10 Best Shoes for Fall and Winter

Navigating fall and winter weather demands footwear that can handle unpredictable conditions wet leaves, slick sidewalks, freezing temperatures, and even snow. Choosing the right shoes during these seasons isn’t just about style it’s about staying safe, warm, and comfortable. Shoes with strong grip, weatherproof materials, and solid insulation are essential to prevent slips, keep your feet dry, and avoid cold-related discomfort.

Fall and winter shoes should also offer comfort for all-day wear, whether you’re commuting, walking, or exploring outdoors. With so many options on the market, selecting the right pair can be overwhelming. This guide breaks down the must-have features, what to avoid, and answers common questions so you can confidently invest in shoes that will keep you steady and stylish through the chilliest months.

Best Shoes for Fall and Winter

1. Sorel Caribou Boot

The Sorel Caribou Boot is a winter legend, combining time-tested construction with modern comfort. Designed to thrive in snow, slush, and bitter cold, this boot features a waterproof nubuck leather upper paired with a seam-sealed design to keep moisture out. Inside, it houses a removable 9mm ThermoPlus felt inner boot, which adds insulation down to -40°F, making it a solid choice for deep-winter wear. The handcrafted waterproof vulcanized rubber shell and herringbone outsole offer reliable traction on ice and snow-covered surfaces.

Despite its rugged build, the Caribou Boot doesn’t compromise on comfort. The plush inner lining feels soft against the foot, while the EVA midsole ensures cushioning over long wear. Although it’s not the lightest boot on the market, its bulk is justified by the protection it offers. It also has a classic look that pairs well with winter outerwear.

This boot is especially well-suited for rural or suburban wearers dealing with heavy snow, though it may feel overbuilt for city slickers facing slush and rain. The generous toe box also allows room for thick socks without cramping. As a bonus, the felt liner can be removed to dry out faster, increasing the boot’s versatility and hygiene. Sorel has earned a reputation for making boots that last, and this model lives up to that standard.

Whether you’re shoveling snow, hiking in sub-zero temperatures, or commuting during a snowstorm, the Caribou Boot delivers unmatched warmth and waterproofing. It’s more than just a seasonal accessory it’s winter armor for your feet. While pricier than some alternatives, the long-term value and performance make it worth every penny.

Pros:

• Superior insulation rated to -40°F

• Waterproof nubuck leather and vulcanized rubber shell

• Excellent grip with herringbone outsole

• Durable, long-lasting build

• Removable liner for easy drying

Cons:

• Heavy and bulky for casual use

• May be too warm for mild climates

• Not ideal for indoor wear due to size

2. Merrell Thermo Chill Mid Waterproof

The Merrell Thermo Chill Mid Waterproof boot blends hiking performance with winter readiness. It’s a go-to for anyone who needs lightweight winter protection for trails or everyday errands. The upper combines waterproof PU-coated leather and mesh, ensuring durability and breathability while resisting moisture from snow or rain. The M Select™ DRY technology keeps your feet dry by sealing out water and allowing sweat to escape.

Insulation is handled by 200g M Select™ WARM lightweight synthetic fill, which balances warmth without overheating. A fleece lining adds a soft touch, enhancing in-shoe comfort for extended wear. Unlike bulky snow boots, the Thermo Chill has a nimble silhouette and trail-ready outsole that grips well on slick and muddy terrain. The molded nylon arch shank and EVA midsole provide stability and cushioning underfoot.

This boot is ideal for light hiking, dog walking, and cold-weather commuting. It offers ankle support without restricting movement, making it a good fit for active lifestyles. The bellows tongue also keeps out debris, which is a major plus for trail use. Whether you’re tackling a wet park path or a frozen gravel lot, this boot keeps you moving with confidence.

Merrell’s outdoor heritage is clear in the thoughtful details and rugged performance of the Thermo Chill. It’s not built for the Arctic tundra, but for the majority of fall and winter conditions in temperate zones, it performs admirably. The balance of function, comfort, and value makes it one of the best midweight winter boots available.

