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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 Scotch Plaid Flannel Shirt, Traditional Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Traditional Fit
A gray plaid shirt in 100% Portuguese cotton flannel with a button-down collar and shirttail hem.
(20,377)
$59.95 $59.95
SALE
What customers like:
Well-made
Versatile style
Softness
Warmth
Comfortable fit
$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 gray houndstooth cotton flannel shirt with cozy shearling lining, a button-down collar, and wrinkle resistance.
(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 Chamois Shirt, Traditional Fit, Plaid
L.L.Bean Men's Chamois Shirt, Traditional Fit, Plaid
A warm orange plaid flannel shirt-jacket, brushed for softness and reinforced with durable double-stitched seams.
(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 flannel shirt expertly brushed for softness, warmth and durability, with rugged double-stitched seams.
(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 blue plaid shirt crafted from premium 100% cotton Portuguese flannel with a button-down collar.
(6,433)
$59.95 $59.95
SALE
What customers like:
Quality construction
Perfect fit
Softness
Warmth
Vibrant colors
$59.95 $59.95
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit
A blue 100% cotton canvas shirt with a broken-in feel, durable stitching, and practical button-flap pockets.
(5,386)
$69.95 $58.99
SALE
What customers like:
Versatile for seasons
High quality
Durable construction
Great color options
Comfortable fit
$69.95 $58.99
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 checked 100% cotton poplin shirt with wrinkle-free, moisture-wicking performance and a button-down collar.
(4,814)
$69.95 $69.95
SALE
What customers like:
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
$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 purple plaid shirt combining brushed cotton flannel with 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 Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit, Short-Sleeve, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit, Short-Sleeve, Check
A blue checked cotton button-down shirt with wrinkle-free, moisture-wicking fabric, short sleeves, and a buttoned collar.
(2,628)
$59.95 $59.95
SALE
$59.95 $59.95
SALE
Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth
A gray shearling-lined cotton flannel shirt with a button-down collar resisting shrinking, wrinkling and pilling.
(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 Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
A blue cotton button-down shirt with wrinkle-free, non-iron pinpoint oxford fabric and a relaxed traditional fit.
(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 blue, wrinkle-free cotton Oxford shirt with university stripes, traditional fit, shirttail hem and double-needle stitching.
(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 wrinkle-free, high-thread-count cotton, with an ultrasmooth finish and durable tailoring.
(2,091)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Comfort
Durability
$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-fitting 100% cotton Portuguese flannel shirt featuring authentic yarn-dyed Scottish tartans and button-down styling.
(1,791)
$59.95 $59.95
SALE
What customers like:
Attractive colors and patterns
Warm and cozy
Soft and comfortable fabric
Flattering slim fit
High quality construction
$59.95 $59.95
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
A prewashed orange cotton canvas shirt with rugged stitching, button-flap pockets, and a relaxed traditional fit.
(1,629)
$59.95 $50.99
SALE
What customers like:
Perfect fit
Durable and sturdy
Versatile style
Comfortable to wear
Soft fabric
$59.95 $50.99
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 blue cotton check shirt with wrinkle-free performance, moisture-wicking TrueCool® fabric and a button-down collar.
(1,619)
$69.95 $69.95
SALE
What customers like:
Flattering fit
Good quality
Wrinkle-free
Versatile style
Comfortable
$69.95 $69.95
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 brown plaid flannel shirt made from brushed cotton, with a slim fit and broken-in softness.
(1,273)
$89 $75.99
SALE
$89 $75.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
A midweight gray cotton flannel shirt with brushed softness, yarn-dyed plaid, durable stitching, and two button-close chest pockets.
(531)
$79.95 $79.95
SALE
What customers like:
Great fit
High-quality material
Well-built
Very comfortable
Excellent return policy
$79.95 $79.95
SALE
Men's Maine Guide Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Shirt with PrimaLoft
A warm, durable checked shirt crafted from an 85% wool and 15% nylon blend with PrimaLoft insulation.
(386)
$190 $190
SALE
What customers like:
Great fit
Excellent quality
Warmth
Durable
Comfortable
$190 $190
SALE
Men's Comfort Stretch® Oxford Shirt, Traditional Fit
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Traditional Fit
A red cotton-blend oxford shirt with stretch, moisture-wicking performance, and an easy untucked design.
(290)
$74.95 $54.99
SALE
What customers like:
Looks good untucked
Versatile style
Available in tall sizes
High-quality fabric
Comfortable fit
$74.95 $54.99
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 cotton-blend shirt with stretch, moisture-wicking comfort, and a shorter untucked-friendly hem.
(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 blue plaid shirt in stretchy recycled synthetic-nylon fabric with UPF 50+ sun 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 Lightweight Wool Field Shirt, Plaid
L.L.Bean Men's Maine Guide Lightweight Wool Field Shirt, Plaid
A red plaid wool-blend shirt offering durable warmth, odor resistance, snap cuffs, and chest pockets.
(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 orange cotton-acrylic hunting shirt with articulated bi-swing, reinforced forearms, and low-profile pockets.
(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 Winter Button Down Shirts

