Purchase: $700

Church’s Worthing

Church’s rounds out our list with the Worthing — a fashionable, formal boot that features a unique buckle fastening at its opening. A more utilitarian play on the traditional Chelsea, this iconic piece brings a durable, and dependable 103 last, rounded toe-box, and thick double-sole to the forefront for stylish wearers. It also incorporates a gunmetal buckle, polished binder, and an incorporated storm welt for increased rain protection. This, paired with Church’s revered internal lining, handwritten accents, and crest, provide boot lovers with a subtle style piece that can be worn during some of the city’s most depressing drizzles.

Purchase: $790

The 12 Best Waterproof Sneakers For Men

If you’re looking for something a bit more casual and/or athletically-oriented, you can still gain access to superb weatherproofing. Find the perfect pair of shoes for that pursuit on our list of the best waterproof sneakers.

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