Pros:

• Lightweight and agile feel

• Effective waterproof and breathable construction

• Solid ankle support for active use

• 200g insulation suitable for most winter days

• Excellent traction on varied terrain

Cons:

• Not suitable for deep snow or extreme cold

• Slightly narrow fit for wide feet

• Lacing system could be more secure

3. Blundstone Thermal 566 Chelsea Boot

The Blundstone Thermal 566 is a versatile Chelsea boot designed for cold-weather wear with a rugged twist. Made from premium waterproof leather and featuring elastic side panels, this boot offers convenience and style without sacrificing protection. Unlike standard Chelsea boots, the Thermal 566 is fully lined with Thinsulate™ insulation and features a sheepskin footbed, adding warmth and plush comfort during chilly months.

The outsole is made from a slip-resistant TPU material, providing dependable grip on wet sidewalks or icy stairs. The boot’s dual pull-tabs make it easy to slip on and off perfect for quick transitions from indoors to outdoors. Its understated design allows it to work well with jeans, chinos, or casual office attire, bridging the gap between utility and urban style.

This Blundstone model is great for those who want warmth without the look or feel of a traditional winter boot. It handles cold, wet conditions well, especially in urban settings, though it may not be ideal for heavy snow or backcountry trekking. The removable sheepskin footbed also adds a layer of insulation underfoot and can be replaced or washed when needed.

While it lacks the deep lugs of a snow boot, its traction is surprisingly reliable for everyday winter walking. The Thermal 566 is also a strong option for travelers looking for a compact, packable cold-weather shoe. Overall, it’s a premium choice for fall and winter versatility wrapped in a sleek silhouette.

Pros:

• Waterproof leather with Thinsulate™ lining

• Stylish and minimal design for daily wear

• Sheepskin footbed adds warmth and comfort

• Easy pull-on construction

• Excellent craftsmanship and durability

Cons:

• Limited traction in deep snow or icy trails

• No lace system for fit adjustment

• Premium price point

4. Columbia Bugaboot Celsius Plus Omni-Heat

The Columbia Bugaboot Celsius Plus Omni-Heat is built for serious winter adventurers. With 400g insulation and Omni-Heat reflective lining, it offers exceptional warmth for sub-zero outings. Its leather and textile upper is sealed for waterproofing, and a tall shaft design keeps snow and slush out even in deep winter terrain. The Techlite+ midsole provides responsive cushioning for active movement.

One of the standout features is Columbia’s proprietary Omni-Grip™ rubber outsole, which ensures strong traction over ice, snow, and wet ground. Despite its rugged construction, the boot remains comfortable thanks to a molded toe cap, cushioned collar, and adaptive fit. It’s the kind of boot you can wear from the cabin to the mountain with full confidence in its protection.

The Bugaboot Celsius Plus isn’t just about brute force insulation it’s also supportive for long treks. The midsole has a springy feel, keeping your step energized even in frozen conditions. At 400g insulation, it is warmer than most everyday winter boots, making it overkill for mild climates but perfect for true cold-weather regions.

Columbia has engineered this boot for durability, performance, and function in one package. It’s bulky and not exactly fashion-forward, but it’s made for those who prioritize warmth and safety over sleek aesthetics. If you brave heavy snow or need dependable winter gear, this boot has you covered.

Pros:

• 400g insulation plus Omni-Heat reflective lining

• High-traction Omni-Grip™ outsole

• Waterproof construction with high shaft coverage

• Cushioned and supportive for long treks

• Ideal for harsh winter environments

Cons:

• Bulky and heavy

• Too warm for fall or mild climates

• Style may not suit urban wear

5. The North Face VECTIV Fastpack Insulated FUTURELIGHT

The VECTIV Fastpack Insulated FUTURELIGHT from The North Face is a modern solution for active winter wear. This shoe blends sneaker-like agility with the warmth and protection of a winter boot. FUTURELIGHT technology offers waterproof breathability, allowing vapor to escape while blocking out moisture. The 200g synthetic insulation ensures cold-weather readiness without weighing the shoe down.

What sets this shoe apart is the VECTIV midsole, which combines a rocker shape and stabilizing plate for energy return and foot stability. This is especially helpful when walking on slick sidewalks or uneven icy paths. The SurfaceCTRL™ rubber outsole is tuned for winter grip, offering traction you can trust even on packed snow.

