Shoes | January 5, 2023 9:58 am

22 On-Sale Winter Boots to Get You Through the Slushiest Season

Which one will you choose?

a collage of winter boots on sale on an icy background
No need to wait for deals and steals on cold-weather footwear: the best winter boots for men are already on sale.
Getty Images

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

With unseasonably warm temps keeping cold weather at bay — New York City, for instance, sat at a balmy 64 degrees yesterday — you might think that there’s no possible way that the winter boots (or jackets) you’ll most certainly need come two-weeks time could possibly be on sale. Welp, read that big, bold, beautiful headline and weep. That’s right: because we’re always hounding for a deal and because we’re also going to need a pair soon enough, we’ve spent copious hours researching, tracking down, and compiling a load (22, to be exact) pairs of the best winter boots currently on sale.

We’d be remiss not to point out that it’s not just snow shoes and duck boots we’re talking about here: all this sick winterized footwear comes in many shapes and sizes. Sleek Chelseas for the weekday warrior, hefty work boots for the blue-collar chap, technical hikers for the Gorpcore-obsessed, even cozy slippers for the indoor enthusiasts. No matter what tribe of winter boots you prescribe to, chances are you, you can find a quality pair below, on sale no less.

Don’t be dissuaded by your current lack of need — we can all but guarantee that dreary, slushy weather will indeed reveal itself, and these deals won’t last forever, so better safe than sorry, eh? (Hint: a solid pair of kicks make for a very good way to spend that hard-earned holiday cash.) From Blundstone to Salomon to UGG and beyond, the best on-sale winter boots for men.

Blundstone Original 500 Chelsea Boot
Blundstone Original 500 Chelsea Boot

You know them, you love them and if you don’t already have them (or just need a new pair) Blundstone’s ultra-versatile Original 500 Boot is currently 22% off at Amazon.

Salomon X Ultra Pioneer Mid Waterproof Hiking Boot
Salomon X Ultra Pioneer Mid Waterproof Hiking Boot

Salomon makes some of the best technical boots money can buy, and regardless of whether you’re hitting the trails or flexing with your Arc’teryx, these X Ultra Pioneer’s will crush winter’s worst.

J.Crew MacAlister Shearling-Lined Suede Boots
J.Crew MacAlister Shearling-Lined Suede Boots

No one has to know that your sharp suede MacAlister’s are fleece lined. No one.

Hoka Kaha GTX
Hoka Kaha GTX

Not ready to give up your sneakers just yet? Hoka’s maxed-out Kaha has a Gore-Tex coating and yards of cloud-esque foam for that perfect cushioned feel.

Allen Edmonds Wren Leather Lug Chelsea Boot
Allen Edmonds Wren Leather Lug Chelsea Boot

Need to look you best, but the weather isn’t cooperating? Allen Edmonds to the rescue, with a dressy Chelsea that’ll power you through inclement weather and board meetings alike.

Fracap M170 Comando Sole Boot
Fracap M170 Comando Sole Boot

Italian hertiage bootmakers Fracap really said leopard print on the commando.

Wolverine Loader 8″ Wedge Soft Toe Boot
Wolverine Loader 8″ Wedge Soft Toe Boot

Wolverine’s Loader Boots are the go to for lumberjacks and hipsters everywhere. Which are you?

UGG Neumel Snapboot Chukka Slipper
UGG Neumel Snapboot Chukka Slipper

We thought UGG was inventive when they Frankensteined the classic Chukka and the cozy slipper into one sweet bootie, but freaking it in an electric blue is another level entirely.

Cole Haan ZeroGrand Waterproof Chukka Boot
Cole Haan ZeroGrand Waterproof Chukka Boot

Although Cole Haan’s styles are a dime a dozen at most corperate offices, we’ll admit that there’s some appeal to the waterproofing ZeroGrand tech that these Chukkas sport.

Rhodes Roper Boot
Rhodes Roper Boot

It’s never been easier to cosplay as a cowboy in the dead of Montana’s winter than with some beat up denim, sherpa-line trucker jacket and these bad boys.

Suicoke BOWER-Evab Boots
Suicoke BOWER-Evab Boots

Suicoke’s futuristic stompers make light work of a couple feet of snow.

Timberland 6″ Premium Waterproof Work Boot
Timberland 6″ Premium Waterproof Work Boot

You don’t need to live in New York to have a real “Hey, I’m walking here!” moment.

Merrell Moab 2 Mid Waterproof Hiking Boots
Merrell Moab 2 Mid Waterproof Hiking Boots

The Merrell Moab is universally considered some of the best winter footwear around, and for good reason — precociously calculated tech, an impenetrable seal and Vibram TC5+ sole make sure you stay stable and dry when you need it most.

Hunter Original Chelsea Boots
Hunter Original Chelsea Boots

Don’t miss out on this one: Hunter’s iconic boot rarely hits sale.

Dr. Martens 101 Suede Ankle Boots
Dr. Martens 101 Suede Ankle Boots

Great for hopping through slush. Equally great for kicking in teeth at the hardcore show.

Adidas Terrex Hiker 2 Hiking Boot
Adidas Terrex Hiker 2 Hiking Boot

Adidas’ second iteration of the Terrex Hiker improves on the already excellent design, with a lockdown collar and added protection from virtually all the elements.

Sperry Brewster Waterproof Duck Boot
Sperry Brewster Waterproof Duck Boot

Move over, Bean Boot, there’s a new Brewester in town.

Eddie Bauer K-6 Boot
Eddie Bauer K-6 Boot

We’ve said it before and we’ll say it again — with Goodyear welt, premium leather and a Vibram sole, the value-to-cost ratio on Eddie Bauer’s K-6 Boot is virtually unbeatable.

Polo Ralph Lauren Olso Chelsea Boots
Polo Ralph Lauren Olso Chelsea Boots

Mr. Lauren’s Olso Boots are like a fine mullet: business as usual on top, snow-stomping party on the bottom.

Diemme Onè Hiking Boot
Diemme Onè Hiking Boot

Half hiking boot and half monster truck, DIemme’s treaded Onè won’t just keep those tootsies warm and dry: it’ll ensure all eye are on you.

Converse Chuck Taylor All Star Lugged 2.0 Counter Climate
Converse Chuck Taylor All Star Lugged 2.0 Counter Climate

For the sneakerhead who just can’t be asked to give up his kicks, these puddle-crushing, lug-soled Converse All Stars make a healthy compromise.

Clarks Wallabee Gore-Tex Booties
Clarks Wallabee Gore-Tex Booties

Is Clarks Wallabee technically a boot? Jury’s out, but with a resistant Gore-Tex shell and mrudered-out colorway, we let it slip through the cracks.