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!

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.

Windsor, Studded Chic Fold-Over Under-The-Knee Boots

$52.90

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

Hey Dude, Reyes Suede Tan $94.99

Yes indeedy, the mock-croc boot is back for winter ’24. Pick up a pair in some moody fall colors, like this chocolatey toned version, that will go so well with all your autumnal outfits.

Windsor, Chic Moment Faux Leather Croc-Embossed Under the Knee Boot $44.90

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

Palladium Boots, Pallabase Leather $126

(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. We’re loving this version of the original in on-trend olive green.

Clarks, Wallabee Boot in Green Suede $160

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 delightful dark cherry booties will give you happy sunshine vibes all day.

Journee Collection, Waterproof Drip Rain Boots $54.99

(on Sale NOW from $99.99)

Not a superfan of the stiff rubber feel? These beauties are soft, supple and still completely waterproof.

Easy Street, Frazer Waterproof Mid-Calf Boots $51.99

(on Sale NOW from $79.99)

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.

Bogs, Amanda II Tall Rain Boot $89.99

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 slip on style.

Bogs, Kicker Chelsea Rain Boot $80

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 $399.99

(on Sale NOW from $550)

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 $97.47

(on Sale NOW from $149.95)

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

Sorel, Explorer Next Weatherproof Suede Boot $95.99

(on Sale NOW from $155)

G.H. Bass 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 cozy comfort too. Bonus – the rubber portion is salt water stain resistant (perfect for navigating those just salted sidewalks).

G.H. Bass, Duclair Waterproof Duck Boot $59.99

(on Sale NOW from $145)

For when your outdoor errands have you standing on your feet for a while, these snuggly warm and water resistant boots by The North Face have a super cushy insole to stave off any foot fatigue.

The North Face, Sierra Mid Lace Waterproof Boot $149

Finally, when the path is more ice than water, this quick-lace, 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 Short Waterproof Boot $71.44

(on Sale NOW from $199.95

 

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, waterproof bootie is exactly what you need. Easy slip on design helps keep that faux shearling inside all warm and snuggly, and bonus, it’s made of quick dry material so by the time you’re ready to head back out, they’ll be dry.

Easy Street, Flurry Easy Dry Waterproof Boots $51.99

(on Sale NOW from $79.99

Looking for something truly original? These breathable, waterproof GORE-TEX® winter hike boots are a collab between sportwear brand adidas and Stella McCartney. Designed for long distances and unpredictable weather, they’re super insulated to keep your tootsies toasty for hours. All this with a look that’s undeniably stylish, and it’s made from 20% recycled materials.

adidas x Stella McCartney, Terrex Free Hiker Gore-Tex Boots

$300

Leave it to the LA brand Seychelles to design a winter boot that looks effortlessly chic. This nicely neutral version will go with just about anything in your wardrobe.

Seychelles, From The Start Leather Boot $54.99

(on Sale NOW from $179)

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 $164.95

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