Mens Casual Winter Shirts

Mens casual winter shirts are designed to help you stay comfortable and confident when the temperatures drop. With timeless styles and versatile options, these shirts make it easy to layer up for everything from backyard gatherings to weekend errands. Enjoy lasting quality and dependable comfort, all in one collection—so you can focus on making the most of every winter day.

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504 Items

Men's Maine Guide Shirt with PrimaLoft

A warm PrimaLoft wool blend shirt in green and black check, ideal for layering and outdoor activities.

Pros: Great fit Excellent quality Warm and comfortable Durable material Stylish appearance
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A charcoal heather flannel shirt with sheepskin shearling lining, offering softness, warmth, and wrinkle resistance.

Pros: Great fit High quality Softness Warmth Comfortable
Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley

A traditional fit Henley with a wool blend outer layer and soft cotton inner, in black cherry heather.

Pros: Good quality Warmth True to size Comfortable fit Versatility
Men's Maine Guide Sherpa Lined Wool Shirt

A men's wool blend shirt in red and black, lined with recycled polyester sherpa fleece for ultra warmth.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged midweight cotton flannel shirt in currant plaid, slightly fitted with a trimmer waist.

Pros: Great fit High-quality material Well-built Very comfortable Excellent return policy
Men's Fleece-Lined Flannel Shirt, Traditional Fit

A supersoft coal plaid shirt with 100% cotton flannel and cozy polyester fleece lining.

Pros: Quality Comfort Warmth Softness Versatility
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

A green chambray shirt with stretch, moisture-wicking cotton blend, perfect for untucked casual wear.

Pros: Great fit High quality Attractive color Versatile design Excellent comfort
Men's Maine Guide Shirt

A durable, 85% wool and 15% nylon plaid shirt, perfect for layering in red and black.

Pros: Great fit High quality Good quality Stylish Warm
Men's Signature Donegal Woven Shirt, Long-Sleeve
Price was from: $79 now: $54.99

A rugged light russet shirt with Donegal flecks, made from 100% cotton twill flannel.
Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit, Plaid

A lightweight brown corduroy shirt with a vintage plaid pattern, washed for extra softness and comfort.
Men's Chamois Shirt, Traditional Fit, Plaid
Price was from: $84.95 now: $69.99

A heavyweight chamois flannel shirt in barley plaid, offering exceptional softness and durability.

Pros: Great fit High durability Exceptional warmth Comfortable feel Excellent quality
Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted

A slightly fitted, ultrawarm plaid shirt with Sherpa fleece lining, made from 100% cotton flannel.

Pros: Soft and cozy Versatile design Great warmth High-quality construction Comfortable fit
Men's Comfort Stretch® Corduroy Shirt, Long-Sleeve, Traditional Untucked Fit
Price was from: $69.95 now: $49.99

A casual silver birch corduroy shirt with added stretch for comfort, perfect for untucked wear.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit

A rugged brown cotton flannel shirt with a soft brushed finish and durable triple-needle stitching.
Men's Sunwashed Canvas Shirt, Traditional Fit

A prewashed, 100% cotton canvas shirt in bay leaf, offering a relaxed fit with durable double-needle stitching.

Pros: Durable Comfortable Good fit Nice color Well made
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A wrinkle-free blue check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: High quality Wrinkle-free Lightweight Good fit Comfortable
Men's Scotch Plaid Flannel Shirt, Traditional Fit

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
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print

A green chambray shirt with stretch, moisture-wicking cotton blend, perfect for untucked casual wear.

Pros: High quality material Well made Good stretch Soft fabric Comfortable fit
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit

A slim-fit chamois flannel shirt in barley, made from 100% cotton and brushed for softness.

Pros: Perfect fit Great quality Softness Warmth Durability
Men's Maine Guide Zip-Front Jac-Shirt, Plaid

A rugged wool/nylon jac-shirt in malone plaid, perfect for layering with a traditional relaxed fit.

Pros: Great fit High quality Warmth Durable Comfortable fabric
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A green plaid long-sleeve shirt in a breathable cotton blend with stretch and moisture-wicking comfort.

