Casual Winter Looks

Casual winter looks make it easy to enjoy every chilly day, whether you’re heading out for a walk, gathering with friends, or simply relaxing at home. With comfortable layers and timeless styles, you can stay warm and look great all season long. Explore versatile options designed for lasting value—perfect for everything winter brings your way.

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476 Items

Women's Classic Lambswool Duffel Coat, Pattern

A classic duffel coat in royal red plaid, crafted from supersoft Italian lambswool with Thinsulate™ insulation.

Pros: Attractive appearance Stylish design Excellent warmth
Men's Scotch Plaid Flannel Shirt, Traditional Fit
Price was from: $59.95 now: $49.99

A soft, traditional fit flannel shirt in blue Mackellar plaid, made from high-quality Portuguese cotton.

Pros: Perfect fit Well-made Warmth Versatile Soft and comfortable material
Women's Quilted Quarter-Zip Pullover

A brown quilted quarter-zip pullover made from a soft cotton-polyester blend with a cozy brushed interior.

Pros: High quality and well made True to size with excellent fit Versatile style suitable for various occasions Warmth and great for layering Exceptionally comfortable and cozy
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
Price was from: $59.95 now: $49.99

A slightly fitted flannel shirt in authentic Scottish tartan, made from high-quality Portuguese cotton.

Pros: Great fit High quality Softness Warmth Comfortable
Women's Ultrawarm Coat, Three Quarter Length

A three-quarter length down coat with water-repellent insulation and removable faux fur hood, in graphite heather.

Pros: Fit Lightweight Length Color Warmth
Men's L.L.Bean Sweater Fleece Full-Zip Jacket

A grey heather full-zip jacket with a rugged exterior and soft interior, made from 100% polyester fleece.

Pros: Warmth Soft fleece interior Quality workmanship Durability Good fit
Women's Cotton Ragg Sweater, Funnelneck Pullover
Price was from: $79.95 now: $63.99

A lightweight tan funnelneck pullover crafted from midweight cotton yarns with classic ragg styling.

Pros: Warm and cozy Versatile and attractive color Comfortable fit Soft cotton material Flattering style
Women's Ultrawarm Coat, Long

A long, hooded winter coat with 650-fill DownTek™ insulation, water-resistant polyester/nylon shell, and faux fur trim.

Pros: Exceptional warmth Lightweight design High-quality construction Stylish appearance Comfortable fit
Women's Cotton/Cashmere Sweater, Crewneck

A luxurious sea salt crewneck sweater made from 95% cotton and 5% cashmere for lightweight warmth.

Pros: Great fit High quality Exceptional comfort Casual style Soft texture
Men's 3-Season Bomber Jacket

A hazelnut, wind-and water-resistant jacket with a recycled nylon shell and soft fleece lining for warmth.

Pros: Great fit Warm and dry Stylish design Easy to wash Nice color
Women's Ultrawarm Jacket

A stylish, water-resistant winter jacket with 650-fill-power down, removable hood, and multiple pockets.

Pros: Lightweight Stylish design Warmth Comfortable Good fit
Men's Waterfowl Sweater Vest

A naturally water-repellent merino wool vest with leather accents, fleece-lined pockets, and a microsuede collar.

Pros: Fit Quality Warmth Comfortable Versatility
Men's Mountain Classic Puffer Jacket

A blue, slightly fitted puffer jacket with ColdShield™ insulation, offering lightweight warmth and weather protection.

Pros: Stylish and versatile Comfortable and true to size Good value for money Lightweight and warm High quality and durable
Men's Mountain Classic Down Parka

A nautical navy parka with 650-fill DownTek™ insulation, water-resistant shell, and adjustable insulated hood.

Pros: High quality Lightweight Warmth Functional hood Comfortable fit
Men's Double L® Chinos, Natural Fit, Plain Front, Flannel-Lined

A pair of dark khaki cotton chinos, flannel-lined for warmth, perfect for chilly weather.

Pros: Keeping knees warm Quality workmanship Warmth Good fit Comfortable
Women's Rugged Ridge Parka

A waterproof, wind-resistant winter parka with PrimaLoft insulation and a microfleece-lined collar for extra comfort.

Pros: Waterproof Warmth Durable Comfortable fit Roomy pockets
Women's Classic Lambswool Peacoat

A light gray heather lambswool peacoat with Thinsulate™ insulation, smooth polyester lining, and nautical buttons.

