Men's Winter Button Down Shirts

When cold weather arrives, mens winter button down shirts are an essential part of any wardrobe. These shirts bring together classic style and reliable comfort, making it easy to layer up for warmth while maintaining a polished look. Whether you’re heading out for a brisk walk or gathering with friends by the fire, our collection offers versatile options designed to keep you feeling your best all season long. With timeless patterns and practical details, these shirts are ready for everything winter has in store.

Sort by:

Filter & Sort

476 Items

Men's Scotch Plaid Flannel Shirt, Traditional Fit

An indigo tartan flannel shirt made from high-quality Portuguese cotton with a relaxed traditional fit.

Pros: Perfect fit Well-made Softness Warmth Comfortable
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A charcoal heather flannel shirt with sheepskin shearling lining, offering superior softness and traditional fit.

Pros: Beautiful design Roomy fit Warmth Durable Superior softness
Men's Chamois Shirt, Traditional Fit, Plaid
Price was from: $84.95 now: $69.99

A heavyweight plaid flannel shirt in barley, made from 7.5 oz. Portuguese cotton for exceptional warmth.

Pros: Exceptional softness High quality fabric Durable construction Attractive color and pattern Great warmth
Men's Chamois Shirt, Traditional Fit

A tan, heavyweight Portuguese cotton flannel shirt with exceptional softness, double-stitched seams, and unbreakable buttons.
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A red check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Comfortable and soft material Classic style with versatile color options High quality and durable fabric Wrinkle-free and easy care Excellent fit and accurate sizing
Men's Fleece-Lined Flannel Shirt, Traditional Fit

A supersoft, fleece-lined flannel shirt in black watch plaid, offering a relaxed traditional fit.

Pros: Quality Comfort Warmth Softness Versatility
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $69.95 now: $58.99

A slightly fitted, wrinkle-free cotton sport shirt in blue check with moisture-wicking TrueCool® fabric.

Pros: Great fit Versatile color Attractive look Stylish design Comfortable to wear
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 Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $54.99

A soft, midweight cotton flannel shirt in light gray heather with a slim fit and durable stitching.

Pros: High quality Perfect fit Lighter weight True to size Versatile
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged white cotton flannel shirt with a rich slub texture, yarn-dyed plaid, and extra-soft finish.
Men's Maine Guide Shirt with PrimaLoft

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

Pros: Great fit High quality Comfortable Stylish appearance Excellent warmth
Men's Scotch Plaid Flannel Shirt, Snap-Front, Slightly Fitted Untucked Fit

A blue Portuguese cotton flannel shirt with snap-front, corduroy details, and authentic yarn-dyed tartan.
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged gray heather shirt with Donegal flecks, crafted from 100% cotton twill flannel.
Men's Maine Guide Lightweight Wool Field Shirt

A durable slate brown flannel shirt made from a warm wool blend, featuring a 7-snap front and chest pockets.
Men's Signature Wool Workshirt, Plaid
Price was from: $159 now: $134.99

A rugged brown plaid workshirt crafted from a durable wool-blend with twill and flannel trim details.
Men's Brushed Jaspé Twill Shirt, Plaid, Traditional Untucked Fit
Price was from: $69.95 now: $44.99

A green plaid shirt crafted from 100% cotton jaspé yarns, offering a relaxed untucked fit.
Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit
Price was from: $99.95 now: $84.99

A brown cotton flannel shirt with a soft jersey-knit lining, designed for comfort and untucked style.
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit
Price was from: $79.95 now: $54.99

A rugged brown cotton flannel shirt with a soft brushed finish and durable triple-needle stitching.
Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit, Plaid
Price was from: $110 now: $92.99

A rugged brown plaid flannel shirt with a soft jersey-knit cotton lining and durable triple-needle stitching.
Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley

A brown wool-blend Henley with duofold construction for warmth and a relaxed, traditional fit.

Pros: Very comfortable Soft, non-scratchy material Warm and cozy for cold weather High quality and durable Fits well and true to size
Men's Sunwashed Canvas Shirt, Traditional Fit

A cadet blue, 100% cotton canvas shirt with a relaxed fit and durable double-needle stitching.

Pros: High quality Durable construction Versatile for spring and fall Great color options Comfortable fit
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free blue cotton shirt with a traditional fit, offering a freshly pressed look without ironing.

