The products listed here were independently selected by a member of the editorial staff. Should you choose to purchase a product through a link on this page, we may receive an affiliate commission.

Image: Sway and Cake

A fresh, fun, and ultra comfortable pair of boots can make you feel (and walk) like a whole new woman. If you're looking to add a new pair to your closet—and, let's be honest, who isn't?—narrow down your options with this list of cold-weather picks.

Billini Xanti Lace-Up Boot, Sway and Cake Local


Image: Sway and Cake

Bring on the compliments: These ankle boots feature a chunky sole and a cool buckle detail that add on-trend detail to a classic silhouette. Pike/Pine

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Blundstone 500 Original, Market Street Shoes Local


Blundstone's lightweight and durable chelseas shape to the foot for optimal comfort. With a slip-resistant outsole and waterproof upper, they're the ideal boots to pair with jeans for casual everyday wear. Ballard

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Intentionally Blank Pammy Mid-Height Boot, Corre Local


Image: CORRE

This cold-weather variation on Intentionally Blank's popular Pam shoe is made in Spain with soft patent leather uppers for a look that's super chic. Madrona

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Officine Creative Mercy Boot, A Mano Local


Image: A Mano

Artisan-focused boutique A Mano carries this unique ankle boot with a sculpturesque block heel and a wine-colored, airbrushed finish that's as fun as it is luxurious. Downtown

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Clarks Women Desert Boot, Re-Soul Local


Image: Re-Soul

These Clarks may be desert boots, but their lightly worn leather uppers and classic shape scream PNW fashion. Embody the perfect level of "tried, but not too hard" by pairing them with some snazzy socks and your favorite denim. Ballard

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Lili Mill Olive Grey Heeled Bootie, Sole Food Local


Image: Sole Food

Sporting a striking olive color, a sleek block heel, and an asymmetrical cutout, this ankle bootie feels fierce and I'm-the-boss important—while ultra-soft leather makes it fun to break in. University Village

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Alohas West Boot, September Local


Looking for a pair of boots that looks as great with skirts as it does with jeans? Handmade and designed in Spain, this square-toe option rocks an elegant wooden heel, a slim silhouette, and a subtle color contrast that proves all those warnings against pairing black with brown dead wrong. Ballard

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Vagabond Blanca Boots, Pipe and Row Local


Image: Pipe & Row

Embossed leather snake print Vagabond boots are your quickest route to feeling like an '80s rock star—though a square toe and flare block heel keep the look thoroughly modern. Prefer a more neutral addition to your wardrobe? Opt for the equally fashionable lark. Fremont

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Reed Riding Boot, Nordstrom Local


Image: Nordstrom

It wouldn't be a fall boots list without a knee-high classic. Keep it cozy and still make an impression by pairing these buckle-adorned boots (available in brown or black) with a mini skirt and tights, or a sweater dress and leggings.

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Vegan Jadon II Platform Boots, Dr. Martens


Image: Dr. Martens

Docs are the kind of shoe that makes you feel empowered—and this vegan version in cherry red packs all the quality and craftsmanship of the classics, with none of the animal rights qualms. Stomp away.

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