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Tailored Men's Shirts

Find tailored men's shirts for a clean, polished look, with timeless style at the heart of the selection. Compare individual shirts’ fit descriptions and sizing details to find the shape and proportions that work best for you.

Men's Signature Premium Pima Cotton Oxford Shirt, Slim Fit
L.L.Bean Men's Signature Premium Pima Cotton Oxford Shirt, Slim Fit
A purple Oxford shirt in 100% Pima cotton, tailored slim with button-down collar and untucked hem.
(0)
$89 $59.99
SALE
$89 $59.99
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 white cotton oxford shirt with a wrinkle-free finish, traditional fit, and durable, expertly tailored construction.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Professional look
Versatile
$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 cotton Oxford shirt with university stripes, wrinkle-free fabric, traditional fit, and meticulous reinforced 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 cotton tattersall shirt with an ultrasmooth, wrinkle-free pinpoint oxford weave and traditional fit.
(2,091)
$79.95 $79.95
SALE
What customers like:
High quality
Wrinkle-free
Easy to care for
Durable
Comfortable fit
$79.95 $79.95
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Slim Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Slim Fit, Check
A green cotton sport shirt with wrinkle-free, moisture-wicking fabric, button-down collar and slim fit.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
SALE
Men's Signature Donegal Woven Shirt, Slim Fit
L.L.Bean Men's Signature Donegal Woven Shirt, Slim Fit
A white cotton twill flannel shirt with Donegal flecks, button-down collar, chest pocket and slim fit.
(0)
$79.95 $54.99
SALE
$79.95 $54.99
SALE
Men's Signature Northwoods Twill Shirt, Slim Fit
L.L.Bean Men's Signature Northwoods Twill Shirt, Slim Fit
A black men's cotton twill shirt with a slim fit, subtle texture, and button-closure front pockets.
(0)
$89 $75.99
SALE
$89 $75.99
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 cotton flannel shirt with angled flap pockets and brushed, garment-washed softness.
(1,273)
$89 $75.99
SALE
$89 $75.99
SALE
Men's Signature Brushed Herringbone Shirt, Slim Fit
L.L.Bean Men's Signature Brushed Herringbone Shirt, Slim Fit
A gray men's button-down shirt in brushed cotton twill with herringbone texture and slim fit.
(0)
$89.95 $89.95
SALE
$89.95 $89.95
SALE
Men's Signature Northwoods Henley, Stripe
L.L.Bean Men's Signature Northwoods Henley, Stripe
A slim-fit tan striped cotton henley with supersoft jersey fabric, ribbed trim and contrast detailing.
(0)
$79 $66.99
SALE
$79 $66.99
SALE
Men's Signature Northwoods Henley, Slim Fit
L.L.Bean Men's Signature Northwoods Henley, Slim Fit
A gray cotton henley with a slim fit, ribbed trim, tonal buttons and soft jersey-knit comfort.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Signature Wharfside Linen Blend Shirt, Slim Fit
L.L.Bean Men's Signature Wharfside Linen Blend Shirt, Slim Fit
A tan slim-fit button-down shirt in breathable linen-cotton blend, featuring a chest pocket and button-down collar.
(0)
$74.95 $54.99
SALE
$74.95 $54.99
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 white chamois flannel shirt with brushed, garment-washed cotton, angled flap pockets and shirttail hem.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
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 green cotton check sport shirt with wrinkle-free, moisture-wicking fabric and a button-down collar.
(1,619)
$69.95 $69.95
SALE
What customers like:
Versatile color
Flattering design
High-quality fabric
Wrinkle-free performance
Comfortable fit
$69.95 $69.95
SALE
Men's Comfort Stretch® Chambray Shirt, Slightly Fitted, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Slightly Fitted, Short-Sleeve, Plaid
A blue plaid short-sleeve chambray shirt in moisture-wicking stretch cotton blend with a slightly fitted silhouette.
(0)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Maine Guide Shirt with PrimaLoft
L.L.Bean Men's Maine Guide Shirt with PrimaLoft
A warm plaid wool-blend shirt with PrimaLoft insulation, sturdy seams and generous cuffs for easy layering.
(386)
$190 $190
SALE
What customers like:
Great fit
Durable construction
Excellent quality
Warm and comfortable
Stylish appearance
$190 $190
SALE
Men's Signature Stretch Poplin Shirt, Slim Fit, Short-Sleeve
L.L.Bean Men's Signature Stretch Poplin Shirt, Slim Fit, Short-Sleeve
A blue short-sleeve button-down shirt in soft stretch cotton poplin, cut slim for untucked comfort.
(0)
$69.95 $34.99
SALE
$69.95 $34.99
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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 stretch poplin shirt in cotton blend with long sleeves and an untucked hem.
(0)
$79 $29.99
SALE
$79 $29.99
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 cotton checked sport shirt with wrinkle-free, moisture-wicking fabric, short sleeves, and a traditional fit.
(2,628)
$59.95 $59.95
SALE
What customers like:
Wrinkle-free
Great color
Durable
Comfortable
Good fit
$59.95 $59.95
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Slightly Fitted, Short-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Slightly Fitted, Short-Sleeve
A blue short-sleeve chambray shirt in moisture-wicking, quick-drying cotton-blend stretch fabric with a slightly fitted cut.
(0)
$54.95 $54.95
SALE
$54.95 $54.95
SALE
Men's 1933 Chamois Cloth Shirt, Slim Fit
L.L.Bean Men's 1933 Chamois Cloth Shirt, Slim Fit
A slim-fitting black chamois flannel shirt with brushed, garment-washed softness and authentic angled flap pockets.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
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 blue checked cotton button-down shirt with wrinkle-free, moisture-wicking fabric and a chest pocket.
(4,814)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Fit
A blue cotton twill shirt with brushed softness, twisted jaspé texture, button-down collar, and chest pocket.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Men's Scotch Plaid Flannel Shirt, Slim Fit
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slim Fit
A blue men's flannel shirt in 100% Portuguese cotton, featuring authentic tartan and a button-down collar.
(1,791)
$59.95 $59.95
SALE
What customers like:
Rich colors and patterns
Perfect fit
Soft and comfortable
Warm and durable
High quality cotton
$59.95 $59.95
SALE

