14 Waterproof Boot Picks For Winter’s Worst Snow, Slush, and Rain

14 Waterproof Boot Picks For Winter’s Worst Snow, Slush, and Rain
Waterproof boots are more functional and stylish than ever before.

Winter arrived several weeks ago, and depending on where you live, you may or may not have noticed. But things could get very dicey in the coming weeks. Winter often saves its worst for February because it loves to lull you into a false sense of early spring before it kicks you in the teeth. Days with highs of 60 smashed the next day with temperatures in the teens.

In fact, almost 75% of snowstorms attaining a category 3 or higher between 1956 and 2019 occurred in late January or February.

When winter unleashes its worst, three-season footwear just won’t cut it. But having the right winter boots can make the difference between having damp socks for hours and staying dry and comfy even after you’ve trudged through snow, slush, and water.

Of course, choosing the right winter boots isn’t always simple.

Not all boots are created equal and not every winter boot has to make you look like you’re mushing sled dogs. Thanks to modern materials, you can head out in dressier waterproof boots and just give them a quick stomp and wipe without having to change when you get there.

If your style is casual, but you still want to look put together you can even opt for more of a leather hiker with slim slacks, a solid flannel shirt, and a casual blazer. If you’re spending most of your time outside, then opt for waterproof work boots or insulated duck boots. Whatever your style druthers are, there’s a great winter boot out there for you to thrive this season instead of just survive. Here are fourteen of our favorites.

XTRATUF 6″ Legacy Lace ($150)

huckberry mens legacy lace winter boot

One look at the Legacy’s thick rubber outsole, and you know it’s ready to take on winter. It also happens to be an unofficial favorite of Alaskan fishermen who need wet and cold weather protection with high traction. But don’t discount its rugged style thanks to soft leather uppers and meticulous stitching. Its waterproof construction means it’ll take on sleet, rain, and wet snow with ease, while the twin pull tabs make for easy ingress and egress for men in a rush.

Sorel Madson ($118)

sorel madson waterproof bootFor all the comfort of a sneaker–minus the sogginess–try this boot on for size. Available in four colors and two leather options (full-grain or suede), the Madson is an ideal blend of high performance and low-key good looks. So much so that you'll probably find yourself reaching for them even on sunny days. Sorel has almost 60 years of experience in the shoe biz, and it shows.

Danner Jag ($117+)

danner jag waterproof winter boot

If you’re more of a sneaker guy than a Red Wing guy, the Jag is your winter boot. The Jag might look like a casual day hiker, but it’s so much more. The leather and textile combination is actually totally waterproof via Danner Dry treatment while the old school style quotient remains high. Not only is it a comfortable everyday boot with well-cushioned OrthoLite footbed, but it can also manage winter slickness with a high traction waffle sole. This is one boot that’s just about perfect for the casual office, too.

Sperry Top-Sider Avenue Duck Boot Chukka Boot ($68+)

sperry avenue duck chukka winter boot

Duck boots can make you look like you’re only planning on going to the farmer’s market to pick up the goods for making clam chowder, but not these. The Avenue Duck Boots eschew the doughy look of standard duck boots and replaces them with rich, dark leather and a more masculine Wellington toe with a pronounced edge. They’re totally waterproof and seam-sealed with a thermal lining throughout for less than savory temps and conditions.

Carhartt Men's 6-Inch Waterproof Wedge Soft Toe Work Boot ($131)

carhartt soft toe work winter boot

Just because these are rough and tumble work boots doesn’t mean you can’t play in them. The fully waterproof wedge boots are just what you need for casual style while imparting winter toughness to your feet. The tall tongue makes them easy to put on, and the contrast stitching on four rich colors adds a touch of flair. They’ll take on hours of outdoor work without making your dogs ache, but they’ll also look pretty sweet at the bar during Happy Hour with any one of these great waxed jackets.

Kamik Icebreaker Cold Weather Boot ($65)

kamik icebreaker cold weather winter boot

Wellies aren’t just for wet weather. If properly constructed like these Kamiks, they can get you through dropping temps and blizzards, too. The Icebreakers are made of flexible 100% natural rubber and extend 13 inches, so deep snow is no match. It’s also lined for warmth, and the cloth cuff cinches to keep out the bad stuff. What’s more, you might actually get mistaken for a stylish British chap as you trudge through winter’s worst.

