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Men's Stretch Button Down Shirts

Find men's stretch button down shirts that pair classic button-down style with added stretch. Browse the selection and compare each shirt’s fit, fabric and care details to find an option that works with your wardrobe.

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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 deep green, 100% cotton poplin shirt with wrinkle-free performance and moisture-wicking TrueCool® fabric.
(4,814)
$69.95 $58.99
SALE
What customers like:
Lightweight fabric
High quality
Wrinkle-free performance
Stylish appearance
Comfortable fit
$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 wrinkle-free, 100% cotton poplin shirt in Bering Blue with moisture-wicking TrueCool® fabric and a relaxed fit.
(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 Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
A wrinkle-free, 100% cotton shirt in crystal blue tattersall with a traditional, relaxed fit.
(2,091)
$79.95 $79.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Comfort
Durability
$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 slightly fitted, wrinkle-free cotton shirt in nautical blue check with moisture-wicking TrueCool® fabric.
(1,619)
$69.95 $69.95
SALE
What customers like:
High quality
Attractive color
Wrinkle-free fabric
Comfortable fit
No ironing needed
$69.95 $69.95
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
A green cotton blend shirt with built-in stretch, perfect for untucked wear and easy movement.
(1,214)
$69.95 $49.99
SALE
What customers like:
Great fit
High quality
Versatile design
Excellent comfort
Soft fabric
$69.95 $49.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
A vintage indigo chambray shirt with moisture-wicking cotton blend and built-in stretch for ultimate comfort.
(1,159)
$74.95 $54.99
SALE
What customers like:
High quality
Soft material
True to size
Comfortable
Well made
$74.95 $54.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Plaid
A blue cotton-blend plaid shirt offering breathable, moisture-wicking comfort with built-in stretch and a relaxed fit.
(845)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Short-Sleeve
An indigo short-sleeve chambray shirt with moisture-wicking cotton blend and built-in stretch for comfort.
(625)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit
A light cobalt cotton blend shirt with moisture-wicking fabric and a relaxed untucked fit.
(290)
$74.95 $54.99
SALE
What customers like:
Quality fabric
Versatile
Good fit
Dressy yet comfortable
Casual style
$74.95 $54.99
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 moisture-wicking comfort.
(267)
$74.95 $62.99
SALE
What customers like:
Easy to care for
Stylish design
Breathable and stretchy
Great fabric quality
Comfortable fit
$74.95 $62.99
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 untucked oxford shirt with moisture-wicking cotton blend and stretch for comfort.
(251)
$74.95 $54.99
SALE
What customers like:
Good appearance
High material quality
Well-made
Cute print
Comfortable
$74.95 $54.99
SALE
Men's Tropicwear Shirt, Plaid Short-Sleeve
L.L.Bean Men's Tropicwear Shirt, Plaid Short-Sleeve
A blue plaid short-sleeve shirt with UPF 50+ protection and wrinkle-free, stretchable fabric.
(143)
$74.95 $74.95
SALE
What customers like:
Great fit
Attractive appearance
Fast drying
Lightweight
Quick-drying
$74.95 $74.95
SALE
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
A blue cotton blend shirt with moisture-wicking fabric, perfect for untucked wear and easy care.
(0)
$59.95 $29.99
SALE
$59.95 $29.99
SALE
Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
L.L.Bean Men's Signature Stretch Poplin Shirt, Short-Sleeve, Slim Fit
An orange slim-fit shirt in a soft cotton blend, perfect for casual wear and easy care.
(0)
$69.95 $34.99
SALE
$69.95 $34.99
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
A green cotton-blend plaid shirt featuring quick-drying, moisture-wicking stretch chambray and a relaxed untucked fit.
(0)
$54.95 $34.99
SALE
$54.95 $34.99
SALE
Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
L.L.Bean Men's Comfort Stretch® Chambray Shirt, Slightly Fitted Untucked Fit, Short-Sleeve, Plaid
A vintage indigo plaid chambray shirt with built-in stretch, designed for comfort and untucked wear.
(0)
$59.95 $39.99
SALE
$59.95 $39.99
SALE
Men's Comfort Stretch Performance® Seersucker Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Comfort Stretch Performance® Seersucker Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
A blue plaid seersucker shirt in a moisture-wicking cotton blend with built-in stretch for comfort.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
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 $59.99
SALE
$74.95 $59.99
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
A blue cotton-blend chambray shirt featuring quick-drying, moisture-wicking stretch fabric and a relaxed fit.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Stripe
L.L.Bean Men's Stonecoast Hemp Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Stripe
A rugged, breathable gray shirt with a soft hemp/cotton blend and vintage-inspired stripes.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
SALE
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
L.L.Bean Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
A collegiate blue slim-fit shirt made from a soft cotton blend with a button-down collar and chest pocket.
(0)
$79 $38.99
SALE
$79 $38.99
SALE
Men's Mountainside Brushed Performance Shirt
L.L.Bean Men's Mountainside Brushed Performance Shirt
A blue synthetic flannel shirt offering UPF 50+ sun protection, moisture-wicking comfort, and superior stretch.
(0)
$89.95 $75.99
SALE
$89.95 $75.99
SALE
Men's Ultralight Trail Shirt, Short-Sleeve
L.L.Bean Men's Ultralight Trail Shirt, Short-Sleeve
A lightweight blue short-sleeve shirt with breathable, quick-drying synthetic fabric and zippered chest pocket.
(0)
$74.95 $74.95
SALE
$74.95 $74.95
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Short-Sleeve, Slightly Fitted Untucked Fit
A blue cotton-blend short-sleeve shirt featuring quick-drying, moisture-wicking stretch chambray for everyday comfort.
(0)
$54.95 $54.95
SALE
$54.95 $54.95
SALE

