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.

Sort by:

Filter & Sort

298 Items

Men's Chamois Shirt, Traditional Fit, Plaid

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 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 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 Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
Price was from: $79.95 now: $54.99

A katahdin khaki houndstooth flannel shirt offering superior softness, warmth, and resistance to shrinking and wrinkling.

Pros: Great quality Warm and cozy Excellent fit Superior softness Beautiful color
Men's Chamois Shirt, Traditional Fit

A heavyweight brown flannel shirt crafted from ultra-soft Portuguese cotton with durable double-stitched seams.
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 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 1912 Heritage Lined Shirt Jac, Corduroy
Price was from: $119 now: $89.99

A walnut-colored corduroy shirt jacket with ultrasoft berber fleece lining and durable triple-needle stitching.

Pros: Perfect for fall Well-made Warmth Comfortable fit Classic design
Men's Katahdin Performance Flannel Shirt, Slightly Fitted
Price was from: $99.95 now: $59.99

A slightly fitted, quick-drying flannel shirt in deep red or shale gray with reinforced elbows and snap front.

Pros: High quality fabric Stylish design Comfort Warmth Durable
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $59.99

A slim-fit plaid shirt in golden cider, made from 100% cotton flannel for vintage softness.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

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

Pros: Great fit High quality Attractive color Versatile design Excellent comfort
Men's Fleece-Lined Flannel Shirt, Snap Front, Slightly Fitted
Price was from: $89 now: $69.99

A cozy, fleece-lined flannel shirt with snap front, side pockets, and a slightly fitted design.

Pros: Soft material Durable quality Versatile design Excellent warmth Comfortable fit
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 Scotch Plaid Flannel Hooded Shirt, Slightly Fitted
Price was from: $89 now: $69.99

A slightly fitted vintage red Rob Roy flannel shirt with a hood, made from high-quality Portuguese cotton.

Pros: Perfect fit Great quality Well-made Warm and cozy Comfortable
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 Chamois Shirt, Slightly Fitted, Plaid
Price was from: $84.95 now: $64.99

A slightly fitted, heavy-weight chamois flannel shirt in barley, made from 7.5 oz. Portuguese cotton.

Pros: Perfect fit Excellent quality Warmth Comfortable Versatility
Men's Chamois Shirt, Slightly Fitted

A brown, slightly fitted shirt crafted from thick Portuguese cotton flannel for exceptional warmth and softness.
Men's Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $39.99

A soft, midweight cotton flannel shirt in American Khaki, featuring a slim fit and durable triple-needle stitching.

Pros: High quality Perfect fit Colorful True to size Versatile
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 Maine Guide Shirt with PrimaLoft

A warm PrimaLoft wool blend shirt in cobalt and black, perfect for layering with a relaxed fit.

Pros: Great fit Excellent quality Warmth Comfortable Stylish appearance
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 Maine Guide Zip-Front Jac-Shirt, Plaid

A rugged red and black plaid jac-shirt made from 85% wool and 15% nylon, perfect for layering.

Pros: Great fit High quality Warmth Durable Comfortable fabric
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A green plaid long-sleeve shirt in a breathable cotton blend with stretch and moisture-wicking comfort.
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged cream twill flannel shirt with Donegal flecks, slim fit, and button-down collar.

Mens Casual Winter Shirts

When the air turns crisp and the days grow shorter, a dependable collection of men’s casual winter shirts quickly becomes a staple in any cold-weather wardrobe. Whether you’re layering up for a snowy morning walk, heading to the office, or gathering around the fire with friends, these shirts are designed to offer both comfort and lasting value through every winter adventure. Crafted from durable, easy-care fabrics like flannel, brushed cotton, or soft twill, they stand up to frequent wear and washing, making them a practical choice for daily use. The relaxed, timeless styles blend seamlessly with jeans, chinos, or corduroys, so it’s easy to transition from a weekend hike to an evening out without missing a beat. Many men appreciate the versatility these shirts provide—wear them buttoned up for extra warmth, or layer them over a favorite tee for a laid-back look that’s ready for anything. The right casual winter shirt feels just as at home by the woodpile as it does at a casual dinner, and with a wide range of patterns, colors, and sizes, there’s an option for everyone.

These shirts also make thoughtful gifts for the men in your life, especially as the holiday season approaches. A well-made winter shirt is the kind of gift that gets used right away—ideal for brothers, dads, uncles, or friends who appreciate comfort and quality. If you’re shopping for someone who spends a lot of time outdoors, look for shirts with features like double-stitched seams, sturdy buttons, and generous pockets for stashing gloves or a phone. For those who value easy care, wrinkle-resistant fabrics are a welcome touch, keeping them looking sharp with minimal effort. And for anyone who tends to run cold, consider exploring heavier options such as those featured on our Mens Thick Winter Shirts page, where added warmth meets classic style. Whether worn alone or as a mid-layer beneath a favorite jacket, these shirts offer reliable comfort that lasts well beyond the winter months.

As you prepare for the colder days ahead, it’s worth considering how a few well-chosen casual winter shirts can add both function and style to your seasonal rotation. Picture an early morning spent watching the snow fall, wrapped in a soft flannel shirt, or a weekend getaway where a favorite plaid becomes the go-to layer for everything from breakfast at the cabin to an evening stroll. These shirts are designed to be easy to wear and even easier to care for, making them perfect for busy schedules and spontaneous plans alike. With details like button-down collars, chest pockets, and relaxed cuffs, they combine rugged durability with a comfortable fit that feels just right all day long. No matter how you spend your winter—whether it’s tackling outdoor projects, enjoying family gatherings, or simply savoring the quiet moments—men’s casual winter shirts are built to keep you warm, comfortable, and ready for whatever the season brings.