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Relaxed Fit Button-Down Shirts

Find relaxed fit button-down shirts with a roomy silhouette and classic button-front styling. Browse the selection for a look you like, and compare individual fit details to choose a shirt with the amount of room you prefer.

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Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
L.L.Bean Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth
A warm red houndstooth flannel shirt in brushed cotton that resists shrinking, wrinkling and pilling.
(8,393)
$79.95 $54.99
SALE
What customers like:
Great quality
Softness
Warmth
Nice color
Comfortable fit
$79.95 $54.99
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 Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit, Check
A blue cotton check shirt featuring wrinkle-free, moisture-wicking TrueCool® fabric and a classic button-down collar.
(4,814)
$69.95 $69.95
SALE
$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 blue checked cotton sport shirt with wrinkle-free, moisture-wicking performance, buttoned collar, and traditional relaxed fit.
(2,628)
$59.95 $59.95
SALE
$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 button-down shirt with wrinkle-free fabric, traditional relaxed fit, and durable tailoring.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Professional look
Versatile
$79.95 $79.95
SALE
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit
L.L.Bean Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit
A white cotton oxford shirt with a relaxed fit and wrinkle-resistant finish for easy care.
(2,043)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit Plaid
L.L.Bean Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit Plaid
A blue plaid, wrinkle-free cotton shirt with long sleeves, relaxed fit, taped seams and pearlized buttons.
(1,793)
$79.95 $79.95
SALE
$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 blue checked cotton shirt with wrinkle-free, moisture-wicking 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, Long-Sleeve
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Fit, Long-Sleeve
A blue cotton-blend shirt with stretch, moisture-wicking performance, and a shorter untucked-friendly hem.
(1,214)
$69.95 $49.99
SALE
What customers like:
High quality
Versatile design
Good color options
Soft fabric
Comfortable fit
$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, long sleeves and a versatile untucked fit.
(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 brown plaid cotton-blend shirt with stretch, moisture-wicking comfort, and a shorter untucked-friendly hem.
(845)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Women's Tropicwear Shirt, Short-Sleeve
L.L.Bean Women's Tropicwear Shirt, Short-Sleeve
A white, lightweight nylon-polyester shirt with stretch, UPF 50+ sun protection, venting, and wrinkle-free convenience.
(557)
$69.95 $44.99
SALE
What customers like:
Lightweight material
Perfect for hot days
True to size
Great color and quality
Comfortable fit
$69.95 $44.99
SALE
Men's Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve, Print
L.L.Bean Men's Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve, Print
A blue cotton-blend shirt with stretchy, moisture-wicking fabric that dries quickly and wears comfortably untucked.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Women's Camden Hills Button Front Shirt, Print
L.L.Bean Women's Camden Hills Button Front Shirt, Print
A white printed shirt in TENCEL™ blend jersey with a relaxed drape, button front, and shirred shoulders.
(0)
$69.95 $49.99
SALE
$69.95 $49.99
SALE
Women's Camden Hills Tee, Elbow-Sleeve Button-Front Shirt Print
L.L.Bean Women's Camden Hills Tee, Elbow-Sleeve Button-Front Shirt Print
A blue printed tee in soft TENCEL™ Lyocell-blend jersey, featuring elbow-length sleeves and a button-front placket.
(0)
$54.95 $34.99
SALE
$54.95 $34.99
SALE
Women's Essential Cotton Shirt, Chambray Long Sleeve
L.L.Bean Women's Essential Cotton Shirt, Chambray Long Sleeve
A lightweight blue 100% cotton chambray shirt with relaxed fit, curved hem, pocket and buttoned cuffs.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
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 blue long-sleeve shirt in stretchy cotton-blend chambray fabric that wicks moisture and dries quickly.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Women's Whisperweight Flannel Shirt, Button-Down
L.L.Bean Women's Whisperweight Flannel Shirt, Button-Down
A lightweight blue cotton flannel shirt with a relaxed fit and curved high-low hem.
(0)
$69.95 $39.99
SALE
$69.95 $39.99
SALE
Men's Riverton Ripstop Shirt, Traditional Fit, Long-Sleeve
L.L.Bean Men's Riverton Ripstop Shirt, Traditional Fit, Long-Sleeve
A blue cotton-blend ripstop shirt with stretch, garment-washed softness, and two practical button-front pockets.
(0)
$79.95 $54.99
SALE
$79.95 $54.99
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 Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve
A blue cotton-blend shirt with stretch fabric that wicks moisture and dries quickly for everyday wear.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
SALE
Men's Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch Performance® Shirt, Slightly Fitted, Long-Sleeve, Plaid
A blue plaid cotton-blend shirt with stretch, moisture-wicking, quick-drying performance fabric and a versatile untucked design.
(0)
$74.95 $59.99
SALE
$74.95 $59.99
SALE
Women's Signature Soft Poplin Shirt
L.L.Bean Women's Signature Soft Poplin Shirt
A relaxed white cotton-poplin shirt with a high-low hem and oversized front pockets.
(0)
$99 $34.99
SALE
$99 $34.99
SALE

