Cool Weather Boots

When the temperatures drop and the air turns crisp, it's time to step into a pair of cool weather boots that blend style with functionality. Whether you're exploring a frosty trail or strolling through city streets, our collection offers the perfect blend of durability and comfort to keep your feet warm and dry. Embrace the outdoors with confidence, knowing these boots are crafted to handle whatever the season throws your way. With timeless designs and versatile options, you'll find just what you need to enjoy every chilly adventure in comfort and style.

Sort by:

Filter & Sort

476 Items

Men's Storm Chaser 5 Slip-Ons

A tough, waterproof slip-on with leather upper, rubber outsole, and exceptional cushioning for all-weather comfort.

Pros: High quality Warm and cozy Versatile design Easy to slip on Comfortable fit
Men's Storm Chaser Boots 5, Zip

A gray all-weather boot with waterproof leather, PrimaLoft® insulation, and easy on/off side zip.

Pros: Comfortable for long hours of use Great fit and support Warmth and effective in cold weather High quality materials and construction Easy to put on and take off
Men's Stonington Boots, Moc-Toe

A rugged dark oakwood leather boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.

Pros: Durable construction Versatile use Lightweight design Stylish appearance Comfortable fit
Women's Bean Boots, 10" Shearling-Lined

A Maine-made boot with shearling lining, Thinsulate™ insulation, and waterproof leather/rubber for cold, wet conditions.

Pros: Comfy Good customer service High-quality shearling Durable Warm
Men's Storm Chaser Boots 5, Leather Lace-Up

A durable, all-weather black boot with waterproof leather, PrimaLoft® insulation, and a moisture-wicking synthetic mesh lining.

Pros: Perfect fit Comfort Warmth Great color Improved traction
Women's Snow Sneaker 5 Boots, Pull-On

A pull-on winter boot with ColdShield insulation, suede upper, and VertiGrip outsole for reliable traction.

Pros: Easy to pull on Comfort Warmth Good grip Well made
Women's Rugged Wellie® Chelsea Boots

A pair of black rubber Chelsea boots with EVA cushioning and VertiGrip outsole for wet conditions.

Pros: Fit Waterproof Quality Comfort Style
Women's Stonington Boots, Moc Toe
Price was from: $170 now: $135.99

A rugged dark oakwood leather boot with sneaker-like comfort, waterproof protection, and durable rubber outsole.

Pros: Great fit Versatile Comfortable Well made Looks great
Men's Bean Boots, 6.5" Chelsea

A waterproof Chelsea boot with buttery-soft leather and durable rubber, perfect for wet conditions.
Men's Bucksport Boots, Plain-Toe
Price was from: $220 now: $179

A rugged coffee bean leather boot with waterproof membrane, Vibram® outsoles, and anti-odor sock liner.

Pros: High quality Good traction Warmth Comfortable Water resistance
Men's Bucksport Boots, Cap Toe
Price was from: $200 now: $169.99

A rugged coffee bean leather boot with Vibram® rubber outsoles and waterproof oiled-leather upper.

Pros: Quality construction Waterproof Great color High comfort Useful side pockets
Men's Kangaroo Upland Hunter's Boots, Insulated

An 8" brown leather hunting boot with 200-gram Primaloft insulation and Vibram Mega-Grip outsole.

Pros: No break-in period needed High-quality leather Great traction Comfortable fit Excellent warmth
Men's Oboz Bridger Mid B-Dry Hiking Boots

A sleek, waterproof hiking boot with a leather upper, rubber sole, and superior arch support.

Pros: Light Sturdy Comfortable Good quality orthotic base Looks great
Men's Arctic Sport Muck Boots, Mid-Cut

A pair of black, mid-cut waterproof muck boots with insulated neoprene and rubber construction for extreme conditions.

Pros: High durability Lightweight All-around use Watertightness Keeps feet warm
Men's Lacrosse Insulated 1000G Alphaburly Pro Boots, 18"

A superwarm, waterproof hunting boot with 1000G Thinsulate insulation and excellent traction in mossy oak camouflage.

