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Untucked Button-Down Shirts for Casual Wear

Find untucked button-down shirts for casual wear that keep your look relaxed yet put together. Browse the selection for an everyday shirt with classic button-down style, designed to be worn untucked.

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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 relaxed blue cotton shirt with a playful print, pearlized buttons, and a wrinkle-resistant finish.
(2,754)
$79.95 $64.99
SALE
$79.95 $64.99
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 blue checked cotton button-down shirt with wrinkle-free, moisture-wicking fabric, short sleeves, and a buttoned collar.
(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 pinpoint oxford shirt with wrinkle-free fabric, ultrasmooth finish, and relaxed traditional fit.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Professional look
Versatile
$79.95 $79.95
SALE
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit, Tattersall
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit, Tattersall
A blue cotton tattersall shirt with wrinkle-free, non-iron fabric and an ultrasmooth, crisp finish.
(2,091)
$79.95 $79.95
SALE
What customers like:
High quality
Wrinkle-free
Easy to care for
Durable
Comfortable fit
$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, relaxed-fit cotton oxford shirt with wrinkle-resistant fabric, pearlized buttons, and smooth taped seams.
(2,043)
$79.95 $79.95
SALE
What customers like:
High quality
Easy care
Perfect fit
Wrinkle-free
Versatile
$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 colorful plaid, 100% cotton oxford shirt with wrinkle-free fabric, taped seams, and a relaxed fit.
(1,793)
$79.95 $54.99
SALE
What customers like:
High-quality material
Perfect fit
Wrinkle-free
Comfortable and durable
Versatile and classic look
$79.95 $54.99
SALE
Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
L.L.Bean Men's Sunwashed Canvas Shirt, Traditional Fit, Short-Sleeve
A prewashed orange cotton canvas shirt with rugged stitching, button-flap pockets, and a relaxed traditional fit.
(1,629)
$59.95 $50.99
SALE
What customers like:
Perfect fit
Durable and sturdy
Versatile style
Comfortable to wear
Soft fabric
$59.95 $50.99
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 check sport shirt in wrinkle-free cotton poplin with moisture-wicking performance and a button-down collar.
(1,619)
$69.95 $69.95
SALE
What customers like:
Great fit and true to size
Attractive color and style
Wrinkle-free and easy care
High quality and durable
Comfortable and lightweight fabric
$69.95 $69.95
SALE
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
L.L.Bean Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
A purple plaid cotton flannel shirt with a slim fit and brushed, garment-washed softness.
(1,273)
$89 $75.99
SALE
$89 $75.99
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 brown, moisture-wicking cotton-blend shirt with stretch, long sleeves, chest pocket, and an untucked-friendly hem.
(1,159)
$74.95 $54.99
SALE
$74.95 $54.99
SALE
Men's Tropicwear Shirt, Long-Sleeve
L.L.Bean Men's Tropicwear Shirt, Long-Sleeve
A blue, lightweight polyester-nylon shirt with UPF 50+ sun protection, stretch, venting and secure pockets.
(980)
$74.95 $74.95
SALE
What customers like:
Great fit
Light and comfortable wear
Good quality
Sun protection
Versatile
$74.95 $74.95
SALE
Men's SunSmart® Cool Weave Shirt Short-Sleeve
L.L.Bean Men's SunSmart® Cool Weave Shirt Short-Sleeve
A green, lightweight polyester-nylon shirt offering UPF 50+ sun protection, moisture-wicking performance and quick-drying comfort.
(600)
$59.95 $34.99
SALE
What customers like:
Cool-looking design
Excellent for summer
True to size
Good quality material
Comfortable fit
$59.95 $34.99
SALE
Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
L.L.Bean Men's 1912 Field Flannel Shirt, Slightly Fitted, Plaid
A rugged brown cotton flannel shirt with yarn-dyed plaid, brushed softness, durable stitching, and two button-closure chest pockets.
(531)
$79.95 $49.99
SALE
What customers like:
Great fit
High-quality material
Well-built
Very comfortable
Excellent return policy
$79.95 $49.99
SALE
Men's Tropicwear Shirt, Short-Sleeve
L.L.Bean Men's Tropicwear Shirt, Short-Sleeve
A gray, lightweight polyester-nylon shirt with UPF 50+ protection, stretch, venting and multiple secure pockets.
(461)
$69.95 $44.99
SALE
What customers like:
High quality
Great comfort
Attractive appearance
Durable material
Excellent fit
$69.95 $44.99
SALE
Women's No Fly Zone Shirt, Long-Sleeve
L.L.Bean Women's No Fly Zone Shirt, Long-Sleeve
A green stretch synthetic-nylon shirt with permethrin insect protection, UPF 50+ sun protection, and moisture-wicking comfort.
(396)
$99.95 $99.95
SALE
What customers like:
Sun protection
Stylish
Effective mosquito protection
Good fit
Comfortable
$99.95 $99.95
SALE
Men's Maine Guide Shirt
L.L.Bean Men's Maine Guide Shirt
A durable, full-cut plaid shirt in an 85% wool and 15% nylon blend, designed for layering or wearing tucked in.
(352)
$170 $170
SALE
What customers like:
Great fit
High quality
Good quality
Cushioning
Warm
$170 $170
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 No Fly Zone Shirt, Long-Sleeve
L.L.Bean Men's No Fly Zone Shirt, Long-Sleeve
A green synthetic-nylon shirt with insect-repellent, UPF 50+ protection, stretch comfort and moisture-wicking performance.
(284)
$99.95 $99.95
SALE
$99.95 $99.95
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 chambray shirt in stretchy cotton blend with moisture-wicking comfort and a shorter hem.
(267)
$74.95 $54.99
SALE
$74.95 $54.99
SALE
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Slightly Fitted
A blue cotton-blend Oxford shirt with stretch fabric that wicks moisture and dries quickly.
(251)
$74.95 $34.99
SALE
What customers like:
High material quality
Well-made
Cute print
Great appearance
Comfortable
$74.95 $34.99
SALE
Women's Signature Camp Shirt Dress, Button-Front
L.L.Bean Women's Signature Camp Shirt Dress, Button-Front
A breathable tan cotton shirt dress with a removable belt, pockets, roll-tab sleeves, and curved hem.
(191)
$119 $39.99
SALE
What customers like:
Simple yet chic
Timeless appeal
Thoughtful design
High-quality fabric
Elegant style
$119 $39.99
SALE
Men's Double L Field Shirt
L.L.Bean Men's Double L Field Shirt
A tan cotton canvas shirt with articulated movement, reinforced forearms, and durable construction for hunting.
(144)
$89.95 $89.95
SALE
What customers like:
Breathable fabric
Wind protection
Rugged design
Good fit
Casual style
$89.95 $89.95
SALE