Tailored Men's Shirts

Tailored men’s shirts bring a more defined shape to a familiar wardrobe essential, with an emphasis on proportion rather than extra fullness. In ready-to-wear clothing, “tailored” generally describes the shirt’s cut; it does not necessarily mean the garment has been made to an individual’s measurements. That distinction matters when comparing shirts, since a tailored fit, a made-to-measure shirt, and a custom-made shirt represent different approaches to sizing. A ready-to-wear tailored shirt starts with an established size and silhouette, while made-to-measure and custom clothing involve individual measurements. The appeal of a tailored silhouette is its balanced appearance: a shoulder line that sits where it should, sleeves that look proportionate, and a body shape that follows the wearer without looking oversized. Tailored does not have to mean tight, and it is not a label reserved for one body type. The amount of shaping varies, so the fit description and size chart offer more useful information than the word alone. Two shirts with the same listed size may have different proportions through the chest, waist, or sleeves. For someone who finds a fuller cut too loose through the middle, those differences can be especially meaningful. For someone who prefers more room, a tailored shape deserves a closer look at the measurements before choosing a size. The strongest starting point is often a shirt already in the closet whose proportions feel right. Its shoulder width, chest measurement, sleeve length, and overall length provide a familiar reference for interpreting another shirt’s dimensions, provided the measurements are taken in the same way. Across tailored men’s shirts, the defining consideration is the relationship between the garment’s shape and the person wearing it—not simply choosing the narrowest cut. A well-considered silhouette looks intentional without making the shirt the center of attention, leaving room for individual taste in the details.

Much of a tailored shirt’s character comes from how its individual elements relate to one another. The collar frames the face, the front creates a clean visual line, and the cuffs finish the sleeves. A collar that looks modest on one person may appear more pronounced on another, just as the same sleeve length can sit differently depending on shoulder width. These small differences explain why the overall impression matters as much as a size label. In a fitting-room mirror, the useful details are often straightforward: where the shoulder seams fall, whether the buttoned front lies flat, and how much extra fabric gathers at the waist. Pulling across the chest or gaps between buttons can suggest that a shirt’s proportions are not the right match, even if the labeled size seems familiar. Excess fabric can point to a different mismatch rather than an automatic need to size down. Length is another part of the silhouette worth considering alongside width. A shirt’s hem changes the visual balance between the upper and lower body, and its appearance may differ depending on how the wearer prefers to style it. Looking at front, side, and back views helps put those proportions in context. Personal preferences matter here, too. Some men favor a closer line through the torso; others want a more subtle distinction from a fuller shirt. Neither preference requires an exaggerated shape. The aim is a shirt that looks like a natural part of the wearer’s wardrobe, not a departure from it. Fabric composition, construction details, and care directions are separate considerations, and the individual shirt description is the place to confirm them. A tailored-fit label does not identify the material or establish how a shirt should be washed, dried, or pressed. It also does not establish durability or any particular performance feature. Keeping those details separate makes comparisons clearer: silhouette describes shape, while the garment’s own information explains its composition and care requirements. That distinction helps give every detail its proper weight without asking one fit term to tell the whole story.

Choosing among tailored men’s shirts also involves recognizing the details that make a wardrobe feel personal. A familiar collar shape, a preferred cuff proportion, or a particular balance between shoulder width and waist shaping can matter more than a dramatic change in appearance. Men who have worn the same general shirt shape for years may appreciate a measured adjustment rather than an entirely different look. Others may already know that a more defined silhouette is their preference and simply want consistency when comparing options. In either case, the best reference is the wearer’s actual preferences, not an assumption about what a tailored shirt ought to look like. The same approach is helpful when considering a shirt as a gift. A partner, parent, adult son, or friend may have clear opinions about fit even if those preferences rarely come up in conversation. Knowing the recipient’s usual size is helpful, but knowing whether that person favors a shaped or fuller silhouette adds important context. A shirt they already enjoy wearing can offer clues about proportions without turning the gift into a guess based on appearance alone. Care preferences deserve similar attention. Before making a choice, checking the garment’s care label helps establish whether its requirements align with the recipient’s routine; the word “tailored” provides no shortcut to that information. For another way to explore shirts, browse Mens Occasion Shirts alongside this collection. Within a tailored-shirt wardrobe, a sense of continuity can come from repeating the proportions that feel familiar while allowing smaller visual details to vary. There is no need for every shirt to look identical, nor for every choice to introduce something entirely new. A thoughtful selection starts with a clear understanding of fit and leaves the rest to personal style. That is the enduring appeal of tailored men’s shirts: a recognizable essential viewed through the details of shape, proportion, and individual preference.

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