It’s designed for those who want performance, warmth, and mobility all in one. Ideal for commuters, winter hikers, and travelers, the Fastpack works well across a range of winter conditions, from city streets to rural trails. Its ankle-height design provides good coverage without limiting motion, and the reinforced toe cap enhances protection from rocks or ice.

If you need something lighter than a boot but tougher than a sneaker, this hybrid hits the sweet spot. The North Face has managed to create a truly all-terrain shoe for fall and winter without compromising on looks or performance. It’s athletic, reliable, and built for motion.

Pros:

• Lightweight and energetic feel with VECTIV midsole

• Waterproof and breathable FUTURELIGHT membrane

• 200g insulation for moderate winter protection

• Excellent grip with SurfaceCTRL™ outsole

• Hybrid design for versatile use

Cons:

• Less warmth than insulated boots for extreme cold

• Not suited for deep snow

• Pricey for a sneaker-like shoe

6. Timberland 6-Inch Premium Waterproof Boot

A staple for fall and winter wardrobes, the Timberland 6-Inch Premium Waterproof Boot offers a perfect balance of rugged durability and urban style. Its seam-sealed waterproof leather upper keeps moisture at bay during wet autumn days and snowy winter conditions. The boot’s padded collar ensures a comfortable ankle fit, while its classic lace-up design allows for a secure feel across all foot shapes.

Inside, it features PrimaLoft® insulation to keep your feet warm even when the temperatures dip. The cushioned EVA footbed and anti-fatigue midsole absorb shock and provide all-day comfort, ideal for work, commuting, or casual outings. The rubber lug outsole gives this boot strong traction on slick sidewalks, icy driveways, or leaf-covered streets.

Timberland’s premium build is as much about looks as performance. The wheat nubuck colorway is iconic, though other color options offer versatility for dressier or more rugged settings. It works equally well with jeans or workwear, making it a stylish yet practical choice for multi-season use. The leather ages beautifully, developing a unique patina over time.

This boot does require a short break-in period, but once it molds to your feet, it becomes a go-to for cold-weather comfort. While not the lightest on this list, the Premium 6-Inch Boot is tough, timeless, and ready to take on fall and winter.

Pros:

• Waterproof leather construction

• 200g PrimaLoft® insulation for warmth

• Iconic styling and versatile wear

• Durable lug outsole for great traction

• Comfortable cushioned midsole and collar

Cons:

• Slightly heavy for prolonged walking

• Requires break-in period

• Not ideal for deep snow coverage

7. KEEN Revel IV Polar Boot

The KEEN Revel IV Polar Boot is purpose-built for winter adventures with a focus on warmth, comfort, and traction. Designed for freezing conditions, it features 200g KEEN.WARM insulation and a heat-trapping thermal insole. The waterproof leather and mesh upper is reinforced with KEEN.DRY membrane to keep moisture out and allow heat to circulate.

This boot truly excels in extreme conditions with its KEEN.POLAR TRACTION outsole, designed to bite into ice and snow. The stability shank and mid-cut profile support your ankle, making it ideal for hiking, trekking, or long winter walks. Unlike many winter boots, it remains flexible and doesn’t feel overly stiff during movement.

Inside, the plush lining and cushioned footbed create a cozy environment, even on long days outside. The boot also uses eco anti-odor technology, which helps keep it fresh even after repeated wear in damp conditions. KEEN’s toe bumper offers added protection, especially for those using the boot in outdoor or work settings.

This is not your average winter boot it’s for those who brave real cold and unpredictable terrain. Whether you’re navigating icy trails or walking the dog in snow-packed neighborhoods, the Revel IV Polar delivers warmth, grip, and security.

Pros:

• KEEN.POLAR TRACTION for icy grip

• 200g insulation with heat-reflective insole

• Waterproof and breathable KEEN.DRY upper

• Supportive and protective construction

• Comfortable out of the box

Cons:

• Heavier than casual boots

• Less stylish for office or city use

• May run warm for fall conditions

8. UGG Butte Boot (Men) / UGG Adirondack III Boot (Women)

UGG’s cold-weather offerings go beyond slippers—the Butte Boot for men and Adirondack III for women are standout winter performers. Both feature waterproof leather and suede uppers with sealed seams to keep water and snow out. Their interiors are lined with genuine UGGpure™ wool, a naturally moisture-wicking material that provides luxurious warmth.

