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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.

Men's Carefree Unshrinkable Tee, Traditional Fit, Short-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Short-Sleeve
A green cotton jersey-knit T-shirt with a relaxed traditional fit and durable, shrink-resistant construction.
(12,867)
$26.95 $26.95
SALE
What customers like:
Great fit
High quality
Durable
Comfortable
Soft fabric
$26.95 $26.95
SALE
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
L.L.Bean Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
A blue cotton pocket tee that resists shrinking, wrinkles, fading and pilling for lasting 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 Sunwashed Canvas Shirt, Traditional Fit
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit
A green cotton canvas shirt with a broken-in feel, relaxed fit, button-flap pockets and double-needle stitching.
(5,386)
$69.95 $69.95
SALE
What customers like:
High quality
Durable construction
Versatile for spring and fall
Great color options
Comfortable fit
$69.95 $69.95
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 a relaxed traditional fit that resists shrinking, wrinkles, fading and pilling.
(6,468)
$44.95 $44.95
SALE
What customers like:
Perfect fit
No shrinkage
Durable fabric
True to size
Soft and comfy
$44.95 $44.95
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 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 short-sleeve cotton sport shirt in a blue check pattern with wrinkle-free, moisture-wicking fabric.
(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 Carefree Unshrinkable Tee, Traditional Fit, Henley
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
A gray cotton henley tee with a relaxed fit that resists shrinking, wrinkles, fading and pilling.
(3,027)
$32.95 $32.95
SALE
What customers like:
Easy care
Perfect fit
Stylish design
Durable fabric
True to size
$32.95 $32.95
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 button-down shirt with wrinkle-free fabric, university stripes, and 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 Tropics Shirt, Traditional Fit, Print
L.L.Bean Men's Tropics Shirt, Traditional Fit, Print
A printed green cotton shirt, breathable and lightly peached, with relaxed traditional fit and side vents.
(2,027)
$54.95 $44.99
SALE
What customers like:
Great color and pattern
Durable quality
Versatile style
Cool and lightweight
Comfortable fit
$54.95 $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 tan cotton short-sleeve button-down shirt with a relaxed fit, patch pockets and durable double-needle stitching.
(1,629)
$59.95 $59.95
SALE
What customers like:
Perfect fit
Durable and sturdy
Versatile style
Comfortable to wear
Soft fabric
$59.95 $59.95
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 long-sleeve chambray shirt in moisture-wicking cotton blend with stretch and a relaxed traditional fit.
(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 brown chambray shirt in moisture-wicking stretch cotton blend, with long sleeves and a relaxed fit.
(1,159)
$74.95 $54.99
SALE
$74.95 $54.99
SALE
Men's Katahdin Performance Flannel Shirt
L.L.Bean Men's Katahdin Performance Flannel Shirt
A blue flannel shirt in wool-blend fabric with quick-drying, water-repellent performance and reinforced elbows.
(0)
$99.95 $74.99
SALE
$99.95 $74.99
SALE
Men's Riverton Ripstop Shirt, Traditional Fit, Long-Sleeve
L.L.Bean Men's Riverton Ripstop Shirt, Traditional Fit, Long-Sleeve
A lightweight tan cotton-blend ripstop shirt with stretch and a relaxed fit for comfortable movement.
(0)
$79.95 $54.99
SALE
$79.95 $54.99
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 men's short-sleeve chambray shirt in moisture-wicking stretch cotton blend, relaxed traditional fit.
(294)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve, Print
L.L.Bean Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve, Print
A blue short-sleeve button-front shirt in textured TENCEL™ lyocell blend with a relaxed fit and print.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
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 performance, long sleeves, and a shorter untucked hem.
(267)
$74.95 $54.99
SALE
What customers like:
Easy to care for
Great fabric quality
Breathable material
Stylish appearance
Comfortable fit
$74.95 $54.99
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Fit, Plaid
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Fit, Plaid
A soft tan plaid cotton shirt with brushed twill, button-down collar, and relaxed traditional fit.
(0)
$69.95 $39.99
SALE
$69.95 $39.99
SALE
Men's Riverton Ripstop Shirt, Traditional Fit, Short-Sleeve
L.L.Bean Men's Riverton Ripstop Shirt, Traditional Fit, Short-Sleeve
A brown short-sleeve shirt in durable cotton-blend micro ripstop fabric, with stretch and a relaxed fit.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
L.L.Bean Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
A green long-sleeve cotton T-shirt with a relaxed fit that resists shrinking, wrinkles, fading, and pilling.
(10,664)
$36.95 $36.95
SALE
What customers like:
Well-made
Durable
Comfortable
Good fit
Soft fabric
$36.95 $36.95
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Fit
A gray cotton twill shirt with brushed softness, button-down collar, and relaxed traditional fit.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve
L.L.Bean Men's Sunwashed Ultrasoft Button-Front Shirt, Short-Sleeve
A gray short-sleeve shirt in textured TENCEL™ lyocell blend, with a relaxed fit and chest pocket.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
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 with cozy sheepskin lining and brushed 100% cotton comfort.
(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 men's flannel shirt in heavyweight brushed Portuguese cotton with durable stitching and angled pockets.
(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 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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