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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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Women's Scotch Plaid Flannel Shirt, Relaxed
L.L.Bean Women's Scotch Plaid Flannel Shirt, Relaxed
A blue plaid flannel shirt crafted from brushed 100% Portuguese cotton for exceptional softness and warmth.
(14,442)
$59.95 $59.95
SALE
What customers like:
High quality
Warmth
Softness
Classic style
Comfortable fit
$59.95 $59.95
SALE
Women's Comfort Corduroy Relaxed Shirt
L.L.Bean Women's Comfort Corduroy Relaxed Shirt
A plush brown cotton corduroy shirt with a relaxed fit, low-hip length and convenient front and side pockets.
(6,858)
$59.95 $29.99
SALE
What customers like:
High quality and durable construction
Versatile for layering or wearing as a jacket
Very comfortable fit
Soft and warm fabric
Practical with deep and multiple pockets
$59.95 $29.99
SALE
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 gray two-layer henley in a cotton-merino wool blend, designed to trap warmth and dry quickly.
(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 green cotton check shirt with wrinkle-free, moisture-wicking fabric, a button-down collar and relaxed traditional fit.
(4,814)
$69.95 $69.95
SALE
What customers like:
Perfect fit
Wrinkle-free
Durable
Comfortable
Beautiful colors
$69.95 $69.95
SALE
Women's Wrinkle-Free Pinpoint Oxford Shirt, Relaxed Fit Long-Sleeve Print
L.L.Bean Women's Wrinkle-Free Pinpoint Oxford Shirt, Relaxed Fit Long-Sleeve Print
A blue cotton shirt with a relaxed fit, long sleeves, playful print, and wrinkle-resistant comfort.
(2,754)
$79.95 $79.95
SALE
$79.95 $79.95
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 red checked cotton sport shirt with wrinkle-free performance, moisture-wicking comfort and a buttoned collar.
(2,628)
$59.95 $49.99
SALE
What customers like:
Great fit and true to size
Attractive colors and stylish appearance
Wrinkle-free and easy care
Comfortable and soft fabric
Durable and well constructed
$59.95 $49.99
SALE
Men's Tropics Shirt, Traditional Fit, Print
L.L.Bean Men's Tropics Shirt, Traditional Fit, Print
A soft, breathable blue cotton shirt with a tropical print, spread collar and straight hem for cool-weather comfort.
(2,027)
$54.95 $54.95
SALE
What customers like:
Cool and breathable
Durable quality
Versatile style
Attractive color and pattern
Comfortable fit
$54.95 $54.95
SALE
Women's Vacationland Seersucker Shirt, Long-Sleeve
L.L.Bean Women's Vacationland Seersucker Shirt, Long-Sleeve
A relaxed-fit white striped cotton seersucker shirt with chest pockets and slightly longer coverage.
(1,957)
$59.95 $39.99
SALE
What customers like:
Soft material
Lightweight
Versatile
Comfortable
Good fit
$59.95 $39.99
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 red checked, wrinkle-free cotton poplin shirt with moisture-wicking TrueCool® fabric and a button-down collar.
(1,619)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Short-Sleeve
A blue short-sleeve chambray shirt crafted from stretchy, moisture-wicking cotton blend for breathable comfort.
(625)
$59.95 $39.99
SALE
$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 white, midweight cotton flannel shirt, brushed inside and out, with button-close chest pockets.
(531)
$79.95 $49.99
SALE
$79.95 $49.99
SALE
Men's Comfort Stretch® Oxford Shirt, Traditional Fit
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Traditional Fit
A blue cotton-blend Oxford shirt with stretch, moisture-wicking performance and an easy-care, untucked design.
(290)
$74.95 $54.99
SALE
What customers like:
Quality fabric
Versatile
Good fit
Dressy yet comfortable
Casual style
$74.95 $54.99
SALE
Women's Signature Rangeley Cotton Tee, Henley
L.L.Bean Women's Signature Rangeley Cotton Tee, Henley
A fitted blue cotton tee with a button-front henley placket and smooth jersey-knit comfort.
(192)
$54.95 $19.99
SALE
What customers like:
Feels good and great warmth
Great winter weight
Favorite tee
Comfort
Cute print
$54.95 $19.99
SALE
Men's Tropicwear Shirt, Plaid Long-Sleeve
L.L.Bean Men's Tropicwear Shirt, Plaid Long-Sleeve
A blue plaid, lightweight synthetic-nylon shirt with UPF 50+ sun protection, stretch, venting and utility pockets.
(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 brown wool-nylon jac-shirt with an attached cape, rugged zipper and pockets for versatile warmth.
(126)
$190 $190
SALE
$190 $190
SALE
Men's Double L Field Shirt, Hunter Orange
L.L.Bean Men's Double L Field Shirt, Hunter Orange
A rugged hunter-orange upland shirt with articulated mobility, reinforced forearms, and durable cotton-acrylic fabric.
(81)
$89.95 $89.95
SALE
What customers like:
High quality
Good fit
Great warmth
Excellent cuff design
Ideal weight
$89.95 $89.95
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 green wool-nylon jac-shirt insulated with windproof 40-gram PrimaLoft Silver and featuring a protective wool cape.
(28)
$250 $250
SALE
What customers like:
Great fit
High quality
Non-itchy material
Excellent warmth
$250 $250
SALE
Women's Whisperweight Flannel Popover Shirt
L.L.Bean Women's Whisperweight Flannel Popover Shirt
A lightweight tan flannel shirt in 100% cotton twill, featuring a split neckline and curved hem.
(0)
$69.95 $39.99
SALE
$69.95 $39.99
SALE
Men's Cloud Gauze Shirt, Slightly Fitted, Long-Sleeve
L.L.Bean Men's Cloud Gauze Shirt, Slightly Fitted, Long-Sleeve
A lightweight white cotton gauze shirt with a breathable crinkled texture, button-down collar, and chest pocket.
(0)
$69.95 $34.99
SALE
$69.95 $34.99
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 textured shirt in a TENCEL™ Lyocell blend, featuring a relaxed fit and warm-weather print.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
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 brushed for softness, featuring a textured look and button-down collar.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted, Lined, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted, Lined, Plaid
A soft, rugged brown plaid cotton flannel with smooth jersey-knit lining, durable stitching and convenient pockets.
(0)
$110 $79.99
SALE
$110 $79.99
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Slightly Fitted, Long-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Slightly Fitted, Long-Sleeve
A brown, ultralight cotton-blend stretch shirt that wicks moisture, dries quickly, and wears tucked or untucked.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Sunwashed Corduroy Shirt, Slightly Fitted
L.L.Bean Men's Sunwashed Corduroy Shirt, Slightly Fitted
A white, lightweight cotton corduroy shirt washed for softness, with a slightly fitted, untucked-friendly design.
(0)
$64.95 $34.99
SALE
$64.95 $34.99
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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