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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 Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A heavy-weight charcoal gray heather flannel shirt, perfect as a light jacket or essential layering piece.
(7,136)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Warmth
Versatile
Comfortable
$79.95 $79.95
SALE
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slightly Fitted
A slightly fitted green plaid shirt made from high-quality Portuguese cotton flannel with a button-down collar.
(6,433)
$59.95 $59.95
SALE
What customers like:
Quality construction
Perfect fit
Softness
Warmth
Comfortable
$59.95 $59.95
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 featuring soft Sherpa fleece lining and taffeta-lined sleeves for warmth and comfort.
(2,758)
$130 $130
SALE
$130 $130
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 cotton blend shirt with built-in stretch, perfect for untucked wear and easy movement.
(1,214)
$69.95 $49.99
SALE
What customers like:
Great fit
High quality
Versatile design
Excellent comfort
Soft fabric
$69.95 $49.99
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit
A tan 100% cotton canvas shirt with a relaxed fit, durable stitching, and button-flap pockets.
(5,386)
$69.95 $69.95
SALE
What customers like:
High quality
Soft material
Durable construction
Versatile design
Comfortable fit
$69.95 $69.95
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 $44.99
SALE
What customers like:
No ironing required
Attractive color and style
High-quality construction
Wrinkle-free fabric
Comfortable fit
$69.95 $44.99
SALE
Men's Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
A heavy-weight, ultra-soft plaid flannel shirt in barley, perfect for layering with a relaxed traditional fit.
(7,285)
$84.95 $41.99
SALE
What customers like:
High quality
Attractive color
Softness
Warmth
Comfortable fit
$84.95 $41.99
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:
Very comfortable
Soft, non-scratchy material
Warm and cozy for cold weather
High quality and durable
Fits well and true to size
$79.95 $67.99
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
A red check cotton poplin shirt offering wrinkle-free performance, moisture-wicking comfort, and classic button-down style.
(4,814)
$69.95 $69.95
SALE
What customers like:
Comfortable fit and feel
High quality and durable fabric
Wrinkle-free and easy care
Attractive colors and pattern
Classic style and versatile design
$69.95 $69.95
SALE
Men's Unshrinkable Mini-Waffle Henley, Long-Sleeve Traditional Fit
L.L.Bean Men's Unshrinkable Mini-Waffle Henley, Long-Sleeve Traditional Fit
A brown, 100% cotton long-sleeve henley that resists shrinking, fading, and pilling wash after wash.
(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 Fleece-Lined Flannel Shirt, Traditional Fit, Plaid
L.L.Bean Men's Fleece-Lined Flannel Shirt, Traditional Fit, Plaid
A supercozy chalk blue plaid flannel shirt with a fleece lining, relaxed fit, and multiple pockets.
(4,535)
$99.95 $99.95
SALE
What customers like:
Quality
Comfort
Warmth
Softness
Versatility
$99.95 $99.95
SALE
Men's Quilted Sweatshirt, Mockneck
L.L.Bean Men's Quilted Sweatshirt, Mockneck
A brown quilted pullover made from a soft polyester-cotton blend with raglan sleeves and snap placket.
(2,386)
$89.95 $74.99
SALE
What customers like:
Stylish appearance and colors
Versatile for multiple seasons
High quality and durable
Warm and great for layering
Comfortable fit
$89.95 $74.99
SALE
Men's L.L.Bean Classic Ragg Wool Sweater, Henley
L.L.Bean Men's L.L.Bean Classic Ragg Wool Sweater, Henley
A midweight brown Henley sweater knit from premium lambswool for warmth and classic style.
(2,145)
$99.95 $84.99
SALE
What customers like:
High quality and well made
True to size fit
Warm and cozy
Comfortable soft material
Classic and versatile style
$99.95 $84.99
SALE
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
A blue tattersall shirt in wrinkle-free cotton offers a nearly custom fit and all-day comfort.
(2,091)
$79.95 $79.95
SALE
What customers like:
Durable and sturdy
Wrinkle-free quality
High-quality materials
Professional look
Comfortable fit
$79.95 $79.95
SALE
Men's Waterfowl Sweater
L.L.Bean Men's Waterfowl Sweater
A classic blue lambswool sweater with leather zipper pull and integrated shooting patches for durability.
(1,733)
$130 $130
SALE
What customers like:
Versatile design with useful features
Warm and toasty
High quality and durable
Comfortable fit
Attractive color and appearance
$130 $130
SALE
Men's Organic Cotton Waffle Sweater, Quarter Zip
L.L.Bean Men's Organic Cotton Waffle Sweater, Quarter Zip
A cozy tan quarter-zip sweater made from 100% organic cotton with a thick waffle-stitch knit.
(1,400)
$99.95 $84.99
SALE
What customers like:
Beautiful design
High quality
Warm and cozy
True to size
Comfortable fit
$99.95 $84.99
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 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 Signature Waffle Crew
L.L.Bean Men's Signature Waffle Crew
A slim-fitting brown crewneck pullover made from breathable, 100% waffle-knit cotton for cooler weather.
(692)
$89 $74.99
SALE
What customers like:
Good fit when sized down
Attractive color
Warmth
Excellent quality
Comfortable and soft
$89 $74.99
SALE
Men's Waterfowl Sweater with WINDSTOPPER by GORE-TEX LABS
L.L.Bean Men's Waterfowl Sweater with WINDSTOPPER by GORE-TEX LABS
A brown lambswool sweater featuring windproof, breathable WINDSTOPPER fabric and durable shooting patches.
(526)
$200 $200
SALE
What customers like:
Classic, good-looking style
Durable, high-quality fabric
True to size and great fit
Comfortable and soft lining
Warm and windproof
$200 $200
SALE
Men's Cresta Wool Midweight 250 Crew Top
L.L.Bean Men's Cresta Wool Midweight 250 Crew Top
A versatile merino wool base layer that wicks sweat, resists odor, and features thumbhole cuffs.
(489)
$99.95 $84.99
SALE
What customers like:
Great fit
Comfortable feel
Durable material
Soft fabric
Excellent warmth
$99.95 $84.99
SALE
Men's Bean's Classic Ragg Wool Sweater, Crewneck, Fair Isle
L.L.Bean Men's Bean's Classic Ragg Wool Sweater, Crewneck, Fair Isle
A tan lambswool sweater in a timeless Fair Isle pattern, offering substantial warmth without bulk.
(402)
$99.95 $84.99
SALE
What customers like:
Gorgeous design
Perfect fit
Expected quality
Comfortable wear
Substantial warmth
$99.95 $84.99
SALE
Men's Maine Guide Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Shirt with PrimaLoft
A warm PrimaLoft wool blend shirt in red and black check, ideal for layering and outdoor activities.
(386)
$190 $190
SALE
What customers like:
Great fit
Excellent quality
Warm and comfortable
Durable material
Stylish appearance
$190 $190
SALE
Men's Cresta Midweight 250 Quarter-Zip Top
L.L.Bean Men's Cresta Midweight 250 Quarter-Zip Top
A versatile midweight merino wool base layer in saddle heather, featuring a quarter-zip and thumbhole cuffs.
(375)
$120 $99.99
SALE
What customers like:
Convenience
Keeps you warm
Comfort
Durability
Versatility
$120 $99.99
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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