Pros: Fabric quality Warmth Classic style Beautiful color Versatility
Men's Mountain Classic Windproof Fleece Jacket
Price was from: $120 now: $95.99

A gray windproof fleece jacket with AirShield® technology, offering exceptional breathability and softness.

Pros: Windproof High quality Versatile Good color Comfortable fit
Men's Insulated 3-Season Bomber Hooded Jacket

A windproof, water-resistant bomber jacket with recycled polyester insulation and cozy fleece lining in thyme.

Pros: Good quality Warmth Versatile Comfortable Looks great
Women's Classic Lambswool Polo Coat, Three-Quarter Length

A timeless light gray heather coat made from 100% Italian lambswool with Thinsulate™ insulation.

Pros: Beautiful design High-quality wool material Perfect fit Classic style Excellent warmth
Women's Ultralight 850 Down Sweater

An ultralight, water-repellent black down sweater with recycled nylon shell, perfect for layering and travel.

Pros: Lightweight Well-made Good for layering Warm Comfortable
Women's Classic Lambswool Duffel Coat

A luxurious Italian lambswool duffel coat in camel with Thinsulate™ insulation and an attached hood.

Pros: Durable and well-made Stylish with cheerful colors Soft and warm lambswool Comfortable fit Attached hood
Women's Cotton Ragg Sweater, Open Cardigan Fair Isle
Price was from: $99 now: $74.99

An open-front cardigan in brown cotton yarns, featuring a classic Fair Isle pattern and ribbed trim.

Pros: High quality and durable construction Beautiful color and pattern Versatile and stylish design Comfortable and great fit Warm and cozy
Women's Maine Mountain Parka

A waterproof, windproof parka with 650-fill DownTek™ insulation and removable faux-fur hood, perfect for winter.

Pros: Flattering fit Quality construction Warmth Comfortable Versatility

Casual Winter Looks

When winter settles in and the days grow shorter, there’s a certain kind of comfort in reaching for your favorite layers—the ones that make cold mornings feel a little warmer and evenings by the fire even cozier. Casual winter looks are all about finding that perfect balance between warmth, comfort, and timeless style. Whether you’re heading out for a brisk walk with the dog, meeting friends for coffee, or simply enjoying a quiet afternoon at home, the right pieces make all the difference. Think soft, heavyweight flannels that feel like a gentle hug, versatile sweaters that go from the office to the weekend without missing a beat, and durable outerwear designed to keep the chill at bay no matter what the forecast says. The beauty of these winter staples is their ability to adapt—layer them up for extra protection on the coldest days, or shed a piece or two when the sun peeks out. With thoughtful details like easy-to-use zippers, roomy pockets, and adjustable hoods, these clothes are made for real life, where practicality and comfort always come first.

For many, casual winter wear isn’t just about personal comfort—it’s about sharing warmth and thoughtfulness with others, too. These pieces make excellent gifts for anyone who loves spending time outdoors, whether they’re shoveling the driveway, playing in the snow with the kids, or simply enjoying the peaceful stillness of a winter morning. When you give someone a cozy pullover or a sturdy pair of boots, you’re not just giving them something to wear; you’re giving them the confidence to step outside and make the most of the season. And because these styles are built to last, they become part of winter traditions year after year—passed down, borrowed, and worn with fond memories. Families gather for sledding adventures, friends meet for snowy hikes, and neighbors catch up over steaming mugs of cocoa, all bundled up in layers that feel just right. For men looking to refresh their closets with reliable, comfortable options, our Casual Winter Wear for Men collection has everything needed to stay warm and look great, no matter what winter brings.

Choosing the right casual winter looks often comes down to the little things—the way a fleece-lined collar feels against your skin, the ease of slipping on a pair of pull-on boots when you’re rushing out the door, or the reassurance that your favorite jacket will stand up to years of snowy days and muddy thaws. It’s about versatility, too: pieces that work just as well for a spontaneous snowball fight as they do for a quick run to the store. The best winter wardrobes are built on layers that can be mixed and matched, adapting to changing weather and busy schedules alike. And while style is always important, it’s the comfort, durability, and lasting value that truly set these clothes apart. When you invest in quality winter wear, you’re choosing more than just a look—you’re choosing a season full of warmth, adventure, and connection, wrapped up in pieces you’ll reach for again and again.

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Casual Winter Looks