The 10 Cutest Boots for Chilly Days Ahead

These snow boots have sneaker in their DNA, and the look is really working for us. A wavy rubber sole lends a streetwear energy, and a tan upper makes us feel all warm and hygge inside. Beyond pure aesthetics though, these boots check off all of our key performance boxes: excellent grip, ample insulation, and a side zip for easily sliding on and off.

Shop now: $140; shopbop.com

If serious protection is your goal, look no further than these full-coverage, leather and textile insulated boots from Columbia. These heavy duty boots have a nine-inch shaft, and provide a hefty layer of insulation without adding on superlative weight. You can also feel confident walking on icy surfaces, thanks to the Omni-Grip outsole.

Shop now: $69–$164; amazon.com

This lace-up high top shoe isn’t just good for the hiking profile it embodies, it’s also a great everyday shoe during the cooler months. Pairing a waterproof shell with North Face’s proprietary PrimaLoft® insulation and compression-molded EVA midsole, this retro reissue will keep you dry, warm, and supremely comfortable.

Shop now: $130; nordstrom.com

This year, we’re all about brands digging into the archives and reissuing some of their most iconic looks with updated technology. This patchwork throwback style by L.L. Bean is no exception — our number one source for impeccably made duck boots has re-released a jazzy old boot first launched in 1912. Its 10-inch shaft made of waxed canvas and rubber will keep you dry with a side of style all season long.

Shop now: $139 (Originally $179); llbean.com

Try a classic style with a twist this season, perhaps with this pair of lightly lifted Timberland combat boots. The 2.5-inch pitch will add some height, but remain at a comfortable level for walking, even across more challenging terrains (we see you, sludgy parking lot).

Shop now: $190; saksfifthavenue.com

For days when it's wet and chilly, but not frostbite-cold, a sleek, water-resistant Wellington boot with a knit foldover cuff will suffice. This monochrome pair by Moncler was made in Italy of wool and rubber, and is available in black or blush.

Shop now: $360; nordstrom.com

If you love UGGs but hate soggy suede, consider these fluffy, cozy Coach boots with rubberized soles. A shearling body cradles your lower leg and foot like an apre-ski dream, while a performance base makes it safe and comfortable to actually venture outdoors.

Shop now: $113 (Originally $225); coach.com

While not actually a heritage brand itself, Rag & Bone has taken the throwback trend to heart by fashioning its own retro-inspired boot. This shearling-trimmed combat boot draws inspiration from classic hiking styles, but provide advanced footwear technology like lugged Vibram® rubber soles for a safe tread.

Shop now: $695; nordstrom.com

As roads begin to get icier, it's important to protect yourself from unexpected tumbles. The plush cushioning on this pair by Splendid offers excellent ankle support, plus great cradling for your arches. Shortly put: These boots were made for walking (in any weather).

Shop now: $198; shopbop.com

If you’re ready for low temps, but not ready to give up on “fashun” altogether, might we suggest these extremely cool clog boots? Tell the world you shop organic while also being able to leave your house without losing a toe to frostbite. Plus, enjoy the advantage of a rubber sole, otherwise missing from some of No6’s more summer-y styles.

Shop now: $390; shopbop.com