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The Best Tall Boots to Stay Warm and Look Stylish this Winter

When it comes to cold-weather investment items, a pair of tall boots ranks just below a winter coat. Considering how heavily you rely on tall boots day after day as an essential element of your outfit, they’re easily the single most important shoe accessory in your winter wardrobe. They’re also ultra-practical for staying warm, so you can brave brutal weather in style. You’ll want to start with a staple pair in a neutral color, ideally made of leather with a low wedge or stacked heel. Beyond that, go for something that makes a statement to give your look a lift when those gray-sky days get you down. Read on for our top tall boot picks—and outfit inspiration on how to rock them. 

1

Best Tall Boots

Everlane The Knee-High Boot.

The Knee-High Boot

With quality 100 percent Italian leather, a cushioned insole, and classic silhouette, these Everlane tall boots are a no-brainer. The slightly rounded pointy toe and slouchy vibe elevate the otherwise casual look and sensible two-inch heel. If you already have a staple pair of brown boots, go for the winter-worthy bone color. 

 

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2

Best Over-The-Knee Boots

Stuart Weitzman The 5050 Boot.

Stuart Weitzman The 5050 Boot

Over-the-knee boots are as chic as they are practical (like adding a second pair of pants). Live your best life and wear them with leggings for weekend farmers market strolling, or slip them over a pair of tights to coordinate with a mini skirt. Also, they’re from Stuart Weitzman, so expect ultra supple leather and quality that’ll last years. 

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3

Best Steve Madden Knee High Boots

Steve Madden INTYCE BLACK LEATHER.

Steve Madden Intyce 

Fans of the Steve Madden brand report buying these tall boots season after season. They’re one of the brand’s best-sellers, and we can see why. They have a low wedge—great for getting height and trudging through snow—and a generously wide shaft to tuck in jeans or sweater leggings, and durable construction. Bonus points for being super easy to pull on and off.

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4

Best Waterproof Over-The-Knee Boots

La Canadienne Scarlit.

La Canadienne Scarlit

La Canadienne is based in Montreal, so their designers certainly know a thing or two about making boots that are waterproof and can hold up to snowy winters. What makes these next level is their style—totally polished and work appropriate. Win win! 

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5

Best Equestrian Tall Boots

FRYE Women's Valerie Shearling Over-The-Knee Riding Boot.

FRYE Women’s Valerie Shearling Over-The-Knee Riding Boot

These tall boots are the coziest pair in our roundup, with a wide shearling cuff that can be folded up as a muffler for your knees. They’re also brilliant in the snow, thanks to a thick rubber sole with deep treads. For a sleeker look, go with the black pair; the cognac and antique dark brown are more rustic-chic. 

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6

Best Designer Tall Boots

We get major mod ’60s vibes from these Marc Jacobs boots, with a wide, flared block heel just shy of 4 inches high, and a squared-off toe. They hit just under the knee, and have subtle contrast stitching details. Rock them at on New Years Eve with your LBD and sheer, patterned black stockings. 
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7

Best Tall Boots for Wide Calves

LULEY WIDE CALF OVER THE KNEE BOOT.

Marc Fisher Luley Boot

Finding a pair of dressy, wide-calf boots that look expensive despite being made from stretchy material can be a challenge. But this chic pair from Marc Fisher hits the mark. They’re faux suede, with a partial inside zipper to keep them streamline, and a flattering deep V in back with a hidden piece of elastic. That sparkly holiday mini-dress just found its match. 

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8

Best Frye Tall Boots

Frye Women Veronica Slouch Boots.

Veronica Slouch

There are some tall boots that look better the more you beat them up, and this pair from Frye falls into that category. They’re constructed of rugged, washed oiled leather, have a rubber lug sole, and moto-chic antique metal hardware. You’d be surprised at how well they can pair with breezy chiffon floral dress. 
 
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9

Best Tall Combat Boots

These boots are as badass as they come—and you can count on staying toasty in them, too. They’re made from thick full-grain leather, with a cushioned sock lining the 17-inch shaft. They also have an oil- and slip-resistant rubber sole, and side zipper, so you won’t have to deal with doing and undoing laces when taking them on and off. Motorcycle not required, but encouraged. 
 
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10

Best Tall Platform Boots

Truffle Collection platform knee high boot in snake.

Truffle Collection 

These very-’70s platform boots beg to be worn on the dance floor. They’re done in a rich-looking faux snakeskin truffle brown, with a squared-off toe and a flared covered block heel. For dressing up, they’re best worn with a skirt that hits above the knee, but if you want to wear them on a blustery day, add wool socks underneath and throw on a pair of ankle-cropped wide-leg jeans with an unfinished hem. So glam. 

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11

Best Tall Boots with a Low Heel

Vagabond Shoemakers Nicole Knee-High Boot.

Vagabond Shoemakers Nicole Knee-High Boot

Vagabond is a Swedish brand, known for producing well-made shoes with a fashionable ’90s grunge style. These tall boots are made of saddle leather, with a rounded square toe and 2-inch block heel. They come in butterscotch brown or black, and would look fab with a flared, wide wale corduroy midi skirt.

 
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12

Best Mid-Calf Tall Boots

Tamara Mellon Zag Boots.

Tamara Mellon Zag Suede Boot

We swoon over Tamara Mellon’s gorgeously designed shoes (and handbags!)—and that’s exactly the case with this mid-calf boot. With to-die-for perforated suede detailing and a killer stiletto heel, it’s hard to ask for more. Now, if we could only decide between the black and cognac. 

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13

Best Amazon Tall Boots

These tall boots are trend-forward, but will never go out of style. They have classic lines, and the snap detailing along the side prevents them from being too boring. They’re 100 percent leather, with a low, sturdy stacked heel, and they come in black- and dark-brown leather, and light-brown suede. These babies will turn heads. 
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14

Best Nordstrom Tall Boots

These stylish tall boots from Jeffery Campbell have an upscale look, with sleek lines, a glossy finish, and a 3-inch inverted triangle heel. They’re a great pick for anyone—the tan lizard print is just as fetching as the ivory crocodile print—but we especially like them for petite women, as the shaft is on the shorter side. They’re also lined with suede for extra warmth. Gorgeous. 

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