The 9 best winter boot styles for women, from comfortable block-heels to trendy Western styles

OSTN Staff

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Collage of the best winter boots for women, including Dr Martens, Daisy, and Charles & Keith 4x3
  • This winter’s best boot styles offer sleek and practical silhouettes.
  • Bolder trends of the season include knee-high boots, extra-chunky lug soles, and Western boots.
  • Explore the best boot trends of the year and shop styles in a range of price points.

The calendar year can loosely be broken up into two categories: open-toe-shoe season and boot season. And though we’re squarely in the latter, there is still much time left to enjoy a sleek, sturdy combat silhouette or classic bootie that suits a work or weekend wardrobe. But seeing as the market for boots – all heights, styles, and finishes – can seem like a bottomless pit, we’ve edited down the options to the nine most essential trends to know.

With a blend of timeless silhouettes and styles that have been inspired by runways around the world, the best boots of 2021 may largely appeal to those who prioritize comfort and practicality. This can be found in designs with chunky lug soles, sturdy block heels, and shafts with an elastic band that slip on easily and keep a snug fit to the ankle. For all else, a statement-making knee-high option in embossed croc or a festive Western boot offers a slightly more trend-forward – daring, even – approach to the season’s most in-demand footwear.

Ahead, a complete breakdown of the best boots for winter for all budgets and tastes.

Here are the best winter boots for women in 2021:

Table of Contents: Masthead Sticky

Chelsea Boots

Thursday Boots Duchess worn on rain-soaked pavement with orange leaves

The iconic Chelsea boot is a timeless fall and winter essential, namely in the standard low heel, rounded toe, elastic-paneled style. This boot lends itself to casual outfits — jeans and a T-shirt are all you need — but it’s also a sturdy, non-fussy boot that compliments a moody floral dress or slinky silk skirt, too.

Our top picks for Chelsea boots:

The Duchess (small)Chain-Trim Heel Chelsea Boots (small)The Italian Leather Square Toe Chelsea Boot (small)The Noemi Boot (small)Melissa Chelsea Boots (small)
Western Boots

Tecovas The Daisy worn by woman wearing cropped jeans sitting and playing a guitar

Western boots are instantly recognized for their stacked heel, embroidered design, and often, though not always, taller shaft. Though it can bring to mind cowboys and rodeos, this style of boot is also super versatile. It adds a bit of nostalgia and rustic glamour to any ensemble, without ever feeling costumey.

Our top picks for Western boots:

Heritage D Toe StretchFit Western Boot (small)Shyanne Blanca Western Boots (small)Vegan Daley Ankle Boots (small)Ackella Bootie (small)The Daisy (small)
Combat Boots

Dear Frances Park Boot in espresso worn by woman seated on a wooden chair wearing tan knee-length shorts, white top, and beige cardigan

Though the combat boot may inherently be associated with uniform wear, the fashion industry has embraced it in a way that makes the sleek silhouette and tough lace-up exterior a go-to choice for all style points of view. This season, options range from minimal leather boots that can be casual or dressed up to chunkier soles that’ll prove helpful during more challenging weather conditions.

Our top picks for western boots:

Evan Lace Up Combat Boots (small)Donita Combat Boot (small)1460 Smooth Leather Lace Up Boots (small)Jordan Boot (small)Park Boot (small)
Ankle Boots

Pêche Ren boots in blue, yellow, white, and black arranged in a circle on a gray floor

Classic ankle boots are unrivaled. The silhouette is easy to wear and provides the perfect shaft height for tossing on with jeans, trousers, dresses, and skirts of varying lengths. The choice ankle boots for 2021 have a clean aesthetic, with a buttery leather (real or vegan) texture and mid-height heel in a not-too-thin, not-too-clunky weight. For anyone who prefers a shoe that’s refined yet minimal, this is the one you’ll reach for day after day.

Our top picks for ankle boots:

Point Boot (small)Ren (small)Heel Leather Ankle Boot (small)Wally Leather Ankle Boots (small)Tarah Leather Bootie (small)
Tall Boots

Woman wearing long brown skirt with high slit and black zara heeled knee-high boots

Boots that graze the knee, or even extend slightly above it, tend to draw some attention. It’s a confident style choice and one that will be ubiquitous this winter. The most popular tall boots of the season come in earthy neutral tones, rich croc textures, and skin-tight fits that blur the lines between leggings and footwear.

Our top picks for tall boots:

Ronstadt Boot (small)Sulema Knee High Boot (small)Randall Goldy Knee High Boot (small)Heeled Knee-High Boots (small)Women’s Hiya Heeled Boots (small)
Lug Sole Boots

Rag & Bone Shiloh Sport Zip Boot in brown worn with cuffed slim jeans

At the midpoint of bold style and true utilitarianism are this season’s amped-up lug sole boots. The silhouette is similar to a Chelsea or combat boot, but the differentiating detail is the extra thick sole that provides a boost of additional height (without balancing on a spindly heel) and a substantial silhouette that makes any ensemble a bit more grounded and less delicate. 

Our top picks for lug sole boots:

Pull On Combat Boots (small)Celina Lug Chunky Sole Boots (small)Leather Mid Chelsea Boots (small)Allout (small)Shiloh Sport Zip Boot (small)
Block Heel Boots

Nomasei Aria Stretch Nappa White Pompeii Boots worn on pavement

As mentioned before, the best boots for winter include a variety of comfortable styles, like booties with heels that are made for those who spend long hours on their feet. Available in a wide stretch of price points, the block heel is the alternative to a spiky stiletto heel, and whose shape looks, for lack of a better term, like a block. The tops of the boots remain simplistic and elongated, while the bottoms provide generous support. 

Our top picks for block heel boots:

Cube Heel Ankle Boots (small)Davinna Bootie (small)Jarli High Heel Booties (small)The Boot (small)Aria Stretch Nappa White Pompeii Boots (small)
Flat Boots

Gray Matters Mara Boots Cacao worn by woman walking and wearing a black top, blue knee-length shorts, and sheer tights

Heels and heavy soles aside, one of the most popular boots styles of the moment is flat. With a taller shaft, this silhouette often hits mid-calf or at the knee. Some resemble a classic riding boot, while others are even more pared-back for a chic minimalist aesthetic. The result is a bold silhouette choice that’s wearable for every day.

Our top picks for flat boots:

Nella Leather Boot (small)Fable Tall Boot (small)Mara Boots Cacao (small)Knee-High Leather Riding Boots (small)Rilee Leather Boot (small)
Sculptural Heel Boots

Woman wearing Charles and Keith Sculptural Heel Ankle Boots in black with knee-length white A-line dress

Rounding off the best boots for winter is a style with a unique twist, quite literally, at the heel. Sculptural-heeled boots have a clean silhouette that offers a bit of unexpected drama with heels in more unconventional shapes and textures, including curved lives, stacked pebbles, and geodesic domes.

Our top picks for sculptural heel boots:

Marnie Boot Stretch Nappa Black (small)Daylee Boot (small)Sculptural Heel Ankle Boots (small)Jadran Sock Bootie (small)Devon Beatle 95mm Boots (small)

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