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Holiday Dress Shirts

Find holiday dress shirts for a polished holiday look, with classic styles that feel true to you. Browse with your outfit in mind, considering how the collar and overall look will pair with your dress pants, blazer or sweater.

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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, non-iron fabric and a relaxed traditional fit.
(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 durable, soft 100% cotton oxford shirt in blue university stripes features wrinkle-free fabric and traditional tailoring.
(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 100% cotton tattersall oxford shirt with a wrinkle-free finish and ultrasmooth feel.
(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 Classic Oxford Cloth Shirt, Traditional Fit
L.L.Bean Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit
A blue, wrinkle-free 100% cotton Oxford shirt featuring traditional fit, button-down styling and durable double-needle stitching.
(3,567)
$64.95 $64.95
SALE
What customers like:
Great fit
High quality
Wrinkle-free
Durable
Comfortable
$64.95 $64.95
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 button-down shirt with wrinkle-free performance and moisture-wicking, quick-drying comfort.
(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 cotton-blend shirt with stretch fabric that wicks moisture and dries quickly for comfortable wear.
(0)
$74.95 $74.95
SALE
$74.95 $74.95
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 and moisture-wicking, quick-drying comfort.
(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, Traditional Fit, Check
L.L.Bean Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit, Check
A blue checked cotton poplin shirt with moisture-wicking, wrinkle-free performance, button-down collar and chest pocket.
(4,814)
$69.95 $49.99
SALE
What customers like:
Fits well
Good quality
Bright and vivid colors
Wrinkle-free
Lightweight
$69.95 $49.99
SALE
Men's Comfort Stretch Oxford Shirt, Traditional Fit, Stripe
L.L.Bean Men's Comfort Stretch Oxford Shirt, Traditional Fit, Stripe
A pink striped oxford shirt in a 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® Oxford Shirt, Slightly Fitted, Stripe
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Slightly Fitted, Stripe
A blue striped cotton-blend oxford shirt with stretch, moisture-wicking performance, and an easy untucked design.
(0)
$74.95 $62.99
SALE
$74.95 $62.99
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 green cotton check shirt with wrinkle-free, moisture-wicking performance, a buttoned collar and front pocket.
(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 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 moisture-wicking, quick-drying stretch fabric, hidden collar buttons, and an untucked-friendly hem.
(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 green, slim-fitting cotton twill shirt with Donegal flecks, button-down collar, and a convenient chest pocket.
(0)
$79.95 $59.99
SALE
$79.95 $59.99
SALE
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Slightly Fitted
A red cotton-blend Oxford shirt with moisture-wicking stretch, easy-care performance and a polished untucked design.
(251)
$74.95 $54.99
SALE
What customers like:
High material quality
Well-made construction
Attractive appearance
Cute print
Comfortable fit
$74.95 $54.99
SALE
Men's Comfort Stretch® Oxford Shirt, Traditional Fit
L.L.Bean Men's Comfort Stretch® Oxford Shirt, Traditional Fit
A red cotton-blend shirt with moisture-wicking stretch, easy-care fabric, and a polished untucked design.
(290)
$74.95 $54.99
SALE
What customers like:
Looks good untucked
Versatile style
Available in tall sizes
High-quality fabric
Comfortable fit
$74.95 $54.99
SALE

Holiday Dress Shirts

Holiday Dress Shirts bring a sense of occasion to getting dressed, whether the calendar calls for a holiday dinner, an office celebration or an evening with friends. There’s something welcoming about a table set for company, familiar voices in the next room and an outfit that feels right for the gathering. Choosing a shirt starts with how dressed up you want to be and what you already enjoy wearing. A solid color offers a simple starting point, while a pattern can add interest alongside understated pants and a jacket. Think about the whole outfit rather than the shirt alone: the colors you reach for, the proportions you prefer and whether a tie will be part of the picture. The best choice is one that reflects the occasion without making you feel unlike yourself.

Fit deserves particular attention when shopping for a dress shirt. Compare the measurements and fit notes for each option with a shirt you already like, rather than relying on the size label alone. Pay attention to the neck, shoulders, chest and sleeve length, especially if you plan to button the collar or wear the shirt beneath a jacket. Consider how you prefer to wear the hem, too, and check the individual shirt’s length and styling details before deciding. For a holiday outfit with several pieces, keeping the combination simple can help: let a patterned shirt be the focal point, or use a solid shirt to complement a more distinctive tie or sweater. Review the care instructions as part of your decision. A shirt’s place in your wardrobe depends not just on how it looks at the gathering, but on whether its care requirements fit your routine afterward.

Dress shirts can also make thoughtful holiday gifts for someone who enjoys putting an outfit together or appreciates a little help refreshing their wardrobe. Start with what the recipient actually wears, rather than what you would choose for yourself. Notice whether they favor quieter colors or more expressive patterns, a closer silhouette or a roomier cut, and an open collar or a tie. If possible, confirm their measurements or the fit of a favorite shirt before making your selection. Those small details make a gift feel personal without requiring a dramatic change in style. As you browse Holiday Dress Shirts, keep both the celebration and the person in mind. A considered choice can feel just as fitting at a carefully arranged holiday table as it does among the familiar pieces already hanging in the closet.

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