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Men's Relaxed Fit Shirts

Find men's relaxed fit shirts with a roomier cut for a less fitted look. Browse the selection for styles that suit your wardrobe, and check each shirt’s size and fit details to help you choose the fit you prefer.

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Men's Carefree Unshrinkable Tee, Traditional Fit, Short-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Short-Sleeve
A soft brown cotton tee with a traditional relaxed fit, resisting shrinkage, wrinkles, fading and pilling.
(12,867)
$26.95 $26.95
SALE
$26.95 $26.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
A gray cotton long-sleeve tee with a relaxed fit that resists shrinking, wrinkles, fading and pilling.
(10,664)
$36.95 $36.95
SALE
What customers like:
Durable and well-made
High quality fabric
Variety of colors
Maintains shape and color
Comfortable fit
$36.95 $36.95
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 flannel shirt in soft 100% cotton, resisting shrinkage, fading, wrinkles and pilling.
(8,393)
$79.95 $79.95
SALE
What customers like:
Great quality
Warm and cozy
Excellent fit
Comfortable
Superior softness
$79.95 $79.95
SALE
Men's Chamois Shirt, Traditional Fit
L.L.Bean Men's Chamois Shirt, Traditional Fit
A green, heavyweight chamois flannel shirt, brushed for softness with rugged double-stitched seams and layering room.
(7,136)
$79.95 $79.95
SALE
What customers like:
Nice colors
Great quality
Warmth
Versatile use
Comfortable fit
$79.95 $79.95
SALE
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
L.L.Bean Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
A soft blue cotton pocket tee that resists shrinking, wrinkles, fading, and pilling for everyday comfort.
(7,068)
$26.95 $26.95
SALE
What customers like:
No shrinkage
High quality material
Durable construction
Great color options
Comfortable fit
$26.95 $26.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
A blue cotton henley with relaxed fit that resists shrinking, wrinkles, fading and pilling.
(6,468)
$44.95 $44.95
SALE
What customers like:
Great fit
High quality
Versatile
Comfortable
Soft fabric
$44.95 $44.95
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 green checked cotton shirt with wrinkle-free, moisture-wicking fabric, button-down collar and traditional relaxed fit.
(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 Unshrinkable Mini-Waffle Henley, Traditional Fit, Long-Sleeve
L.L.Bean Men's Unshrinkable Mini-Waffle Henley, Traditional Fit, Long-Sleeve
A red cotton thermal shirt with a three-button henley neckline that resists shrinking, fading and pilling.
(4,807)
$69.95 $69.95
SALE
What customers like:
High quality
True to size
Comfortable
Warm
Good value
$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 Classic Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
A white, wrinkle-free 100% cotton Oxford shirt with traditional fit and classic button-down styling.
(3,567)
$64.95 $64.95
SALE
What customers like:
High quality
Wrinkle-free
Versatile style
Durable
Comfortable fit
$64.95 $64.95
SALE
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit, Long-Sleeve
A soft white cotton pocket tee with long sleeves that resists shrinking, wrinkles, fading, and pilling.
(3,527)
$36.95 $36.95
SALE
What customers like:
High quality
Convenient pocket
Great color
Durable material
Comfortable fit
$36.95 $36.95
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
A gray cotton henley shirt resists shrinking, wrinkles, fading and pilling for dependable everyday comfort.
(3,027)
$32.95 $32.95
SALE
What customers like:
Easy care
Perfect fit
Durable fabric
Versatile design
True to size
$32.95 $32.95
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 cotton check shirt with wrinkle-free, moisture-wicking performance, a buttoned collar, and relaxed traditional fit.
(2,628)
$59.95 $59.95
SALE
What customers like:
Generous fit
High quality
Wrinkle-free
Easy to wear
Comfortable fabric
$59.95 $59.95
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 pinpoint oxford shirt with a wrinkle-free finish, traditional fit, and durable single-needle tailoring.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Versatile
Comfortable
$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, durable construction and a shirttail hem.
(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 Tropics Shirt, Traditional Fit, Print
L.L.Bean Men's Tropics Shirt, Traditional Fit, Print
A soft, breathable green cotton shirt with a tropical print, spread collar and relaxed traditional fit.
(2,027)
$54.95 $54.95
SALE
What customers like:
Great color and pattern
Durable quality
Versatile style
Cool and lightweight
Comfortable fit
$54.95 $54.95
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
A tan cotton canvas shirt with short sleeves, button-flap pockets and a relaxed, broken-in feel.
(1,629)
$59.95 $59.95
SALE
$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 green checked cotton sport shirt with moisture-wicking, wrinkle-free performance and a comfortable slightly fitted design.
(1,619)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve
A green cotton-blend shirt with stretch, moisture-wicking comfort, long sleeves and a shorter untucked-friendly hem.
(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 Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve, Print
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve, Print
A red cotton-blend shirt with stretch, moisture-wicking comfort, and a versatile untucked hem.
(1,159)
$74.95 $54.99
SALE
What customers like:
Soft and stretchy fabric
True to size fit
Versatile style
Comfortable material
High quality construction
$74.95 $54.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve, Plaid
A pink plaid short-sleeve shirt in moisture-wicking stretch cotton blend, designed for breathable comfort and movement.
(845)
$59.95 $39.99
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Stylish design
Durable
$59.95 $39.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
A gray midweight cotton flannel with yarn-dyed plaid, brushed softness, durable stitching and buttoned 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 Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve, Stripe
A red striped cotton-blend shirt with stretch, moisture-wicking comfort, and a shorter untucked hem.
(294)
$59.95 $39.99
SALE
$59.95 $39.99
SALE

