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Relaxed Winter Shirts

Find relaxed winter shirts with an easygoing fit and timeless style to complement your winter wardrobe. Explore the selection and check each shirt’s fit, sizing and care details to help choose the right one for you.

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Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley
L.L.Bean Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley
A classic charcoal Henley with a wool blend outer layer and soft cotton inner layer for warmth.
(6,147)
$79.95 $79.95
SALE
What customers like:
Quality construction
Perfect fit
Warmth
Comfortable
Versatility
$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 deep green, 100% cotton, wrinkle-free sport shirt with moisture-wicking TrueCool® fabric and a relaxed fit.
(4,814)
$69.95 $58.99
SALE
What customers like:
High quality
Wrinkle-free
Lightweight
Good fit
Comfortable
$69.95 $58.99
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 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 Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
L.L.Bean Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
A blue striped chambray shirt in a breathable cotton blend with stretch and a modern untucked hem.
(267)
$74.95 $54.99
SALE
What customers like:
Modern untucked hem
Easy to care for
Stylish design
Great fabric quality
Comfortable fit
$74.95 $54.99
SALE
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit
A light cobalt, slightly fitted oxford shirt with moisture-wicking cotton blend and stretch for comfort.
(251)
$74.95 $54.99
SALE
What customers like:
High material quality
Well-made
Cute print
Great appearance
Comfortable
$74.95 $54.99
SALE
Men's Maine Guide Zip-Front Jac-Shirt, Plaid
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt, Plaid
A rugged wool/nylon jac-shirt in green and black plaid, perfect for layering and outdoor activities.
(202)
$200 $200
SALE
What customers like:
Great fit
High quality
Warmth
Durable
Comfortable fabric
$200 $200
SALE
Men's Tropicwear Shirt, Plaid Long-Sleeve
L.L.Bean Men's Tropicwear Shirt, Plaid Long-Sleeve
A blue plaid long-sleeve shirt with UPF 50+ protection and built-in stretch for comfort.
(159)
$79.95 $59.99
SALE
What customers like:
Effective sun protection
High quality
Attractive appearance
Cool and comfortable fabric
Good fit
$79.95 $59.99
SALE
Men's Maine Guide Zip-Front Jac-Shirt
L.L.Bean Men's Maine Guide Zip-Front Jac-Shirt
A versatile wool/nylon jac-shirt with a relaxed fit, ideal for layering or wearing solo year-round.
(126)
$190 $190
SALE
$190 $190
SALE
Women's Maine Guide Zip Front Jac-Shirt with PrimaLoft
L.L.Bean Women's Maine Guide Zip Front Jac-Shirt with PrimaLoft
A loden wool blend jac-shirt with PrimaLoft insulation, featuring multiple pockets and a rugged brass zipper.
(28)
$250 $250
SALE
What customers like:
Great fit
High quality
Non-itchy material
Excellent warmth
$250 $250
SALE
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
A lightweight chambray shirt in a cotton blend with moisture-wicking, quick-drying fabric and a slightly fitted untucked fit.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
SALE
Women's Whisperweight Flannel Shirt, Squareneck
L.L.Bean Women's Whisperweight Flannel Shirt, Squareneck
A superlight red cotton flannel shirt featuring a feminine squareneck and blousant sleeves with elastic cuffs.
(0)
$69.95 $39.99
SALE
$69.95 $39.99
SALE
Men's Sunwashed Twill Shirt, Slightly Fitted Untucked Fit
L.L.Bean Men's Sunwashed Twill Shirt, Slightly Fitted Untucked Fit
A lightweight blue cotton twill shirt with a button-down collar, subtle texture, and untucked fit.
(0)
$69.95 $59.99
SALE
$69.95 $59.99
SALE
Women's Whisperweight Flannel Shirt, Button-Down
L.L.Bean Women's Whisperweight Flannel Shirt, Button-Down
A superlight tan flannel button-down shirt offering year-round comfort with a relaxed, easy fit.
(0)
$69.95 $51.99
SALE
$69.95 $51.99
SALE
Men's Sunwashed Textured Shirt, Slightly Fitted, Plaid
L.L.Bean Men's Sunwashed Textured Shirt, Slightly Fitted, Plaid
A lightweight brown cotton blend shirt with a subtle textured finish and a relaxed, untucked fit.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
A brown plaid cotton-blend shirt featuring quick-drying, moisture-wicking stretch fabric and a relaxed untucked fit.
(0)
$74.95 $74.95
SALE
$74.95 $74.95
SALE
Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit
L.L.Bean Men's 1912 Field Flannel Shirt, Lined, Slightly Fitted Untucked Fit
A brown cotton flannel shirt with a soft jersey-knit lining, designed for comfort and untucked style.
(0)
$99.95 $64.99
SALE
$99.95 $64.99
SALE
Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Traditional Untucked Fit
A lightweight gray cotton twill shirt with a soft brushed finish and a relaxed untucked fit.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Print
L.L.Bean Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Print
A blue cotton-blend shirt featuring quick-drying, moisture-wicking stretch fabric and a relaxed untucked fit.
(0)
$79.95 $59.99
SALE
$79.95 $59.99
SALE

Relaxed Winter Shirts

Relaxed Winter Shirts bring an easygoing feel to a winter wardrobe, with a look that leaves room for personal style. There’s something satisfying about finding a shirt that feels like you: a familiar color, a pattern you enjoy, a shape that looks just as natural tucked in as it does left loose. As you browse, consider what you already reach for most often. Muted shades can sit comfortably alongside the rest of your wardrobe, while a more noticeable pattern can give a simple outfit a little character. Neither approach needs much fuss. A shirt that complements your favorite pants and the pieces you already own is often a more welcome addition than one that calls for an entirely different outfit. Start with your own preferences rather than a look you feel you ought to wear.

When choosing a relaxed shirt, pay attention to the proportions as well as the size on the label. A relaxed silhouette and a larger size aren’t necessarily the same thing, so check each item’s fit description and measurements before deciding. Shoulder placement, sleeve length and the length of the shirt can all affect whether the overall look feels right to you. One useful starting point is a shirt you already love: lay it flat, take its measurements and compare them with the available sizing information. If you usually wear shirts untucked, look closely at where the hem falls; if you prefer a tuck, consider how that length works with your usual pants. Product photos can help you picture the shape, but the individual details offer a better basis for comparison. Check care instructions, too, so your choice fits the routine you’re comfortable keeping.

Relaxed Winter Shirts can also make a thoughtful gift for someone who appreciates an unhurried, understated style. The best clues are often already in their closet: the colors they choose repeatedly, whether they favor plain shirts or patterns, and how loosely they like their clothes to fit. Think of the shirt they reach for without hesitation, the one that seems entirely their own, rather than trying to reinvent their style. If you’re unsure about sizing, a current favorite offers a more useful reference than a guess based on appearance. For your own wardrobe, take the same thoughtful approach. Picture the shirt beside the pants you wear most and beneath the jacket hanging by the door. Choosing familiar proportions with a small change in color or pattern can make an addition feel fresh while still feeling like you.

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