15 Best Men’s Rain Boots in 2021: Hunter, L.L.Bean, Timberland, and More

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. 

Best Overall Rain Boot

Xtratuf Legacy Chelsea 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 Fashion Flex Rain Boot

Bottega Veneta Puddle Chelsea boots

Bottega Veneta is on a winning streak under the creative direction of Daniel Lee, churning out head-turning pieces like these bulbous puddle boots. In addition to the modern shape, they’re made from a biodegradable natural rubber material and come in a range of vivid colors. Wear them when you feel like dripping harder than the rain.

The 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 Most Iconic Rain Boot

Hunter Original tall 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.

Best Budget Rain Boot

Totes Cirrus ankle rubber 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.

Best Non-Rain Boot Rain Boot

Timberland 6″ premium waterproof 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.

9 More Rain Boots We Love

Tingley high top stretch overshoe

When you absolutely refuse to get another pair of shoes or let go of your sneakers, you can opt for some rubber overshoes like these. Simply slip them on to your favorite shoes and boom—instant protection. 

Plasticana hemp wellies

While other rain shoes typically use rubber, leather, and neoprene, Plasticana’s wellies are made from a fully-recyclable and natural rubber derived from hemp. The speckled look comes from the hemp itself and gives the boots a unique texture. 

Muck Boot Company muck chore boot

If you need your rain boots to also be mud boots, these can take on the gunk with ease. The beefy outsole tread pushes through mud easily while the thick layered toe provides protection. 

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Bogs classic mid waterproof insulated boot

When the bitter cold gets even more bitter, these insulated boots will keep your blood flowing through freezing rain and harsh snow, down to -40F.

Xtratuf deck boot

These short rain boots have a lot of the advantages of the Chelsea (mentioned above) but with some city-friendly sneaker styling. The added neoprene collar also helps keep your feet and ankles dry and comfortable.

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Hunter Original Refined waterproof Chelsea boot

Hunter’s Chelsea is sleeker and dressier than its Original Boot, making it perfect to pair with slim jeans or a suit. And because it’s a shorter style, it’s great for when the rain is bearable and not blowing at you horizontally.

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Salomon X Ultra 3 GTX Mid boots

When you’d rather not have your rain boots look like, well, rain boots, Salomon’s gorp-tastic boots will give you all the water protection you need and none of the rubber you don’t.

Sorel 1964 LTR tall boot

A bit more refined the the bulbous L.L. Bean boot, and equipped with insulation just in case you need your rain boots to also be snow boots.