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Men's Holiday Dress Shirts

Find men's holiday dress shirts for holiday dinners, parties and family gatherings. Explore classic styles to complement your holiday outfit, whether you're pairing a shirt with dress pants or adding a blazer for a more dressed-up look.

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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 red check cotton poplin shirt offering wrinkle-free performance, moisture-wicking comfort, and classic button-down style.
(4,814)
$69.95 $69.95
SALE
What customers like:
Comfortable fit and feel
High quality and durable fabric
Wrinkle-free and easy care
Attractive colors and pattern
Classic style and versatile design
$69.95 $69.95
SALE
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
A wrinkle-free white oxford shirt with a traditional fit, crafted from 100% cotton for ultimate comfort.
(3,567)
$64.95 $64.95
SALE
What customers like:
Great fit
High quality
Wrinkle-free
Versatile
Comfortable
$64.95 $64.95
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 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 Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit
A wrinkle-free white cotton shirt offering a relaxed traditional fit and ultrasmooth finish.
(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 Classic Oxford Cloth Shirt, Traditional Fit University Stripe
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe
A wrinkle-free, 100% cotton oxford shirt with French blue university stripes and a traditional fit.
(2,141)
$64.95 $64.95
SALE
What customers like:
High quality
Perfect fit
Wrinkle-free
Classic style
Comfortable
$64.95 $64.95
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 tattersall shirt in crystal blue with a traditional fit for all-day comfort.
(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
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 button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.
(1,619)
$69.95 $69.95
SALE
What customers like:
Attractive color and style
Wrinkle free and easy care
Good fit and true to size
High quality and durable
Comfortable and lightweight fabric
$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 chambray shirt with moisture-wicking cotton blend and stretch for comfort, perfect untucked.
(1,214)
$69.95 $49.99
SALE
What customers like:
Great fit
High quality
Attractive color
Versatile design
Excellent comfort
$69.95 $49.99
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 oxford shirt with moisture-wicking, stretch 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 a modern untucked hem.
(267)
$74.95 $62.99
SALE
What customers like:
Modern untucked hem
Easy to care for
Stylish design
Great fabric quality
Comfortable fit
$74.95 $62.99
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Long-Sleeve, Slim Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Long-Sleeve, Slim Fit, Check
A green slim-fit cotton poplin shirt offering wrinkle-free performance and moisture-wicking comfort.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
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, and stretch fabric.
(0)
$74.95 $59.99
SALE
$74.95 $59.99
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 pink plaid seersucker shirt in a cotton-nylon blend with moisture-wicking stretch and hidden collar buttons.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
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 long-sleeve shirt featuring quick-drying, moisture-wicking stretch chambray and hidden collar buttons.
(0)
$64.95 $64.95
SALE
$64.95 $64.95
SALE
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
L.L.Bean Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
A slim-fit oxford shirt crafted from 100% Pima cotton for exceptional softness and year-round comfort.
(0)
$89 $74.99
SALE
$89 $74.99
SALE
Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
A green plaid cotton-blend shirt featuring quick-drying, moisture-wicking stretch chambray and a relaxed untucked fit.
(0)
$64.95 $44.99
SALE
$64.95 $44.99
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 moisture-wicking stretch fabric and a slightly fitted untucked design.
(0)
$79.95 $79.95
SALE
$79.95 $79.95
SALE
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
L.L.Bean Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
An extra-soft, slim-fit shirt in emerald spruce, made from a comfortable cotton blend with a button-down collar.
(0)
$79 $38.99
SALE
$79 $38.99
SALE
Men's Comfort Stretch Performance® Button-Front Knit Shirt, Long-Sleeve
L.L.Bean Men's Comfort Stretch Performance® Button-Front Knit Shirt, Long-Sleeve
A lightweight blue shirt in a moisture-wicking Pima cotton and polyester blend with a button-down collar.
(0)
$89.95 $89.95
SALE
$89.95 $89.95
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, Plaid
L.L.Bean Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
A yellow cotton blend plaid shirt featuring quick-drying, moisture-wicking stretch fabric and hidden collar buttons.
(0)
$74.95 $59.99
SALE
$74.95 $59.99
SALE
Men's Brushed Jaspé Twill Shirt, Plaid, Traditional Untucked Fit
L.L.Bean Men's Brushed Jaspé Twill Shirt, Plaid, Traditional Untucked Fit
A red plaid cotton shirt with a relaxed fit, perfect for untucked wear and year-round comfort.
(0)
$69.95 $44.99
SALE
$69.95 $44.99
SALE
Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
L.L.Bean Men's Sunwashed Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
A green plaid oxford shirt made from 100% cotton, washed for extra softness and comfort.
(0)
$69.95 $69.95
SALE
$69.95 $69.95
SALE
Men's Comfort Stretch Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
L.L.Bean Men's Comfort Stretch Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
A green striped cotton-blend oxford shirt with stretch, moisture-wicking performance, and an untucked fit.
(0)
$74.95 $62.99
SALE
$74.95 $62.99
SALE

Men's Holiday Dress Shirts

Men's Holiday Dress Shirts bring a little extra occasion to the familiar pleasure of gathering with friends and family. When the table is set, the coats are piled by the door and everyone is catching up, a thoughtfully chosen shirt feels right at home. Start with the kind of holiday dressing you enjoy: understated and traditional, rich in seasonal color or brightened by a favorite pattern. A solid shirt offers a simple foundation, while stripes and checks add another point of interest. Consider what is already in your closet, too. A color that complements your favorite trousers or jacket gives you a clear starting point for the whole outfit. There is no need to choose something that feels unlike you just because the occasion is special; often, the best choice is a slightly more dressed-up expression of your own style.

Fit deserves as much attention as color and pattern when choosing a holiday dress shirt. Compare the listed measurements and sizing information with a shirt you already like wearing, paying particular attention to the neck, shoulders, chest and sleeve length. Look at how the collar sits when buttoned, where the shoulder seams fall and whether the cuffs finish where you prefer them. If you plan to tuck the shirt in, check the length rather than relying on the size label alone. Think through the small details of your outfit before deciding: a collar worn open creates a different look from one paired with a tie, and a pattern that looks subtle on its own may feel busier beside a patterned jacket. Product photos, fit descriptions and care instructions can help narrow your choices. These details are worth a few extra minutes, especially when you want getting dressed to be the easy part of a full holiday calendar.

A holiday dress shirt can also make a thoughtful gift for someone who enjoys choosing an outfit for the occasion. The most useful clues are often the simplest: the colors he reaches for, whether he favors solids or patterns, and the fit of the shirts he wears most. A spouse, partner, father, brother or friend may appreciate a familiar style in a different color more than a complete departure from his usual wardrobe. If you can, confirm his measurements instead of guessing, and consider his preferences about care as well as appearance. Picture the details he would choose for himself—the open collar, the neatly buttoned cuffs, the quiet pattern beneath a favorite sweater. Choosing with those preferences in mind makes the gift personal without making it complicated, and keeps the focus where it belongs: on someone you know well and the holiday moments you share.

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