Pros: Ideal for cold weather Superb traction Perfect for wet environments Great in muddy conditions Excellent warmth
Men's Storm Chaser 5 Chelsea Boots

A rugged, waterproof Chelsea boot with PrimaLoft insulation, moisture-wicking mesh, and a siped rubber outsole.
Women's Storm Chaser 6 Lace-Up Boots, Waterproof Insulated

A waterproof, insulated boot with a faux fur collar, offering warmth and comfort in wet, cold conditions.
Men's Hybrid Wellie® Boots
Price was from: $119 now: $89.99

A rugged, waterproof boot with nubuck leather, neoprene upper, and VertiGrip rubber outsole for multi-surface traction.
Women's Maine Warden's Field Boot

A rugged, deepest brown leather boot with GORE-TEX, Primaloft insulation, and Vibram outsole for superior traction.
Men's Cresta II Waterproof Hiking Boots, Leather

A rugged brown leather hiking boot with waterproof protection, Vibram® sole, and cushioned EVA footbed.
Men's BOA® Technical Upland Boot

A lightweight, waterproof upland boot with a BOA lace system, goat leather upper, and Vibram® outsole.
Men's Stonington Chelsea Boots, Suede
Price was from: $150 now: $124

A rugged, deepest brown suede pull-on boot with sneaker-like comfort and shock-absorbing foam insole.
Women's Stonington Chelsea Boots, Suede
Price was from: $150 now: $119.99

A rugged, graphite suede Chelsea boot with sneaker-like comfort, moisture-wicking lining, and durable rubber outsole.
Women's Trailduster Hiking Boots
Price was from: $149 now: $109

A pair of waterproof nubuck leather hiking boots with EVA midsole and VertiGrip rubber outsole for all-day comfort.

Cool Weather Boots

As late summer breezes give way to crisp mornings and the leaves begin their annual transformation, it’s time to start thinking about cool weather boots—those reliable companions that make every outdoor moment more comfortable, no matter what the forecast brings. Whether you’re headed out for a weekend hike through golden forests, cheering on the sidelines at a chilly soccer game, or simply taking the dog for an early morning walk, the right pair of boots can make all the difference. Cool weather boots are designed to handle the unpredictable mix of conditions that autumn and early winter can bring—from sudden rain showers to frosty ground. Quality boots offer more than just warmth; they provide dependable traction, lasting durability, and a level of comfort that encourages you to linger outside a little longer, even when the air turns brisk. Many families keep a pair or two by the door, ready for everything from raking leaves to impromptu backyard gatherings around the fire pit. For those who love to travel, packable, versatile boots are a must for fall foliage road trips and cabin getaways.

These boots also make thoughtful gifts, especially for students heading off to college, new homeowners, or anyone who enjoys spending time outdoors regardless of the temperature. Choosing the right pair involves considering a few key details: insulation for warmth, rugged outsoles for grip on slippery paths, and easy on/off features for those quick dashes outside. Some folks prefer boots that pair easily with jeans and flannels for a timeless, laid-back style, while others look for options with extra cushioning for long walks. If you’re shopping for someone else, think about their daily routine—do they need a pair for commuting, for tackling yardwork, or for cozying up by the campfire? With so many styles available, it’s easy to find boots that fit seamlessly into any lifestyle, offering the kind of dependable comfort that turns even the simplest outing into something memorable.

As the season progresses and the air grows colder, many turn to boots with softer linings and flexible materials for ultimate comfort—perfect for those who want to keep their toes warm without sacrificing ease of movement. If you’re looking for something especially cozy for yourself or as a gift, you’ll find plenty of inspiration in our selection of Soft Winter Boots. These options are ideal for everything from après-ski evenings to quick trips to the mailbox on frosty mornings. No matter how you spend your time outdoors, a reliable pair of cool weather boots is a smart investment in comfort, durability, and lasting value—ensuring you’re always ready for whatever the season brings.

It's time to upgrade your browser

Cool Weather Boots