Shoes | December 28, 2021 8:11 am

The Best Winter Footwear for Plodding Through Rain, Snow and Other Crappy Conditions

Footwear built to put those old galoshes to shame

The Best Winter Footwear for Plodding Through Rain, Snow and Other Crappy Conditions

Nota bene: If you buy through the links in this article, we may earn a small share of the profits.

The best winter-proof shoes are certainly weatherproof and most likely insulated; whether lugged or grooved, they have a stable base for anti-slippage. Leather, hard polyester and rubberized material are the general culprits for uppers. And we’d be remiss not to mention that winterized footwear comes in many forms; a chelsea boot, a hiker, even running shoes are all viable options, if done right.

So we’ve picked some of our favorite styles to rock during the winter, all of which will keep them tootsies warm and comfortable. Maybe a well-designed moccasin is all you need, or maybe an all-out affair of sherpa lining and treads is required. Whatever best suits you and your local weather, we’re positive we have a pair for you.

Hunter Boots

Hunter Insulated Chelsea Boot

Hunter is more or less synonymous with rain boots at this point, with their iconic red-square logo a beacon for all those looking to stay warm and dry. The Insulated Chelsea does an especially good job of that; tested to temperatures of 23°F, it’s one of your best options for winter footwear.


Timberland Premium 6-Inch Waterproof Boot

The iconic winter boot, the Timber Premium has built a legacy for a reason; quality leather, waterproof upper, lug sole, and tons of curb appeal.

L.L. Bean

L.L. Bean Bean Boot Moc

As we’ve previously stated, these are the perfect shoe for cosplaying as a lobster fisherman from Maine.


Blundstone Original #500 Boot

The Aussie-made Blundstone has quickly become a go-to boot: sturdy, stylish and ready to take a beating, they can handle virtually anything thrown at them. 


Hoka Speedgoat 4 GORE-TEX 

Weatherproof footwear doesn’t have to mean stuffy boots, as evidenced by Hoka’s Speedgoat 4. The Gore-Tex-equipped trail runner is fully weatherproof and ready to take on mountain pass as slushy subway alike.


Sorel Conquest Boot 

There’s the promise of dryness, and then there’s the Conquest Boot.


Sperry Cold Bay Duck Boots 

Another classic heritage brand, Sperry’s dabbing in the duck boot style has produced some exceptional results. The Cold Bay Boot is insulated with a microfleece “thinsulate” lining that keeps in heat and blocks cold.


UGG Classic Mini Boot

Okay, okay, there’s are not technically weatherproof, but we like our UGG boots salt-rimmed and beat up anyways. Plus, with all that internal shearling, your foot is going to stay dry regardless.


Huckberry x XtraTuf Deck Boot

A neoprene boot a day keeps the weather at bay.

Todd Synder

Danner Mountain Light Hiking Boot 

Danner’s best-in-class hiking boots are weatherproof, for sure, but the trekkers happen to mean your everyday commuters needs quite well, too.


Merrell Jungle Moc Crafted Cozy 

You put your left foot in, you put your right foot in, and poof. Instant comfort.

End. Clothing

Common Projects Winter Chelsea Boot 

The CP Winter Boot is everything you love about a regular Chelsea, upgraded and winterized.

Aether Apparel

Aether Apparel Dolomite Boot

The Dolomite Boot from Aether Apparel and Fracap might just be the most handsome boot on the market right now. Full-grain leather, contrast lacing, and and a rugged sole all make this hiker well worth the daunting price tag.