Men's Relaxed Fit Shirts

Men’s relaxed fit shirts offer a roomier silhouette for anyone who prefers a little space between a shirt and the body. Rather than following the torso closely, a relaxed fit generally allows more room through the chest and waist, though the exact proportions depend on the individual design. That distinction makes fit worth considering separately from size: a relaxed shirt in a familiar size is not necessarily the same as a larger shirt in a closer cut. Sizing up can also change the shoulder position, sleeve length and overall length, while choosing a relaxed fit starts with a different shape. The appeal is a shirt that looks intentionally easygoing, with proportions that suit the person wearing it. For men who prefer a less fitted look, that extra room can be an important part of personal style, whether the preference is for a straight silhouette or a shirt that falls more loosely around the middle. A favorite shirt already in the closet provides a useful point of comparison. Its chest width, shoulder placement and hem length can help put a size chart into perspective more clearly than a size label alone. The most helpful product details distinguish the fit from the styling, so a collar shape or pattern does not have to stand in for information about the cut. Relaxed fit also does not have to mean an exaggerated, oversized appearance. The visual balance comes from how the shoulders, sleeves and body work together. A shoulder seam that sits where expected and a hem that ends at a preferred length can make a generous cut look considered rather than simply large. Across men’s shirts, these proportions help define the difference between a shape that happens to fit and one that feels like a natural expression of the wearer’s taste.

The character of a relaxed fit shirt comes from more than its outline. Color, pattern, collar shape, pocket placement and the line of the hem all influence the finished look, giving shirts with a similar fit distinct personalities. A small-scale pattern creates a different impression from a broad stripe, just as a simple front looks different from one with more visible detailing. Preferences in these details are often closely tied to the clothes someone already enjoys wearing. A wardrobe built around understated colors may call for another quiet, familiar shade, while someone who enjoys pattern may see a shirt as the central visual element of an outfit. Neither approach requires a close-fitting silhouette to look put together. The relationship between the shirt and the rest of the outfit matters more than following a single rule about how relaxed clothing should look. A generous shirt above a straighter trouser shape creates one set of proportions; a fuller shape throughout creates another. Hem length deserves particular attention when an untucked look is the preference, since a small difference in where the shirt ends can noticeably change the overall balance. For a tucked look, the amount of fabric around the waist becomes a different consideration. Photographs can offer a sense of these details, but measurements and fit descriptions provide important context that an image cannot always convey. Sleeve length is another separate choice, not a substitute for understanding the fit through the body. Personal preferences about cuffs, necklines and visible buttons can be just as meaningful as the amount of room through the chest. For a related collection, explore Mens Walking Shirts. Keeping the focus on each shirt’s own description makes it easier to distinguish the collection’s theme from the particular shape, details and specifications of an individual design.

Choosing among men’s relaxed fit shirts also involves the less visible details that make a purchase feel well considered. Fabric composition and care instructions belong to the individual shirt, not to the relaxed fit designation. Two shirts with a similar outline can have different fabric specifications and laundering requirements, so those details deserve their own attention rather than assumptions based on appearance. The care label is the appropriate reference for washing, drying and any ironing instructions. For someone who has a firmly established laundry routine, knowing those requirements before choosing a shirt can be as useful as knowing its measurements. Quality is worth considering with the same attention to specifics: clear construction information and detailed photographs offer more substance than relying on a fit name to say anything about how a garment is made. A relaxed cut describes shape; it does not, by itself, establish fabric weight, care needs or longevity. That separation helps keep the choice centered on what matters to the wearer. For some, the deciding detail is room through the waist without an unexpectedly long hem. For others, it is a familiar collar, a preferred sleeve length or a pattern that fits naturally alongside existing favorites. Shirts can also be thoughtful gifts when those preferences are known. A partner, parent, sibling or friend who consistently chooses a roomier cut may appreciate a selection grounded in that preference rather than a guess about what they should wear. A known size is a useful starting point, but the recipient’s preferred fit and the measurements of a shirt they like give the choice more context. Familiar colors and understated details can reflect close attention to personal taste without requiring a completely different style. Ultimately, the lasting appeal of a relaxed fit is its straightforward point of view: a more generous shape, chosen deliberately. Combined with careful attention to proportions and individual product details, that approach leaves room for personal expression while keeping the shirt itself an uncomplicated part of getting dressed.
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