Pros: Great looking Attractive colors Perfect fit Receives compliments
Men's Maine Guide Wool Field Shirt

A durable slate brown wool blend field shirt offering warmth, odor resistance, and a slightly fitted design.
Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit
Price was from: $89.95 now: $74.99

A rugged brown cotton flannel shirt with a cozy hood, zip front, and extra-soft brushed finish.
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
Price was from: $59.95 now: $49.99

A wrinkle-free, dark pine check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Wrinkle-free Great color Durable Comfortable Good fit

Mens Casual Winter Shirts

When the crisp air of October settles in and the days grow shorter, reaching for the right layer can make all the difference in comfort and enjoyment—whether you’re stepping out for a brisk walk, running errands around town, or gathering with friends by a backyard fire. Men’s casual winter shirts are designed with just this kind of versatility in mind, offering warmth without sacrificing ease of movement or classic style. These shirts are built to handle the demands of daily life in colder weather, crafted from hearty flannels, soft brushed twills, and other substantial fabrics that hold up to frequent wear. Details like reinforced seams, sturdy buttons, and thoughtfully placed pockets add durability and function, making these shirts a smart choice for anyone who values lasting value and timeless appeal. They’re easy to layer over a tee or under a favorite sweater, and their relaxed silhouettes mean you can stay comfortable from morning coffee runs to evening neighborhood strolls.

Choosing the best winter shirts for men often comes down to a few key considerations: warmth, comfort, and versatility. Look for shirts that feel substantial in hand—ones that offer enough insulation for chilly days, but breathe well enough to keep you comfortable indoors. Many men’s winter shirts are brushed on both sides for extra softness, making them a pleasure to pull on when the temperature drops. Patterns like classic plaids, checks, and solid earth tones not only look great, but also pair easily with jeans, cords, or even casual trousers, so you can put together a pulled-together look without overthinking it. These shirts make thoughtful gifts for dads, brothers, friends, or anyone who spends time outdoors during the colder months; they’re practical, but also carry a sense of tradition and warmth that feels just right for the season. Whether you’re heading out for a weekend hike, tackling chores around the house, or just looking for a reliable layer to keep by the door, the best mens winter shirts are the ones you’ll return to again and again.

Winter’s chill brings all kinds of opportunities to get outside and enjoy the season, and having the right casual shirts in your wardrobe can help you make the most of every moment. Quality construction ensures these shirts stand up to years of use, and thoughtful touches—like easy-to-roll sleeves and roomy fits—make them comfortable for layering or wearing on their own. For those who like to stay active even when the temperature dips, options like the Mens Walking Shirts collection offer additional choices designed for movement and all-day comfort. Whether you’re planning a weekend getaway, preparing for holiday gatherings, or simply looking to refresh your cold-weather staples, investing in the best winter shirts means you’ll be ready for whatever the season brings—inside or out.

FAQs

Men's casual winter shirts are often crafted from warm, durable materials such as flannel, heavy cotton twill, brushed cotton, and wool blends. These fabrics are chosen for their ability to provide insulation and comfort during colder months while remaining breathable and soft to the touch.

Men's casual winter shirts are incredibly versatile. For a relaxed weekend look, wear them untucked over a basic tee with jeans and boots. For a more polished appearance, tuck them into chinos and add a belt. Layering under a sweater or vest adds extra warmth and style for outdoor gatherings or casual office days.

Absolutely. Many men's winter shirts are designed with layering in mind, featuring relaxed silhouettes and soft interiors. They can be comfortably worn over t-shirts or thermal tops and easily fit under jackets or sweaters, making them ideal for adapting to changing temperatures throughout the day.

Durable winter shirts are typically reinforced with strong stitching, high-quality buttons, and sturdy fabrics that resist wear and tear. Features like double-stitched seams and reinforced elbows add extra strength, ensuring the shirt holds up to outdoor adventures, yard work, or everyday use.

Yes, men's casual winter shirts are a thoughtful and practical gift choice. Their timeless style, comfortable fit, and durable construction make them suitable for a wide range of recipients, from outdoor enthusiasts to those who appreciate classic, comfortable wardrobe staples.

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Mens Casual Winter Shirts