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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 Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
L.L.Bean Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted
A green plaid flannel shirt featuring soft Sherpa fleece lining and taffeta-lined sleeves for warmth and comfort.
(2,758)
$130 $130
SALE
$130 $130
SALE
Men's Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
A gray plaid shirt crafted from heavyweight Portuguese flannel for exceptional warmth and softness.
(7,285)
$84.95 $84.95
SALE
What customers like:
Warm and substantial heavyweight fabric
High quality and durable construction
Attractive colors and patterns
Exceptionally soft and comfortable
True to size with a good fit
$84.95 $84.95
SALE
Men's Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A tan, heavyweight flannel shirt crafted from ultra-soft Portuguese cotton with durable double-stitched seams.
(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 brown wool-blend Henley with duofold construction for warmth and a relaxed, traditional fit.
(6,147)
$79.95 $67.99
SALE
What customers like:
Soft material
Warm and cozy
High quality and durable
Versatile for cold weather
Comfortable fit
$79.95 $67.99
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
A red check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.
(1,619)
$69.95 $69.95
SALE
What customers like:
Attractive color and style
Lightweight and breathable
High quality material
Wrinkle-free fabric
Comfortable fit
$69.95 $69.95
SALE
Men's Katahdin Performance Flannel Shirt, Slightly Fitted
L.L.Bean Men's Katahdin Performance Flannel Shirt, Slightly Fitted
A multi-color plaid flannel shirt made from quick-drying, water-repellent polyester and wool blend.
(1,345)
$99.95 $84.99
SALE
What customers like:
Durable and high quality
Stylish appearance and vibrant colors
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 crafted from soft, garment-washed Portuguese cotton for vintage comfort.
(1,273)
$89 $75.99
SALE
$89 $75.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
L.L.Bean 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.
(1,214)
$69.95 $49.99
SALE
What customers like:
Great fit
High quality
Attractive color
Versatile design
Excellent comfort
$69.95 $49.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
L.L.Bean 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.
(1,159)
$74.95 $54.99
SALE
What customers like:
High quality material
Well made
Good stretch
Soft fabric
Comfortable fit
$74.95 $54.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid
A rugged white cotton flannel shirt with rich slub texture, brushed for extra softness and durability.
(531)
$79.95 $67.99
SALE
$79.95 $67.99
SALE
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
A breathable blue cotton-blend chambray shirt with built-in stretch and a moisture-wicking, untucked design.
(267)
$74.95 $62.99
SALE
What customers like:
Easy care
Perfect fit
Stylish design
Comfortable stretch
Great fabric
$74.95 $62.99
SALE
Men's Signature Wool Workshirt
L.L.Bean Men's Signature Wool Workshirt
A rugged gray wool-blend workshirt with twill trim and buttoned pockets for lasting warmth and durability.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit, Plaid
L.L.Bean 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.
(0)
$69.95 $54.99
SALE
$69.95 $54.99
SALE
Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit
L.L.Bean Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit
A brown cotton flannel shirt with a soft jersey-knit lining, designed for untucked, slightly fitted comfort.
(0)
$99.95 $74.99
SALE
$99.95 $74.99
SALE
Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit, Plaid
A white, midweight cotton flannel shirt with a cozy hood, zip front, and durable triple-needle stitching.
(0)
$89.95 $75.99
SALE
$89.95 $75.99
SALE
Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit
L.L.Bean Men's 1912 Field Flannel Shirt, Hooded, Slightly Fitted Untucked Fit
A rugged brown cotton flannel shirt with a cozy hood, zip front, and extra-soft brushed finish.
(0)
$89.95 $66.99
SALE
$89.95 $66.99
SALE
Men's Quilted Scotch Plaid Flannel Shirt Jac
L.L.Bean Men's Quilted Scotch Plaid Flannel Shirt Jac
A lightly insulated Portuguese cotton flannel shirt jac with quilted texture and authentic yarn-dyed tartan colors.
(0)
$120 $89.99
SALE
$120 $89.99
SALE
Men's Maine Guide Lightweight Lined Wool Field Shirt, Plaid
L.L.Bean Men's Maine Guide Lightweight Lined Wool Field Shirt, Plaid
A red wool-blend plaid shirt with grid fleece lining, offering warmth, durability, and classic style.
(0)
$160 $160
SALE
$160 $160
SALE
Men's Katahdin Performance Flannel Shirt
L.L.Bean Men's Katahdin Performance Flannel Shirt
A red wool-blend flannel shirt featuring quick-drying, water-repellent fabric and reinforced elbows for durability.
(0)
$99.95 $74.99
SALE
$99.95 $74.99
SALE
Men's 1933 Chamois Cloth Shirt, Slim Fit
L.L.Bean Men's 1933 Chamois Cloth Shirt, Slim Fit
A slim-fitting brown shirt crafted from soft, vintage-washed 100% cotton chamois flannel.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Long-Sleeve, Slim Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Long-Sleeve, Slim Fit, Check
A slim-fit blue check shirt made of wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
SALE
Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit
L.L.Bean Men's Sunwashed Corduroy Shirt, Slightly Fitted Untucked Fit
A superlight white cotton corduroy shirt with a vintage look, untucked fit, and lived-in softness.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit
A rugged midweight brown flannel shirt with a slightly fitted untucked fit, crafted from 100% cotton.
(0)
$79.95 $64.99
SALE
$79.95 $64.99
SALE
Men's 1933 Chamois Cloth Shirt, Slim Fit, Print
L.L.Bean Men's 1933 Chamois Cloth Shirt, Slim Fit, Print
A slim-fit brown chamois flannel shirt crafted from soft, vintage-washed 100% cotton with angled flap pockets.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
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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