Merrell Ontario Thermo Mid Waterproof ($200)

merrell ontario waterproof winter boot

Here are another pair of old-school-style hikers that are perfect for casual winter style. The Ontario’s can also back things up with true waterproofing and even salt resistance, as well as a merino wool and fleece lining to keep you cozy while looking tough, at the same time. The Vibram Arctic Grip sole manages ice and packed snow with supreme traction, and the thick full leather upper continues into a bellows tongue that keeps the nasty stuff out.

Clark’s Tilden Waterproof Ankle Boot ($92+)

clarks tilden ankle winter boot

If you happen to wear clumsy and goofy-looking rubber shoe covers over your dress oxfords in the winter, it’s time to lose ‘em and fast. The Tildens look every bit as good as a fine pair of dress boots can and also provide waterproof full grain leather to dispel snow and slush. They’re also five inches tall to prevent sock wetness when you walk through the white stuff. The Tildens will mate perfectly with a suit or slim dark jeans alike.

The North Face Men's Chilkat IV Insulated Boot ($115)

mens north face chilkat IV winter boot

If you need a winter boot that knows its job and does it well, the Chilkat IV from The North Face will have you crunching through thick, wet snow with ease. The bottom half is covered with a TNF rubber outsole featuring icepick lugs to ensure you stay vertical when Mother Nature throws everything she's got at you.

KEEN San Jose 6” Waterproof Work Boot ($160)

keen san jose work winter boot

KEENs can take a beating, but you don’t have to get a pair with their signature massive rubber toe in order to weather the elements. The San Jose boots look like slightly fancier wedge work boots, which they are, but they’re also meant for winter’s worst with their waterproof and breathable membrane that keeps the elements out and dispels perspiration so your feet stay fresh. Hell, the soles even have sipes like winter tires to push water and slush out for increased sure-footedness. Pair them with some of these jeans for great workwear style.

Cole Haan Men's Zerogrand Chelsea Waterproof Boot ($200)

cole haan zerogrand chelsea winter boot

If you want fancy and fleet-of-foot wrapped in a winter boot, the Zerogrand Chelseas are perfect. If you lean towards slightly trendy in your personal style palette, they’re a good fit for both dress and weekends. Half sneaker and half dress boot, they’re ready for snowy sprints and office meetings, too. The spongy rubber sole is cushy, and the rubber pods on the outsole provide wet-weather grip. The soft leather is deceiving since it both cradles your feet and keeps water and slush out, so no one rains on your parade.

LLBean East Point Waterproof Boot ($149)

llbean waterproof boots

If you're more of a “buy one pair for any conditions” kind of boot guy, the waterproof East Point from LLBean is your best choice. A classic silhouette with a lugged sole and cap-toe, these boots can easily be worn dressed down or in a more rugged, smart casual kind of way.

Columbia Fairbanks Omni-Heat Hiking Shoe ($110)

gray columbia winter boot

Don't let the name fool you, these hikers are rated to -25 degrees Fahrenheit and have a seam-sealed waterproof membrane. These things are just as comfortable as your bedroom slippers – an appreciated luxury when you're forced out of bed early to shovel the driveway before work.

Timberland Kendrick Waterproof Chukkas ($160)

black timberland bootThese handsome chukkas may share a soul (and a sole) with the classic work boot that made Timberland a street style staple, but the stripped-down, even sophisticated silhouette belies their rugged roots. Waterproof membranes and full-grain leather uppers keep your feet snug and dry, and sturdy rubber lug outsoles will keep you from faceplanting in the sleet or snow. The Kendrick also doesn't scream “snow boot,” so there's no need to swap them out for dress shoes at the office.

Amos Kwon

Amos is an aficionado of cars, cigars, watches, whisky, tech, and style. He's written for Gear Patrol, Askmen, Inside Hook, and Fatherly. He's based in the Chicago area and lives with his wife and three children. Follow him on Instagram @wrathofkwon.