Pros: High quality Perfect fit Wrinkle-free Versatile Sharp look
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

A wrinkle-free, 100% cotton tattersall shirt in crystal blue with a traditional fit for all-day comfort.

Pros: High quality Wrinkle-free Easy to care for Durable Comfortable fit
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $75.99

A slim-fit brown plaid flannel shirt crafted from soft, garment-washed Portuguese cotton for vintage comfort.

Pros: Warm and heavyweight material Soft and comfortable fabric Flattering slim fit Attractive color and pattern High quality construction

Men's Winter Button Down Shirts

When winter settles in and the days grow shorter, men’s winter button down shirts quickly become a staple for staying comfortable and put-together, whether you’re heading out for a brisk walk, meeting friends at a cozy café, or simply relaxing by the fire. These shirts are thoughtfully designed to handle the demands of the season, offering warmth without bulk and allowing for effortless layering under a sweater, fleece, or jacket. With fabrics like soft brushed flannel, rugged twill, and hearty cotton blends, winter button downs are built to keep the chill at bay while feeling gentle against the skin. Many feature details like double-stitched seams, reinforced collars, and practical chest pockets—details that speak to their lasting value and everyday utility. The timeless style of a button down makes it a versatile choice for all kinds of winter activities, from chopping wood on a frosty morning to enjoying a weekend getaway in the mountains. It’s these thoughtful touches and classic good looks that make them an essential part of any winter wardrobe.

Men’s winter button down shirts also make a thoughtful and appreciated gift, especially during the colder months when comfort and durability matter most. They’re a go-to option for sons heading back to campus, dads who appreciate a shirt that feels as good as it looks, or friends who love spending time outdoors. With a wide range of colors, patterns, and sizes, it’s easy to find a shirt that matches anyone’s personal style and fits right into their day-to-day routine. Whether worn on their own, layered over a favorite tee, or paired with a warm vest, these shirts are as suitable for a casual office as they are for a weekend adventure. The adaptable nature of a button down means it transitions seamlessly from weekday to weekend, from outdoor pursuits to indoor gatherings. When you’re choosing a shirt for winter, look for features like easy-care fabrics, generous cuts for layering, and time-tested construction that stands up to repeated wear and washing. For those who spend a lot of time outside, options with moisture-wicking properties and heavier weights add extra comfort and practicality. If you’re interested in exploring more options designed for the outdoors, take a look at our selection of Men's Outdoor Button Down Shirts for even more rugged, reliable choices.

The beauty of men’s winter button down shirts lies in their ability to bring together comfort, durability, and timeless style. They’re the kind of shirts you reach for again and again—whether you’re layering up for a snowy hike, heading into town for errands, or simply enjoying a quiet evening at home. Their classic silhouettes and reliable construction mean they’ll be a favorite season after season, ready to take on whatever winter brings. With each wash and wear, they become even more comfortable, offering the kind of lasting value that’s always appreciated. In the heart of January, when warmth and versatility matter most, these shirts stand out as a practical, dependable, and always stylish choice for any man’s closet.

FAQs

Men's winter button down shirts are often crafted from warm, comfortable materials such as brushed flannel, heavyweight cotton, or soft twill. These fabrics provide insulation against the cold while remaining breathable, making them ideal for layering during winter months.

A winter button down shirt is incredibly versatile. For casual days, wear it over a long-sleeve tee or thermal, paired with jeans and boots. For a more polished look, layer it under a sweater or a vest and combine with chinos. The classic design works well for both relaxed weekends and gatherings with family or friends.

Yes, many men's winter button down shirts are designed with outdoor use in mind. Features like durable stitching, reinforced elbows, and moisture-wicking fabrics make them a practical choice for hiking, camping, or spending time around a campfire.

Traditional plaids, checks, and solid earth tones are especially popular for winter button down shirts. These patterns and colors not only evoke a classic, outdoorsy feel but also pair easily with other winter wardrobe staples.

Absolutely. Winter button down shirts are designed to be easy to layer. They work well under sweaters, fleeces, or insulated jackets, and can also be worn open over a thermal or henley for added warmth and style.

It's time to upgrade your browser

Men's Winter Button Down Shirts