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Mens Casual Winter Shirts

Find men's casual winter shirts that bring classic, easygoing style to your winter wardrobe. Browse the selection and compare fit, color and design details to choose shirts that suit your everyday style.

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Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
A gray houndstooth flannel shirt in brushed cotton, shearling-lined for warmth, resisting shrinkage, wrinkles and pilling.
(8,393)
$79.95 $79.95
SALE
What customers like:
Beautiful design
Roomy fit
Warmth
Durable
Superior softness
$79.95 $79.95
SALE
Men's Fleece-Lined Flannel Shirt, Traditional Fit, Plaid
L.L.Bean Men's Fleece-Lined Flannel Shirt, Traditional Fit, Plaid
A blue plaid shirt in brushed cotton flannel with a warm polyester fleece lining and convenient chest and side pockets.
(4,535)
$99.95 $99.95
SALE
What customers like:
Quality
Comfort
Warmth
Softness
Versatility
$99.95 $99.95
SALE
Men's Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
A warm brown plaid chamois flannel shirt, brushed for softness and built with rugged double-stitched durability.
(7,285)
$84.95 $84.95
SALE
$84.95 $84.95
SALE
Men's Fleece-Lined Flannel Shirt, Traditional Fit
L.L.Bean Men's Fleece-Lined Flannel Shirt, Traditional Fit
A tan men's flannel shirt with soft cotton exterior, cozy polyester fleece lining, and practical pockets.
(0)
$99.95 $99.95
SALE
$99.95 $99.95
SALE
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slightly Fitted
A slightly fitted men’s white plaid shirt in soft 100% cotton Portuguese flannel, with a button-down collar.
(6,433)
$59.95 $29.99
SALE
What customers like:
High quality
Attractive design
Softness
Warmth
Comfortable fit
$59.95 $29.99
SALE
Men's Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A tan men's chamois flannel shirt, brushed for softness, with durable double-stitched seams and unbreakable buttons.
(7,136)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Men's Two-Layer River Driver's Shirt®, Traditional Fit, Henley
L.L.Bean Men's Two-Layer River Driver's Shirt®, Traditional Fit, Henley
A purple two-layer Henley shirt with cotton and wool-blend construction that traps warmth and dries quickly.
(6,147)
$79.95 $79.95
SALE
What customers like:
Good quality
Warmth
True to size
Comfortable fit
Versatility
$79.95 $79.95
SALE
Men's Premium Double L® Polo, Long-Sleeve Without Pocket
L.L.Bean Men's Premium Double L® Polo, Long-Sleeve Without Pocket
A supersoft green cotton long-sleeve polo that resists wrinkling, fading, shrinking, and pilling.
(5,065)
$54.95 $44.99
SALE
What customers like:
Durable and warm
High quality
Attractive color options
Soft fabric
Comfortable fit
$54.95 $44.99
SALE
Men's Unshrinkable Mini-Waffle Henley, Traditional Fit, Long-Sleeve
L.L.Bean Men's Unshrinkable Mini-Waffle Henley, Traditional Fit, Long-Sleeve
A brown cotton mini-waffle thermal with three-button neckline, designed to resist shrinking, fading and pilling.
(4,807)
$69.95 $69.95
SALE
What customers like:
Attractive design
High quality material
Warm and cozy
True to size
Comfortable fit
$69.95 $69.95
SALE
Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
L.L.Bean Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
A green plaid flannel shirt with an ultrawarm Sherpa lining, snap front, and convenient pockets.
(2,758)
$130 $130
SALE
$130 $130
SALE
Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
A gray men’s flannel shirt with shearling lining, houndstooth pattern, button-down collar and wrinkle-resistant cotton.
(2,582)
$79.95 $79.95
SALE
What customers like:
High quality
Soft material
Stylish design
Warmth
Comfortable fit
$79.95 $79.95
SALE
Men's Katahdin Iron Works® Bonded Waffle Fleece Henley
L.L.Bean Men's Katahdin Iron Works® Bonded Waffle Fleece Henley
A gray waffle-knit henley with plush berber fleece lining, bonded insulation, and a secure chest pocket.
(2,237)
$89.95 $89.95
SALE
What customers like:
Great fit
High quality
Warmth
Versatile
Comfortable
$89.95 $89.95
SALE
Men's Katahdin Performance Flannel Shirt, Slightly Fitted
L.L.Bean Men's Katahdin Performance Flannel Shirt, Slightly Fitted
A plaid flannel shirt in quick-drying, water-repellent polyester-wool blend with reinforced elbows and snap front.
(1,345)
$99.95 $84.99
SALE
What customers like:
Stylish appearance and vibrant colors
Durable and well made
Warm and comfortable
Easy care and quick drying
Convenient snap closures
$99.95 $84.99
SALE
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
L.L.Bean Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
A slim-fit brown plaid flannel shirt in brushed 100% cotton, garment-washed for exceptional softness and comfort.
(1,273)
$89 $75.99
SALE
$89 $75.99
SALE
Men's Signature Waffle Crew
L.L.Bean Men's Signature Waffle Crew
A brown cotton waffle-knit thermal crewneck shirt with raglan sleeves and rib-knit cuffs for comfortable layering.
(692)
$89 $59.99
SALE
What customers like:
Good fit when sized down
Attractive color
Warmth
Excellent quality
Comfortable and soft
$89 $59.99
SALE
Men's Maine Guide Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Shirt with PrimaLoft
A warm multicolor checked wool-nylon shirt with PrimaLoft insulation, durable construction and a relaxed layering fit.
(386)
$190 $190
SALE
What customers like:
Great fit
Excellent quality
Warm and comfortable
Durable material
Stylish appearance
$190 $190
SALE
Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft, Plaid
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft, Plaid
A gray plaid wool-nylon jac-shirt with windproof PrimaLoft insulation, rugged brass zipper and handwarmer pockets.
(303)
$250 $250
SALE
What customers like:
Very comfortable
Durable construction
Excellent warmth
$250 $250
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve, Stripe
A blue striped chambray shirt in a moisture-wicking cotton blend with stretch and a traditional fit.
(267)
$74.95 $54.99
SALE
What customers like:
Easy care
Perfect fit
Stylish design
Comfortable stretch
Great fabric
$74.95 $54.99
SALE
Men's Tropicwear Shirt, Plaid Long-Sleeve
L.L.Bean Men's Tropicwear Shirt, Plaid Long-Sleeve
A brown plaid long-sleeve shirt in recycled polyester blend with UPF 50+ protection and venting.
(159)
$79.95 $59.99
SALE
What customers like:
High quality
Effective sunblock
Well-made
Cool and comfortable fabric
Good fit
$79.95 $59.99
SALE
Men's Maine Guide Zip-Front Jac-Shirt, Plaid
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt, Plaid
A gray plaid wool-nylon jac-shirt with a rugged brass zipper, exterior cape, and handwarmer pockets.
(202)
$200 $200
SALE
What customers like:
Great fit
High quality
Warmth
Durable
Comfortable fabric
$200 $200
SALE
Men's Stonecoast Hemp Shirt, Slightly Fitted, Long-Sleeve, Stripe
L.L.Bean Men's Stonecoast Hemp Shirt, Slightly Fitted, Long-Sleeve, Stripe
A gray striped long-sleeve shirt in a soft, durable hemp-cotton blend with stretch and chest pockets.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Men's Maine Guide Zip-Front Jac-Shirt
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt
A brown wool-nylon jac-shirt with a rugged brass zipper, cape, and handwarmer pockets for versatile warmth.
(126)
$190 $190
SALE
$190 $190
SALE
Men's Signature Stretch Poplin Shirt, Slim Fit, Long-Sleeve
L.L.Bean Men's Signature Stretch Poplin Shirt, Slim Fit, Long-Sleeve
A tan slim-fit long-sleeve shirt in stretch cotton poplin, featuring a button-down collar and chest pocket.
(0)
$79 $29.99
SALE
$79 $29.99
SALE
Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft
A brown wool-blend jac-shirt with windproof PrimaLoft insulation, exterior cape, and rugged zip-front design for warmth.
(117)
$240 $240
SALE
What customers like:
Very warm
Good fit
Comfortable to wear
$240 $240
SALE

