Top 10 Casual Boots for Chilly Season

Top 10 Casual Boots for Chilly Season

With cooler temps comes many occasions—which means you’ll need boots that’ll last! Anchor your autumn-to-winter wardrobe with our best arrivals built for comfort, style, and a seamless seasonal transition.

Birkenstock Women’s Uppsala Mid Lace-Up - Suede

Velvety suede and a contoured cork footbed offer that cool, calm, and collected look.
Shop Uppsala Mid Lace-Up - Suede

VIONIC Women’s Uptown Sur Booties

Travel plans on the agenda? Take these functional and flexible favorites with you.
Shop Uptown Sur Booties

Sam Edelman Women’s Laguna Weatherproof Boot

The perfect Chelsea boot—designed for style statements and practicality.
Shop Laguna Weatherproof Boot

Columbia Women’s Moritza™ Shorty

No rain checks here! Waterproof boots are made to keep you going.
Shop Moritza™ Shorty

Koolaburra by UGG Women’s Koola Ultra Mini

A trendy choice with plush lining for nonstop cuteness and all-day warmth.
Shop Koola Ultra Mini

Kamik Women’s Tundra

Insulated coverage ensures you never miss out on cold-weather fun.
Shop Tundra

Frye Women’s Harness 12R

Meet your new favorite—a timeless, leather boot that gets better with age.
Shop Harness 12R

Naturalizer Women’s Deesha

Casual enough for all-day wearability, elegant enough for all the festivities.
Shop Deesha

Hunter Women’s Diana

Get outside without any worries! This cozy pick is sure to keep you snug and dry.
Shop Diana

Thorogood Men’s American Heritage Square Toe Wellington

A go-to boot that can handle pretty much anything all year long. What’s not to love?
Shop American Heritage Square Toe Wellington

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