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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.

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Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
A wrinkle-free, 100% cotton poplin shirt in nautical blue check with moisture-wicking TrueCool® fabric.
(4,814)
$69.95 $69.95
SALE
What customers like:
High quality
Wrinkle-free
Lightweight
Good fit
Comfortable
$69.95 $69.95
SALE
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
A wrinkle-free, 100% cotton oxford shirt in French blue with a relaxed traditional fit.
(3,567)
$64.95 $64.95
SALE
What customers like:
High quality
Wrinkle-free
Durable
Stylish appearance
Comfortable fit
$64.95 $64.95
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 deep green, wrinkle-free cotton shirt with moisture-wicking TrueCool® fabric and a relaxed traditional fit.
(2,628)
$59.95 $49.99
SALE
What customers like:
Vivid colors
Wrinkle-free
Great quality
Durable material
Comfortable fit
$59.95 $49.99
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 wrinkle-free white cotton shirt offering a relaxed traditional fit and ultrasmooth finish.
(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 wrinkle-free, 100% cotton oxford shirt with a traditional fit and stylish French blue university stripes.
(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 wrinkle-free blue tattersall shirt in 100% cotton offers a nearly custom, 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 Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
A nautical blue, wrinkle-free cotton shirt with moisture-wicking TrueCool® fabric and a slightly fitted check pattern.
(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 Stretch Poplin Shirt, Short-Sleeve, Slim Fit
L.L.Bean Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
A blue slim-fit short-sleeve shirt made from a soft cotton blend with a button-down collar.
(0)
$69.95 $34.99
SALE
$69.95 $34.99
SALE
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
L.L.Bean Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
A slim-fit purple oxford shirt crafted from 100% Pima cotton for exceptional softness and comfort.
(0)
$89 $74.99
SALE
$89 $74.99
SALE
Men's Signature Donegal Woven Shirt, Long-Sleeve
L.L.Bean Men's Signature Donegal Woven Shirt, Long-Sleeve
A rugged brown twill flannel shirt featuring Donegal flecks and a slim, tailored fit.
(0)
$79.95 $59.99
SALE
$79.95 $59.99
SALE
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
L.L.Bean Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
A slim-fit, walnut-colored stretch poplin shirt made from a soft cotton blend with a button-down collar.
(0)
$79 $38.99
SALE
$79 $38.99
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
A lightweight, deep blue heather cotton shirt with a relaxed fit and brushed for extra softness.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Men's Signature Wharfside Linen Blend Shirt
L.L.Bean Men's Signature Wharfside Linen Blend Shirt
A breathable tan linen-cotton blend shirt with a slim fit, button-down collar, and chest pocket.
(0)
$74.95 $54.99
SALE
$74.95 $54.99
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
A brown cotton-blend chambray shirt with moisture-wicking, quick-drying stretch and a slightly fitted untucked fit.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Madras Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Madras Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
A lightweight blue cotton madras shirt with vibrant plaid, designed for untucked comfort and breathability.
(0)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
L.L.Bean Men's Scotch Plaid Flannel Shirt, Slightly Fitted
A slightly fitted flannel shirt in authentic Scottish tartans, crafted from high-quality Portuguese cotton.
(6,433)
$59.95 $49.99
SALE
What customers like:
High quality
Perfect fit
Softness
Warmth
Comfortable
$59.95 $49.99
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit
A prewashed, 100% cotton canvas shirt in juniper with a relaxed fit and durable double-needle stitching.
(5,386)
$69.95 $69.95
SALE
What customers like:
High quality
Durable
Comfortable
Good fit
Nice color
$69.95 $69.95
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 antique dress stewart tartan, made from high-quality Portuguese cotton.
(1,791)
$59.95 $44.99
SALE
What customers like:
Rich colors
Perfect fit
Soft and comfortable
Stylish design
High-quality cotton
$59.95 $44.99
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit Short-Sleeve
A soft, prewashed orange cotton canvas shirt with a relaxed fit and durable double-needle stitching.
(1,629)
$59.95 $50.99
SALE
What customers like:
Versatile and stylish
Perfect fit and true to size
Durable and sturdy
Soft and high-quality fabric
Comfortable to wear
$59.95 $50.99
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 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 and moisture-wicking, perfect for untucked 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 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 soft brushed finish and durable triple-needle stitching.
(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 PrimaLoft wool blend shirt with sturdy seams and generous cuffs, ideal for layering.
(386)
$190 $190
SALE
What customers like:
Great fit
Durable construction
Excellent quality
Warm and comfortable
Stylish appearance
$190 $190
SALE
Men's Maine Guide Shirt
L.L.Bean Men's Maine Guide Shirt
A durable, 85% wool, 15% nylon plaid shirt in cobalt or black, perfect for layering.
(352)
$170 $170
SALE
What customers like:
Great fit
High quality
Good quality
Cushioning
Warm
$170 $170
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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