These boots are rated to -25°F, making them highly suitable for cold winters. They also include Vibram® outsoles, known for superior traction across slick, icy, and uneven ground. The cushioning insole provides day-long comfort, while the flexible shaft can be worn up for snow protection or folded down for a sheepskin-trimmed look.

Despite their premium appearance, these boots are rugged and highly functional. They handle snow, slush, and ice with ease while remaining stylish enough for city errands or travel. The lacing system offers solid lockdown, and the high shaft prevents snow intrusion.

UGG combines warmth, fashion, and function better than most brands in this category. Whether you’re winter hiking or shopping in snowy streets, these boots offer insulation and confidence without compromise.

Pros:

• Rated to -25°F with natural wool lining

• Vibram outsole for reliable grip

• Waterproof leather and seam-sealed build

• Flexible and stylish shaft design

• Plush, luxurious interior feel

Cons:

• Premium price

• Not ideal for wet fall weather without snow

• Slightly narrow toe box for wide feet

9. Salomon X Ultra Pioneer MID Climasalomon Waterproof

The Salomon X Ultra Pioneer MID blends trail-running DNA with winter functionality. Designed as a waterproof mid-cut hiking shoe, it’s perfect for fall and early winter thanks to its agile frame, solid grip, and weather-ready features. The Climasalomon™ waterproof membrane keeps feet dry through wet, muddy conditions, while the synthetic upper dries quickly after exposure to rain or snow.

While it lacks insulation for deep winter, it’s an excellent transitional option for those in milder climates or active users who generate their own warmth during hikes. The ADV-C chassis adds stability, especially on uneven terrain, and the Contagrip® outsole ensures secure traction in slippery conditions.

The mid-height design supports the ankle without restricting movement, and the molded OrthoLite® insole enhances comfort. With trail-performance features in a sleeker silhouette, it’s ideal for fall hikes, rainy days, and light snow.

It’s a top choice for outdoor enthusiasts or commuters who want a lightweight yet weather-capable shoe. As a bonus, it pairs well with performance apparel and isn’t overly bulky. While not made for frigid weather, it’s a great crossover shoe between seasons.

Pros:

• Lightweight, trail-friendly build

• Waterproof Climasalomon™ membrane

• Contagrip outsole for reliable traction

• Mid-cut stability and comfort

• Quick-drying and breathable materials

Cons:

• No insulation for extreme cold

• Limited snow protection

• Lacks fashion-forward appeal for city use

10. Bogs Classic High Insulated Boot

The Bogs Classic High Insulated Boot is a no-nonsense, all-weather performer made for wet, muddy, and snowy environments. Made from durable hand-lasted rubber over a 7mm Neo-Tech waterproof insulation, this boot is fully waterproof and comfort-rated to -40°F. It’s ideal for those needing full protection in wet fall weather or harsh winter storms.

Slip-on construction with side handles makes it easy to put on and take off, even with gloves. The interior is lined with Bogs Max-Wick™ to evaporate sweat and prevent moisture buildup, while the non-slip outsole delivers steady footing on slippery surfaces. The footbed is contoured and cushioned for comfort over long wear.

Unlike traditional winter boots with laces or buckles, the Classic High prioritizes function over form. It’s perfect for snow shoveling, yard work, or icy commutes. The flexible neoprene upper conforms to your calf and traps warmth effectively.

Though bulkier than others on this list, the performance in wet and snowy conditions justifies its size. Bogs delivers a reliable, waterproof option that handles everything from rain-soaked fields to snowy driveways.

Pros:

• Fully waterproof with -40°F rating

• 7mm Neo-Tech insulation for warmth

• Max-Wick lining keeps feet dry

• Slip-on with handles for convenience

• Great traction in mud and snow

Cons:

• Bulky silhouette

• Less breathable for mild fall days

• Not fashion-oriented for city wear

Buyer’s Guide

When shopping for fall and winter footwear, it’s important to prioritize function without sacrificing comfort or style. Here are the most important factors to consider:

1. Weather-Resistant Materials
Look for shoes made with waterproof or water-resistant materials such as Gore-Tex, treated leather, or rubberized uppers. These keep your feet dry in rainy fall conditions and slushy winter streets. Avoid canvas or mesh fabrics during this season, as they absorb water quickly and offer little protection against cold.