Mens Casual Winter Shirts

Casual winter style has a familiar appeal: a favorite shirt, an easygoing outfit, and a little less time spent deciding what to wear. The Mens Casual Winter Shirts collection is a place to explore that everyday approach to getting dressed, with an eye toward personal style rather than passing trends. When choosing a shirt, start with the pieces already in your closet. Think about the jeans you reach for most often, the pants you prefer for a casual get-together, and the colors that feel most like you. A subtle pattern can bring interest to a simple outfit, while a solid color leaves room for other details to stand out. Pay attention to the collar, pockets, buttons, and hem, too. Those small choices help determine whether a shirt has the relaxed character or slightly more polished look you want.

Fit deserves just as much consideration as appearance, especially when you’re choosing a winter shirt online. A useful starting point is a shirt you already own and enjoy wearing: compare its measurements with the available sizing information, and consider what you like about the way it sits at the shoulders and falls through the body. Read each item’s fit description rather than relying on size alone. Think about whether you prefer a closer silhouette or a roomier shape, and whether you usually wear your shirts tucked or untucked. Length matters here; a hem that looks right one way may not suit your preference the other. If wearing another piece underneath is part of your winter routine, keep that preference in mind as you compare measurements. Check individual care instructions as well, so the shirt you choose fits your laundry habits along with your wardrobe. The goal is a choice that feels considered without making getting dressed complicated.

Men’s casual winter shirts can also make thoughtful gifts when the choice reflects the recipient’s own taste. Picture the shirts a partner, father, brother, or friend wears again and again—not just their colors, but their patterns, proportions, and details. Someone who favors understated clothing may appreciate a familiar shade more than a bold departure, while a person who regularly wears checks may welcome another interpretation of that look. Confirm sizing when possible, and resist choosing a different fit simply because it happens to be your preference. The most personal gift often comes from noticing something ordinary: a favorite collar style, a consistently untucked hem, or a wardrobe full of quiet blues and greens. Whether you’re shopping for someone else or rounding out your own winter wardrobe, choosing with those everyday preferences in mind is a straightforward way to find a shirt that belongs in the regular rotation.

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