Winter and fall are wonderful for a whole mess of reasons. However, footwear isn’t one of them. No matter how much designers may try to class it up, it’s inevitable that waterproof boots are going to be heavy, clunky, and cumbersome. They sort of have to be, if they’re going to keep the elements out.
Take it from someone who has weathered some of the harshest climatic conditions the United States can dish out: when it comes to winter footwear, the key is to embrace function over form. Pack away your best suede oxfords, your canvas slip-ons, and even your bespoke leather boots until May, and find yourself a tough pair of shit-kickers built from natural rubber, Gore-Tex, and pure grit. They may not be stylish, but boy, will they make you feel like a badass. Which, if you didn’t know, is also the best way to keep warm.
Related Guides:
Our lineup of the best waterproof boots will not only keep your feet toasty and dry but make you feel impervious to the most punishing elements. Go ahead, weather — do your worst.
Best All-Purpose Waterproof Boot
We had a tie for this one.
First, a classic: the Vasque Sundowner. The timeless simplicity and time-tested ruggedness of the Sundowner are the result of full-grain leather from a Minnesota tannery, Gore-Tex waterproofing, and the legendary Vasque Pyrenees outsole. With all this and an enduringly handsome profile, too, we’d have stopped right here, if it wasn’t for the fact that Vasque has incurred the displeasure of longtime loyalists as a result of a drop in the boots’ legendary quality (the result, some saw, of having relocated their boot manufacturing site from Italy to China).
With that in mind, meet the Forsake Range, a “sneakerboot” that does a damned convincing impression of a duck boot. They combine the stability of a hiking boot with the comfort and flexibility of a running shoe. The waterproof but breathable membrane within its seam-sealed leather upper offers all-weather protection and durability, while the composite shank, extra wide footprint, and Vibram Megagrip outsole offer great traction in treacherous precipitation.
Best Waterproof Boot for Rain
What makes LaCrosse such a legendary brand? Maybe it’s the uncompromising, hand-laid natural rubber construction. Maybe it’s how the boots perform in mud like a monster truck. Maybe it’s the Chevron Cleated Outsole, fully vulcanized onto the boot to ensure it never separates. All that really matters is that you have a pair of these Grange boots ready when the skies open. If they’re good enough for Grandpa, they’re more than good enough for you.
Best for Waterproof Boot Outdoor Activity
From end-of-season chores to a snowy hike on a bluebird day, the waterproof Danner Arctic 600 will keep a spring in your step. The renowned Danner silhouette is enhanced with an ultra-cushy Vibram SPE midsole. Ice and snow are no match for the traction supplied by a Vibram Nisqually Arctic Grip outsole, nor the warmth of 200G PrimaLoft insulation.
Best Waterproof Boot for Snow
This is where the rubber meets the road. Or in this particular case, the three-foot drift. If you’re rocking a pair of Baffin Icebreakers, you’ve got nothing to worry about. The only thing more mind-blowing than the squishy waffle footbed cozy internal lining (good all the way down to -94 degrees Fahrenheit) is their feather-light weight. I’ve been wearing Baffins for five years and still get compliments on them from hardened Yoopers (translation: “residents of Michigan’s Upper Peninsula”) who barely crack a smile at the best of times.
Best for Maximum Style
If the most weather your feet see is the sprint from subway stop or parking lot to the shelter of home or office, you still need a good pair of waterproof boots for winter, just a pair with a little more panache. For those who favor classic heritage styling, we recommend Red Wing’s new Sawmill Six-Inch boot. This boot is tight as a drum, with water resistance guaranteed by a storm welt and moisture-wicking lining, but softened with nubuck leather, a deerskin collar, and a felted wool footbed.
For those whose sartorial sense has a Euro-modernist lean, the Charlie boots by Norwegian brand Swims offer iconic Scandinavian style in vulcanized rubber with an anti-slip grip.
Editors' Recommendations
- When You’ve Got a Job to Do, You Need a Pair of the Best Work Boots for Men
- Yes, You Can Still Wear Shorts This Fall and Stay Warm. Here’s How
- Men’s Fall Fashion Trends and Essentials: 2020 Style Guide
- The Best Hiking Boots for Men, From Lightweight To Ultra-Plush
- 90’s Fashion Guide: How to Get The 1990’s Style