2. Insulation and Warmth
Shoes lined with fleece, wool, or Thinsulate provide critical warmth in winter. Breathable insulation helps regulate foot temperature and keeps moisture (like sweat) from building up inside. In fall, you might not need full insulation, but a light lining or thicker insole can help.

3. Grip and Traction
Outsoles with deep lugs and non-slip rubber (such as Vibram or Michelin soles) offer excellent grip on wet leaves, icy sidewalks, and snowy paths. Avoid flat soles or smooth outsoles, which can cause dangerous slips. Traction-enhancing features like winter-ready tread or ice-gripping rubber compounds make a huge difference.

4. Comfort and Fit
Cold weather often requires thicker socks, so look for shoes with enough room to accommodate that without becoming too tight. A supportive footbed with cushioning ensures comfort over long walks or extended wear. Also, ensure proper ankle support, especially in boot-style footwear.

5. Height and Coverage
Ankle-high or mid-calf boots are ideal for added warmth and coverage against snow or slush. Shoes with higher collars can also help prevent cold wind from creeping in. For city dwellers, low-cut waterproof sneakers with a sealed tongue may suffice during milder fall weather.

6. Durability
Rough weather can wear down materials fast. Opt for shoes with reinforced stitching, durable outsoles, and long-lasting uppers. Quality materials may cost more upfront but will last through multiple seasons.

7. Style Versatility
Many modern winter shoes balance performance with urban styling. Look for neutral colors, clean silhouettes, and options that can transition from outdoor settings to office environments or casual outings.

Avoid This: Thin soles, breathable mesh uppers, or shoes with poor tread patterns. These are often too cold, too slippery, or too permeable for fall and winter use.

FAQ

What features make a shoe ideal for fall and winter?
A good fall and winter shoe includes waterproof or water-resistant materials, insulated linings for warmth, and outsoles with excellent grip. These features help protect against wet, cold, and slippery conditions while ensuring all-day comfort and safety.

Can I wear regular sneakers in fall and winter?
You can wear sneakers in mild fall weather, but standard sneakers aren’t ideal for winter. They often lack insulation and grip. However, some brands now make winterized sneakers with weatherproof uppers and improved traction, which are better suited for colder months.

Are boots always better than shoes for winter?
Not necessarily. Boots offer more coverage and warmth, especially in snowy conditions, making them a great winter option. However, waterproof low-cut shoes with proper insulation and good grip can also perform well, particularly in urban environments with cleared sidewalks.

How do I maintain my shoes during the winter?
Clean them regularly to remove salt, dirt, and moisture. Apply waterproofing sprays or waxes to leather or fabric uppers to maintain water resistance. Let shoes dry completely after each use—avoid placing them near direct heat, which can damage materials.

Should I size up for winter shoes to fit thicker socks?
If you regularly wear thick wool socks, consider sizing up half a size to ensure a comfortable fit. However, shoes that are too large can cause blisters or instability, so always try them on with your winter socks before purchasing.

Is insulation necessary for fall shoes?
Not always. In early fall or mild climates, you might not need heavy insulation. Focus instead on shoes with solid outsoles and water-resistant uppers. But if your area gets colder quickly or you spend long hours outside, light insulation is beneficial.

What type of outsole is best for icy surfaces?
Outsoles with deep, multidirectional lugs and rubber compounds designed for cold weather provide the best grip. Some winter shoes even use specialized technologies like Arctic Grip or ice-grip rubber that maintain traction on slick, frozen surfaces.

Conclusion

Choosing the right shoes for fall and winter is crucial for staying safe, dry, and comfortable. The best footwear for these seasons combines insulation, waterproofing, reliable traction, and durable construction. Whether you need boots for deep snow or sneakers for wet city streets, investing in season-appropriate shoes ensures better performance, fewer slips, and healthier, happier feet all season long.