When the rain really starts coming down, you’ll be glad you copped a pair of men’s rain boots…or completely bummed you didn’t. Your sneakers aren’t gonna save you from dreaded wet sock. As the weather gets more volatile every year, checking the forecast is about as good as asking a Magic 8-Ball if it’s going to rain (“without a doubt” sounds sarcastic any way you read it). However the weather shakes out, it’s best to just be prepared, with a raincoat, an umbrella, and certainly a pair of proper waterproof boots.
Rain boots carry an incredible amount of responsibility. Obviously, they should defend your feet from the rain (wet socks are, without a doubt, the most miserable thing we can think of). But rain boots should also keep your feet from slipping and come with a grippy outsole. Think about it: what good is all that waterproofing if you end up falling on your ass? Not only that, they should also work well through mud, slush, and perhaps even snow, answering the high calling of a winter boot. It’s truly a lot to ask of one pair of shoes.
We’re happy to report that there are plenty of choice waterproof shoes on the market that will keep the rain out and look great doing it. So, right now, while you’re all dry and cozy, check out all of the best men’s rain boots to keep you looking fly and drip-dry, from the best sellers to the It Boots of Instagram to the under-the-radar stompers and beyond.
The Best Overall Rain Boot
Xtratuf cut its teeth in the harsh climate of Alaska, earning a reputation for keeping toes bone dry in the face of slushy ship decks and snowy trails. The brand’s Chelsea boots feature an outsole with unmatched traction, a triple-dipped rubber vamp, and full-grain leather ankle that’s completely watertight. Though Xtratuf’s ankle deck boots are perhaps more popular, we favor the Chelsea for its extra flexibility and style.
The Best High-Fashion Flex Rain Boot
The Daniel Lee era at Bottega Veneta might have come to an all-too-sudden close, but the designer’s sculptural, eye-popping boots remain as covetable as ever. And right now, the *most* covetable model in Bottega’s oft-viral stable is the Tire, an exaggerated Chelsea boot with a massive, undulating sole unit that comes in a wide range of stunt-worthy colors—including this iconic Bottega green. It’s the ultimate fashion move in a downpour and, with Lee’s successor Matthieu Blazy now taking the reins, it’s maybe your last chance to own a significant piece of sartorial history.
The Best Beloved East Coast Rain Boot
The archetypal duck boot was born over a century ago and has held its reputation as a go-to waterproof boot ever since. It’s unmistakable rubber toe and outsole give the shoe its signature watertight properties while the gusseted leather portion keeps moisture and debris out. They’re also mad comfortable thanks to the built-in steel shank within the insole, which provides arch support for all-day wear.
The Best Downright Iconic Rain Boot
Hunter is a day-one rubber boot manufacturer dating all the way back to the mid-1800s, when vulcanized rubber first came on the market. In the 1950s, after several decades of supplying waterproof boots to civilians as well as the British army, the iconic Original Boot (aka Wellington, aka Wellies) was born. They’re embraced by everyone from British royalty to everyday gardners and are a wardrobe staple. The Original Boot looks great in its natural habitat with chinos and a waxed jacket, but a track record of high-end collabs with brands like Stella McCartney and Saint Laurent, can easily be worked into your more capital-F fits.
The Best Budget Rain Boot
If you’re not a fan of the cinder block-like feeling of most rain boots, the Totes Cirrus sheds some weight while shedding sheets of rain. They’re thinner and a lot lighter than most other options. Because of that, they’re super flexible and can even collapse, should you need to pack them in your suitcase for your flight to Seattle.
The Best Not-Quite Rain Boot
If you want sturdy, waterproof boots that aren’t full-on rubber rain boots, this is your move. Timberland’s premium seam-sealed waterproof boot gives off classic work boot energy without any of the stiffness of a rubber rain boot. Their classic workwear style pairs well with just about anything, too, whether you’re gettin’ work done in double-knee carpenter pants or putting on some nice trousers for a date.