Men's winter button down shirts have a familiar place in a thoughtfully chosen wardrobe: classic enough to return to year after year, with plenty of room for individual style. The appeal begins with a straightforward design—a collar, a buttoned front and a shape that can look relaxed or more put together depending on the rest of the outfit. In everyday shopping, “button down” often refers to the front closure, while a button-down collar specifically has collar points that fasten to the shirt. That distinction can matter to someone who prefers a particular neckline or likes a consistent look across a shirt collection. Beyond those basic details, choosing a winter shirt is largely about the character it brings to clothes already worn and enjoyed. A preference for checks, stripes or solid colors offers a useful starting point, without requiring a completely different approach to getting dressed. Someone drawn to larger patterns may appreciate the way a shirt becomes the main visual element of an outfit; someone who favors understated clothing may prefer a quieter design that lets other pieces stand out. Color combinations matter as much as individual colors. A shirt that relates to the trousers, sweaters and jackets already in a closet is often easier to picture as part of a complete outfit. Winter dressing also gives collars, cuffs and shirt hems a distinct visual role, since they may be the portions visible alongside other clothing. A small check at the neckline creates a different impression from a broad stripe or a solid collar. These are modest details, but they help explain why two shirts with the same basic shape can feel quite different in a wardrobe. The most satisfying choice usually reflects an established sense of style, whether that means a familiar pattern, a simpler color combination or a slightly different take on a favorite shirt.

Fit gives those design choices their shape. A size label is only one part of the picture; the way a shirt sits across the shoulders, through the chest and around the waist determines its overall outline. Individual size charts and fit descriptions provide more useful context than assuming that every shirt with the same marked size will have the same proportions. A favorite shirt already in the closet can serve as a practical reference when comparing measurements, especially if its sleeve length and body length feel right. Shoulder placement, collar circumference and the position of the cuffs are worth considering together rather than as separate details. A shirt may have the preferred amount of room through the body yet still have sleeves that fall differently than expected. Hem length also changes the look: a longer line and a shorter line create different proportions against the same trousers. For anyone who alternates between a tucked and untucked appearance, the shape of the hem deserves a closer look in the product images. Personal preference remains important throughout. Some men favor a closer outline, while others prefer a more generous silhouette; neither choice needs to be treated as the default. Fabric composition and care information are additional points of comparison best considered at the individual shirt level. Those details establish what a particular shirt is made from and how it should be washed, dried or otherwise cared for. A familiar laundry routine can be a useful part of the decision, especially for someone who prefers consistent care requirements across a wardrobe. Following the directions on the garment label takes precedence over a general habit used for other shirts. Measurements, fabric details and care instructions may be less immediately noticeable than color or pattern, but they provide the practical information behind a considered purchase. Taken together, they make it easier to choose with a clear understanding of the shirt rather than relying on its photograph alone.

A winter button down shirt can also bring variety to an existing wardrobe without changing its overall direction. Repeating a color already found in a sweater or pair of trousers creates a visual connection, while introducing a contrasting pattern changes the balance of the outfit. There is no need for every element to match exactly. A small-scale pattern beside a larger, simpler area of color can look intentional without feeling overly coordinated. Similarly, the relationship between the collar and the neckline of another garment can make a familiar combination feel different. These styling details are personal rather than prescriptive: the aim is a shirt that feels like it belongs with the clothes its wearer already chooses. For shoppers considering related styles, men's outdoor button down shirts offer another collection to explore alongside winter selections. A broader comparison can help clarify preferences in appearance, fit and individual product details without making the decision more complicated than it needs to be. The same thoughtful approach applies when choosing a shirt as a gift. A partner, father, brother or friend may have clear preferences that are easy to recognize in the shirts he wears most often: a particular collar shape, a recurring pattern size, a consistent color family or a preferred silhouette. Those familiar choices are generally more useful clues than selecting something entirely unlike the rest of his wardrobe. Confirming the size and, when possible, comparing the fit description with an existing favorite adds another helpful reference point. A gift can still feel distinctive through a different pattern or color combination while staying close to the recipient's personal taste. Whether chosen for someone else or for an existing winter wardrobe, a button down shirt is most appealing when its details make sense together. A considered fit, a welcome design and clearly understood care requirements give the selection a practical foundation, while timeless style leaves room for the wearer to make it his own.
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