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  4. The 10 Cutest Boots for Chilly Days Ahead

The 10 Cutest Boots for Chilly Days Ahead

By Laura Reilly
Updated Sep 20, 2019 @ 1:00 pm
Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
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We hate to break it to you, folks, but it’s about that time. Strappy, barely there sandals are no longer the reigning class of our shoe racks. It’s warm winter boot season, and this year there are a lot of exciting styles to try on for size.

We surveyed the landscape of women’s winter boots, and noticed a few distinct trends. There’s the athleisure influence, for one, which has tugged combat boots and padded booties in the direction of sneakers. (You can thank athleisure for the stylish added tread at the base of your boots this year.)

Another theme that cropped up again and again was actually a step backward rather than forward. Both high-end and affordable brands borrowed details from vintage styles for their snow boots this year, with the 1910s and 1970s being some of the most-sourced decades — think national park advocates and Everest explorers.

These are the best women’s snow boots and waterproof boots to buy in 2019:

Best Sorel: Kinetic Short Booties Best North Face: Back to Berkeley Redux Waterproof Bootie Best Columbia: Ice Maiden II Insulated Snow Boot Best L.L. Bean: Signature Retro Colorblock Waxed-Canvas Bean Boots Best Timberland: Sienna High Leather Combat Boots Best Moncler: Ginette Knit Cuff Leather Rain Boot Best Coach: Portia Cold Weather Bootie Best Splendid: Potter Combat Boots Best No.6: Pull On Shearling Boots Best Rag & Bone: Compass Genuine Shearling Combat BootRead on to see why each of these made our top list.

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Best Sorel: Kinetic Short Booties

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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

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Best Columbia: Ice Maiden II Insulated Snow Boot

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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

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Best North Face: Back to Berkeley Redux Waterproof Bootie

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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

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Best L.L. Bean: Signature Retro Colorblock Waxed-Canvas Bean Boots

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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

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Best Timberland: Sienna High Leather Combat Boots

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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

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Best Moncler: Ginette Knit Cuff Leather Rain Boot

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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

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Best Coach: Portia Cold Weather Bootie

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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

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Best Rag & Bone: Compass Genuine Shearling Combat Boot

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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

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Best Splendid: Potter Combat Boots

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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

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Best No.6: Pull On Shearling Boots

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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

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Everything in This Slideshow

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1 of 10 Best Sorel: Kinetic Short Booties
2 of 10 Best Columbia: Ice Maiden II Insulated Snow Boot
3 of 10 Best North Face: Back to Berkeley Redux Waterproof Bootie
4 of 10 Best L.L. Bean: Signature Retro Colorblock Waxed-Canvas Bean Boots
5 of 10 Best Timberland: Sienna High Leather Combat Boots
6 of 10 Best Moncler: Ginette Knit Cuff Leather Rain Boot
7 of 10 Best Coach: Portia Cold Weather Bootie
8 of 10 Best Rag & Bone: Compass Genuine Shearling Combat Boot
9 of 10 Best Splendid: Potter Combat Boots
10 of 10 Best No.6: Pull On Shearling Boots

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The 10 Cutest Boots for Chilly Days Ahead
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