Untucked Button-Down Shirts for Casual Wear

Untucked button-down shirts for casual wear bring together the familiar detail of a collared shirt and the relaxed look of a hem worn outside the waistband. The distinction is in the proportions: a shirt intended to stay untucked generally has less length through the body than a traditional dress shirt, so the hem looks like part of the outfit rather than something left unfinished. A straight or gently curved hem can create a clean outline, while longer, deeply curved shirttails tend to give a different impression when left out. As a general point of comparison, an untucked hem often falls below the waistband and somewhere around the middle of the pants zipper, with the back resting partway over the back pockets. Those landmarks are starting points, not fixed rules; torso length, pants rise, shirt size and personal preference all influence where a hem lands. The most natural result is a shirt that looks balanced from the front, side and back, without an expanse of fabric covering most of the pants. That balance gives casual button-down shirts their appeal. A collar and a row of buttons lend definition, while the untucked silhouette keeps the overall look easygoing. With jeans, the effect is familiar and straightforward; with chinos, the same general shape can feel a little more put together without becoming formal. Solid colors keep the focus on the silhouette, while checks and stripes add visual interest. Smaller patterns tend to read more quietly from a distance, and larger patterns make the shirt a stronger part of the outfit. Personal taste matters more than a rigid styling formula. For a closer look at this category, Men's Casual Untucked Shirts brings the focus to a wardrobe staple with an intentionally untucked look. The appeal is a familiar style that leaves room for individual expression, whether the preference is understated or more colorful.

Fit gives an untucked button-down much of its character, and the size label tells only part of that story. Shoulder placement, body width, sleeve length and hem length work together to determine how the shirt looks on an individual person. For a conventional shoulder shape, the seam generally sits near the point where the shoulder meets the arm, rather than noticeably up toward the neck or down the upper arm. Through the chest, a button front that lies flat creates a cleaner line than one that pulls into gaps. Extra fabric through the sides changes the silhouette, too: a closer outline has a different visual effect from a fuller, more relaxed shape. Neither is automatically the better choice, but each should look intentional. An untucked shirt also needs to be considered at its actual wearing length. Going up a size simply to gain room can add length as well as width, so comparing the stated fit and measurements is more useful than assuming a larger size will solve every fit concern. A familiar shirt with a well-liked fit can provide a helpful reference for body length and chest measurements, provided the measurements are taken the same way as those in the size information. Sleeve proportions deserve similar attention. On a long-sleeve style, the cuff’s position at the wrist affects the overall outline, especially when the shirt is worn fully buttoned at the cuffs. Details such as collar size, pocket placement and the shape of the lower hem can make two shirts with similar measurements look quite different. The relationship to the pants matters as well. A fuller shirt over a narrower leg draws attention to the upper half of an outfit, while straighter proportions create a different balance. These are choices of style rather than rules to follow. A casual shirt should feel like a natural extension of the wearer’s taste, not a reason to rethink an entire wardrobe.

Beyond the silhouette, the smaller details help distinguish one casual button-down from another. The spacing of a check, the contrast in a stripe, the presence of a chest pocket and the appearance of the buttons all contribute to the finished look. A quiet pattern can sit comfortably alongside other familiar wardrobe pieces, while a bolder design may be the detail that gives an otherwise simple outfit its personality. Looking at a shirt both close up and as a complete outfit helps put those details in perspective. A pattern that appears prominent in a close photograph may look much subtler at a normal conversational distance. Material composition and care information are important comparison points, but they belong to the individual shirt rather than to the untucked category as a whole. The shape of the hem does not establish what a shirt is made from, how it should be washed or whether it needs a particular finishing step. Those details are best checked in the individual description and care label. A care routine that fits the owner’s habits is worth considering alongside color and fit; a shirt’s place in the wardrobe depends partly on whether its upkeep suits everyday life. Durability likewise cannot be judged from the untucked silhouette alone. Construction information, stated care requirements and attention to the condition of seams and buttons provide more useful context than broad promises about how long any shirt will last. For someone choosing a gift, a favorite shirt already in the recipient’s wardrobe can offer clues about preferred size, pattern scale and overall shape. A person who consistently chooses simple solids may appreciate that same understated direction, while someone drawn to checks may welcome a familiar pattern in a different arrangement. It also helps to distinguish between a preference for wearing shirts untucked and a preference for a particular fit; the two do not necessarily mean the same thing. Ultimately, the strongest choice combines a pleasing proportion, a design that feels personal and clear individual product information. Untucked button-down shirts offer a timeless approach to casual wear: enough detail to make an outfit feel considered, without making it feel dressed up.
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