Men's Stretch Button Down Shirts

Men's Stretch Button Down Shirts bring a familiar look and a little extra give to a well-rounded wardrobe. There’s something appealing about the straightforward details of a button-down shirt: a neat collar, a row of buttons and a pattern or solid color that feels like you. Stretch adds another consideration alongside those classic elements, making it worth looking closely at both the cut and the individual shirt’s description. Start with the shape you already like to wear. A closer fit creates a trim outline, while a roomier cut leaves more space through the chest and waist. Neither is the right choice for everyone, and stretch shouldn’t be a reason to choose a size that’s too small. Compare the size chart with your measurements, then check any available fit notes. The goal is a shirt that sits naturally across your shoulders, buttons without pulling and has proportions that feel right for you.

The smaller details can make the difference between a shirt you admire and one you reach for again and again. Consider the collar’s shape, the placement of a chest pocket and the scale of a plaid or check. A fine pattern has a quieter presence; a larger one makes a more noticeable part of an outfit. Solid colors offer another straightforward option, especially when you prefer to keep the overall look simple. Picture the shirt beside the pants already in your closet rather than choosing it in isolation. If you like an untucked look, pay attention to the hem shape and length; if you prefer to tuck your shirts in, check that the length suits that preference. For long-sleeve styles, sleeve length and cuff fit deserve a close look, too. These are practical details, but they’re also what help a shirt feel like a natural part of your personal style.

When comparing stretch button-down shirts, read the individual fabric and care information rather than assuming every option has the same feel or needs the same care. The amount of stretch can differ, and the word “stretch” alone doesn’t tell you everything about a shirt’s weight, texture or fit. Think about what you appreciate in the shirts you already own—the shape of a favorite collar, a sleeve that lands just where you like it, or a pattern that pairs easily with nearly everything else. Those familiar details are useful starting points when choosing a gift as well. For a partner, father, brother or friend who enjoys button-down styles, take your cues from what they actually wear. A familiar fit and a thoughtfully chosen pattern can feel more personal than something far outside their usual taste. Keep the recipient’s sizing and care preferences in mind, and let their style lead the choice.

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