Relaxed Fit Button-Down Shirts

Relaxed fit button-down shirts bring together a roomier silhouette and the familiar structure of a collared shirt. The defining feature is the fit: relaxed describes a cut with more room through the body than a closely fitted shape, though the exact proportions depend on the design. That distinction matters because a relaxed fit is not simply a larger size. Sizing up changes several measurements at once, while a shirt designed with relaxed proportions establishes that shape within its own size range. For someone who prefers a less fitted look, the starting point is the relationship between the shoulders, chest, waist, and hem rather than the size label alone. A shirt can look roomy through the middle without looking oversized everywhere, and two shirts marked relaxed may still sit differently on the same person. Shoulder construction, sleeve shape, and body length all contribute to the overall outline. Product measurements and fit descriptions offer a clearer picture than assuming the word relaxed means dropped shoulders, an extra-long hem, or a particular sleeve width. Comparing those details with a favorite shirt can help make the differences more concrete. Lay that shirt flat, fasten the front, and compare measurements taken in the same way as the listed sizing information. Notice where the shoulder seam falls, how much room sits through the chest, and where the hem ends. These small reference points help distinguish a pleasantly roomy shape from proportions that simply feel unfamiliar. The neckline deserves attention, too, especially for anyone who prefers the top button fastened. A relaxed body does not automatically mean a roomier collar. Taken together, these details make fit a matter of proportion and personal preference, not a rule about how closely a shirt should follow the body. The appeal is a recognizable shirt style with a little more space in its silhouette.

The button-down part of the name adds another point of distinction. Traditionally, a button-down shirt has collar points that fasten to the shirt with small buttons; button-up describes a front that closes with buttons. The terms are often used interchangeably, so the photographs and individual descriptions are useful for understanding the collar construction. Beyond that detail, the character of a shirt comes from the balance of its elements. Collar size, button placement, pockets, cuffs, and the line of the hem can make two similarly proportioned shirts look quite different. A smaller collar creates a different visual balance from a broader one, just as a plain front looks different from a front with prominent pockets. Patterns also change the impression of a relaxed silhouette. A fine pattern can read almost like a solid from a distance, while a larger pattern becomes a more noticeable part of the outfit. Neither approach is more correct; the better choice is the one that feels at home alongside the rest of a wardrobe. Someone who favors simple trousers and understated accessories might enjoy making the shirt the focal point, while someone drawn to a quieter look may prefer less contrast. Looking at familiar outfits is often more useful than imagining an entirely new wardrobe around one shirt. The proportions of the other pieces matter as well: a roomier shirt above a straighter trouser leg creates a different outline from loose proportions throughout. These are visual choices rather than fixed styling rules. Photos showing both the front and back can reveal how the shirt’s shape carries through the shoulders and hem, while closer views help clarify smaller details. Fabric composition is another worthwhile point of comparison, but the relaxed fit label does not identify a particular material. The individual description is the place to find that information rather than drawing conclusions from the silhouette or a photograph. Keeping fit, appearance, and fabric details separate makes it easier to see what actually distinguishes one design from another.

A thoughtfully chosen shirt should reflect the preferences of the person wearing it, including how much attention they want to give its care. Before choosing, read the garment’s care instructions and consider how they fit into an established laundry routine. Washing, drying, ironing, and any special handling requirements are details to verify for each shirt, not assumptions to make from the category name. Appearance in a photograph cannot establish how a garment should be washed or how it will look afterward. Following the stated instructions also avoids treating every collared shirt alike when their care requirements may differ. For questions about construction and durability, look for concrete information in the individual description rather than treating a relaxed cut as evidence of either. Close-up images can make seams, button attachments, and finishing details easier to examine, but they are not a substitute for stated product information. This same attention to particulars is helpful when choosing a shirt as a gift. A recipient’s favorite shirt can offer useful clues about preferred body length, collar shape, patterns, and overall proportions, provided its size is considered alongside the relevant size chart. A familiar size label alone may not capture the fit they enjoy. Some people consistently choose extra room through the body; others prefer a more defined shoulder line within a relaxed shape. Recognizing those preferences makes the choice feel personal without requiring a dramatic departure from their usual style. For a more focused selection, explore Men’s Relaxed Fit Button-Ups and compare the individual fit details with those preferences in mind. Whether choosing for someone else or refining a personal wardrobe, the most useful comparisons remain straightforward: the proportions, the collar, the length, the appearance, and the care requirements. Relaxed fit button-down shirts offer a familiar starting point, with room for individual taste in the details. A considered choice comes from understanding those details together, so the finished look feels like a natural expression of the person wearing it.
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