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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 checked 100% cotton poplin sport shirt with wrinkle-free, moisture-wicking performance and button-down collar.
(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 white, wrinkle-free 100% cotton Oxford shirt with traditional fit, classic tailoring and button-down styling.
(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 green cotton check shirt with wrinkle-free, moisture-wicking fabric, a buttoned collar and traditional relaxed 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 blue, 100% cotton pinpoint oxford shirt with wrinkle-free fabric, traditional fit, and durable tailored construction.
(2,511)
$79.95 $79.95
SALE
What customers like:
High quality
Easy care
Perfect fit
Wrinkle-free
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 blue, wrinkle-free cotton Oxford shirt with university stripes, traditional fit, gentle collar roll and durable double-needle stitching.
(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 blue cotton tattersall shirt with wrinkle-free fabric, traditional fit, and an ultrasmooth, crisp finish.
(2,091)
$79.95 $79.95
SALE
What customers like:
Durable construction
Wrinkle-free quality
High-quality materials
Professional look
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 green cotton check shirt with wrinkle-free performance, moisture-wicking fabric, and a button-down collar.
(1,619)
$69.95 $69.95
SALE
What customers like:
Versatile color
Flattering design
High-quality fabric
Wrinkle-free performance
Comfortable fit
$69.95 $69.95
SALE
Men's Wrinkle-Free Kennebunk Sport Shirt, Slim Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Slim Fit, Check
A green, slim-fitting cotton check shirt with wrinkle-free performance and moisture-wicking, quick-drying TrueCool® fabric.
(0)
$59.95 $59.95
SALE
$59.95 $59.95
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 shirt in lightweight cotton-blend stretch fabric that wicks moisture and dries quickly.
(0)
$74.95 $59.99
SALE
$74.95 $59.99
SALE
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted, Stripe
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Slightly Fitted, Stripe
A blue striped oxford shirt in stretchy cotton blend fabric that wicks moisture and dries quickly.
(0)
$74.95 $62.99
SALE
$74.95 $62.99
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, lightweight cotton-blend shirt with moisture-wicking, quick-drying stretch fabric and hidden collar buttons.
(0)
$74.95 $49.99
SALE
$74.95 $49.99
SALE
Men's Signature Donegal Woven Shirt, Slim Fit
L.L.Bean Men's Signature Donegal Woven Shirt, Slim Fit
A rugged green twill flannel shirt with Donegal flecks, button-down collar, chest pocket and cotton construction.
(0)
$79.95 $59.99
SALE
$79.95 $59.99
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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