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Men's Winter Button Down Shirts

Explore men's winter button down shirts with classic button-front styling for your winter wardrobe. Browse the available designs and check individual shirt details for fabric, fit and sizing to find the right match for your preferences.

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Men's Signature Cord Workshirt
L.L.Bean Men's Signature Cord Workshirt
A rugged, fossil brown corduroy workshirt with nylon twill trim, perfect for versatile, untucked wear.
(0)
$119 $58.99
SALE
$119 $58.99
SALE
Men's Scotch Plaid Flannel Shirt, Traditional Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Traditional Fit
A soft, 100% Portuguese cotton flannel shirt in authentic red Scottish plaid with a relaxed fit.
(20,377)
$59.95 $59.95
SALE
What customers like:
Soft and comfortable fabric
Attractive colors and classic appearance
Warm yet lightweight
High quality and durable
Excellent fit and relaxed style
$59.95 $59.95
SALE
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
A blue houndstooth flannel shirt made from ultra-soft, shrink-resistant 100% cotton.
(8,393)
$79.95 $79.95
SALE
What customers like:
Exceptionally soft and cozy fabric
Comfortable and true-to-size fit
Wrinkle-free and easy to care for
Attractive color and stylish pattern
Durable and well-made construction
$79.95 $79.95
SALE
Men's Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
An extra-large, apple cinnamon plaid shirt made from 7.5 oz. Portuguese cotton flannel for exceptional warmth.
(7,285)
$84.95 $84.95
SALE
What customers like:
Great fit
High quality
Very comfortable
Exceptional warmth
Durable
$84.95 $84.95
SALE
Men's Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A tan, heavyweight Portuguese cotton flannel shirt with exceptional softness, double-stitched seams, and unbreakable buttons.
(7,136)
$79.95 $79.95
SALE
$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 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 button-down shirt made from wrinkle-free, moisture-wicking 100% cotton poplin for lasting comfort.
(4,814)
$69.95 $69.95
SALE
What customers like:
Comfortable fit and feel
Classic, versatile style
High quality and durable fabric
Wrinkle-free and easy care
Attractive color and pattern options
$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 supersoft, fleece-lined flannel shirt in black watch plaid, offering a relaxed traditional fit.
(4,535)
$99.95 $99.95
SALE
What customers like:
Quality
Comfort
Warmth
Softness
Versatility
$99.95 $99.95
SALE
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
L.L.Bean 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.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Versatile
Sharp look
$79.95 $79.95
SALE
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
A wrinkle-free cotton oxford shirt in French blue stripes, offering a relaxed traditional fit.
(2,141)
$64.95 $64.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Classic style
Comfortable
$64.95 $64.95
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 100% cotton offers a wrinkle-free, ultrasmooth finish and traditional fit.
(2,091)
$79.95 $79.95
SALE
What customers like:
Durable construction
Wrinkle-free quality
High-quality materials
Professional look
Comfortable fit
$79.95 $79.95
SALE
Men's Scotch Plaid Flannel Shirt, Slim Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slim Fit
A slim-fit flannel shirt in authentic Grey Stewart tartan, made from high-quality Portuguese cotton.
(1,791)
$59.95 $59.95
SALE
What customers like:
Rich colors and patterns
Perfect fit
Soft and comfortable
High-quality cotton
Warm and durable
$59.95 $59.95
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 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 Portuguese cotton for vintage-inspired comfort and style.
(1,273)
$89 $75.99
SALE
$89 $75.99
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 a rich slub texture, yarn-dyed plaid, and extra-soft finish.
(531)
$79.95 $67.99
SALE
$79.95 $67.99
SALE
Men's Maine Guide Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Shirt with PrimaLoft
A warm, durable wool blend shirt with PrimaLoft, featuring a traditional fit and check pattern.
(386)
$190 $190
SALE
What customers like:
Great fit
Excellent quality
Warmth
Durable
Comfortable
$190 $190
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 $54.99
SALE
What customers like:
Easy care
Perfect fit
Stylish design
Comfortable stretch
Great fabric
$74.95 $54.99
SALE
Men's Maine Guide Zip-Front Jac-Shirt, Plaid
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt, Plaid
A rugged multi-color plaid wool/nylon jac-shirt with ultrasuede trim, brass zipper, and reinforced pockets.
(202)
$200 $200
SALE
$200 $200
SALE
Men's Maine Guide Zip-Front Jac-Shirt
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt
A versatile wool/nylon jac-shirt with a relaxed fit, ideal for layering or wearing solo year-round.
(126)
$190 $190
SALE
$190 $190
SALE
Men's Maine Guide Lightweight Wool Field Shirt, Plaid
L.L.Bean Men's Maine Guide Lightweight Wool Field Shirt, Plaid
A forest shade plaid shirt made from a durable, odor-resistant wool blend with snap closures.
(87)
$140 $140
SALE
$140 $140
SALE
Men's Double L Field Shirt, Hunter Orange
L.L.Bean Men's Double L Field Shirt, Hunter Orange
A rugged, slightly fitted upland shirt in hunter orange cotton acrylic with reinforced forearms and bi-swing articulation.
(81)
$89.95 $89.95
SALE
What customers like:
High quality
Warmth
Durable stitching
Good fit
Excellent cuff design
$89.95 $89.95
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 $64.99
SALE
$99.95 $64.99
SALE
Men's Signature Donegal Woven Shirt, Long-Sleeve
L.L.Bean Men's Signature Donegal Woven Shirt, Long-Sleeve
A rugged gray heather shirt with Donegal flecks, crafted from 100% cotton twill flannel.
(0)
$79.95 $59.99
SALE
$79.95 $59.99
SALE

Men's Winter Button Down Shirts

Men's Winter Button Down Shirts bring a familiar, timeless look to a seasonal wardrobe, with plenty of room for personal style. There’s something appealing about the simple details of a button-down: the line of the collar, the placement of a pocket, the pattern running across the front. When choosing a shirt, start with the look you already enjoy rather than something that calls for a whole new wardrobe. A small-scale check has a different character than a bold plaid, while a solid color lets the shape and details take the lead. Think about the colors you reach for most often and how much contrast you like. Deep shades, understated neutrals and brighter patterns each offer a different way to make a familiar style your own. The goal is a shirt that feels like a natural addition to your closet—not one you have to talk yourself into wearing.

Fit deserves just as much attention as color and pattern. Before choosing a size, check the individual shirt’s measurements and fit description rather than relying on the size you usually buy. A favorite shirt you already own is a useful point of reference: lay it flat and compare its chest width, shoulder width, sleeve length and overall length with the measurements provided, making sure you follow the same measuring method. Consider whether you prefer a closer shape or a roomier silhouette, and look at the hem if you have a preference for wearing shirts tucked or untucked. Collar proportions, cuffs and pocket arrangements are worth a closer look, too. These details can seem small in a photograph, yet they often explain why one shirt becomes a favorite and another stays on the hanger. Read the care instructions before deciding, so you know what each shirt needs and whether that fits your routine.

For a gift, a winter button-down shirt is a chance to show that you’ve noticed someone’s individual taste. Picture the shirts your partner, father, brother or friend chooses again and again: perhaps there’s always a quiet check in the mix, or a preference for solid colors and minimal detailing. Let those familiar choices guide you. If you can, confirm the recipient’s preferred size and fit instead of guessing, and remember that two shirts with the same size label may have different measurements. A pattern close to an existing favorite can feel thoughtful without being an exact repeat; a different shade can add variety while staying true to their style. Whether you’re choosing a gift or refreshing your own selection, take time to compare the details that matter most. A considered choice begins with knowing the person who will wear it.

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