20 Best Winter Boots to Keep Your Tootsies Toasty

When the weather outside is frightful, keep your feet feeling delightful. We have 20 fashionably fantastic boots for cold, rain, sleet and snow.

The days are getting shorter and the weather is getting cooler. Plenty of us are seeing rain, sleet and snow already, which means it’s time to break out those boots!

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At SLHer, we love a good boot. And this season, there are so many fun and fashionable choices, across a variety of price points, that you’re going to adore.

Here are 20 (count ’em!) fantastic finds from our Editors…

COLD FALL FUN

No precipitation but just plain cold? These boots were made for walking…fashionably of course.

From pumpkin patching to running errands, these western style booties are the stylish addition you need for your fall wardrobe.

The Kooples, Low Ankle Boots w/Straps $204.05

(on Sale NOW from $385)

Yes indeedy, the slouchy boot is back for winter ’22. Pick up a pair in some moody fall colors, like this olive toned version, that will go so well with all your dark florals.

Boston Proper, Suede Slouchy Boot $129.99

(on Sale NOW from $159)

Classic lace-up meets après ski-artisan in this shearling boot. It’s like a snuggly cardigan for your feet.

Beek, Alpine Swift Shearling Bootie $395

All the sturdy footing of a chunky hiking boot with a 2.5″ heel? Exactly. And we even like the color!

Dolce Vita, Haloe Canvas Boot $89.99

(on Sale NOW from $140)

Talk about oldie but goodies, sales for the Wallabee by Clarks have spiked this season. Of course once you try a pair on, you’ll know immediately why these moccasin-meets-boots have been favorites for over half a century.

Clarks, Wallabee Hi Warmlined Suede $220

 

WHEN IT RAINS, IT POURS

“Singing in the rain” may be a heart warming classic, but soggy feet is a nasty tune. These boots will keep your feet happy and dry as you navigate your way through those perilous puddles.

Outside may be gray, but these colorful plaid booties will give you happy sunshine vibes all day.

Circus by Sam Edelman, Darielle Boot $100

In the battle to keep your feet dry, these combat booties from rag & bone are ready to get into the field.

rag & bone, Shiloh Rain Boot $225

When the puddles are deep and the ground is slippery, you want a tall rain boot with superior grip. This one from Burberry delivers all of the above and in that classic BB plaid.

Burberry, Vintage Check Rubber Rain Boot $493.99

(on Sale NOW from $790)

For those times when you need to just throw something on quickly for a short jaunt. These rain shoes have all the waterproofing you need in an easy on/easy off sneaker style.

Joules, Rainwell Short Height Slip-on Wellies $69.95

Finally, who says you can’t have a solid rain boot that doesn’t look like a rain boot? Not us, and certainly not the folks at the Chloé brand…

Chloé, Betty Rain Boot $269.99

 

BEAT THE SLEET

Whether it’s rainy days that turn into freezing cold, or those just-warm-enough days that turn all the snow into slush, you know you’re going to be dealing with Sleet. Probably the least popular of precipitations, your choice of boots need to be both water-resistant and warm. Here’s some of our Editors’ favorites for keeping you grounded and comfortable.

21st tech meets handsome classic style in this slip on boot by LaCrosse. Inside is super soft microfleece and outside is all business, with waterproof shell bottom and premium rubber soles for stability on those icy patches.

LaCrosse, Aero Timber Slip-on Boot $112.46

(on Sale NOW from $146)

The Sorel brand is synonymous with quality hiking shoes and boots. This weatherproof nylon boot called the Explorer Carnival takes their function-first philosophy and gives a streetwear spin to it.

Sorel, Explorer Carnival Weatherproof Nylon Boot $109.99

(on Sale NOW from $145)

Sperry is another iconic brand when it comes to cold and wet weather boots. These grippy, rubber soled waterproof boots prove that you can still have an anti-slip shoe and your heel too. Bonus – they’re salt water stain resistant (perfect for navigating those just salted sidewalks).

Sperry, Saltwater Heel Leather & Rubber Boot $79.99

(on Sale NOW from $140)

For when your outdoor errands have you standing on your feet for a while, these snuggly warm and water resistant boots by Muk Luks have a memory foam insole to stave off any foot fatigue.

Muk Luks, Bridgehampton Boot $84.99

Finally, when the path is more ice than water, this pull-on, waterproof boot from Keen will help keep you firmly on terra firma. In addition to the grippy sole, the Betty has nylon shanks for reinforcing your balance by keeping your stance rigid. So you can leave the ice skating for the professionals.

KEEN, Betty Pull-on Waterproof Boot $138.71

(on Sale NOW from $184.95)

 

LET IT SNOW, LET IT SNOW

Powder, flakes, dust, we have a lot of names for snow. When it’s fresh and covering the world like a blanket, it can look absolutely beautiful. But navigating through it without some proper footwear and winter wonderland will be the last thing on your mind.

When you’re just out for a quick point A to point B and want to arrive without wet feet, this low top, quilted bootie from Cole Haan is exactly what you need. Lace up closures help keep that faux shearling inside all warm and snuggly.

Cole Haan, Generation Zerogrand $64.99

(on Sale NOW from $130)

Looking for something truly original? Few winter boots can rival the iconic silhouette of the Moon Boot. The playfulness-meets-practicality of these astronaut inspired boots have been drawing attention since their invention in the late 70s. This version is a collab between Moon Boot and the Milan based, folk-chic brand of Alanui. It actually comes in a few color options, but why go for the docile neutral colors when you can be front and center in acid lime green.

Alanui x Moonboot, Bandana Print Boots $550

Leave it to the Italian house of Aquatalia to design a winter combat boot that looks effortlessly chic. These autumnal wine versions will go with just about anything in your wardrobe.

Aquatalia, Alyssa Suede & Shearling Boot $255.99

(on Sale NOW from $575)

When the temperature outside is hitting negative double-digits, you need a boot that can maximize your foot’s body heat. Made of Primaloft (synthetic microfiber developed for the military for cold weather clothes) these high top boots by adidas also come with the patented high-traction outsole of the Terrex brand.

adidas, Terrex Cold.Rdy Boots $140

Finally, when you’re dealing with seriously deep snow drifts, it can be challenging to keep those icy flakes from sneaking their way from up top and down into your feet. Not only are these winter boots from Baffin a good mid-calf high, the top of the boot has a quick, draw cord to keep out any uninvited guests.

Baffin, Escalate Boot $149.95

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