Holiday Dress Shirts

Holiday dress shirts make every gathering feel a little more special. Whether you’re celebrating with family, attending a festive dinner, or enjoying seasonal traditions, the right shirt helps you look and feel your best. With styles designed for comfort and lasting value, our collection of holiday dress shirts is ready for every occasion on your calendar. Find versatile options that pair easily with your favorite pants or sweaters, so you can focus on making memories all season long.

Sort by:

Filter & Sort

476 Items

Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Price was from: $69.95 now: $58.99

A yellow check button-down shirt made of wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Attractive classic design Great fit and sizing Wrinkle-free and easy care Comfortable and lightweight High quality and durable
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free white oxford shirt in 100% cotton with a traditional fit and durable buttons.

Pros: High quality Perfect fit Wrinkle-free Professional look Versatile
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $69.95 now: $58.99

A yellow check button-down shirt made from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Attractive color and style Versatile and flattering design High quality construction Wrinkle-free fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit

A red cotton-blend oxford shirt with stretch, moisture-wicking TrueCool® fabric, and an untucked fit.

Pros: High material quality Well-made construction Attractive appearance Cute print Comfortable fit
Men's Scotch Plaid Flannel Shirt, Slightly Fitted
Price was from: $59.95 now: $49.99

A slightly fitted flannel shirt in antique dress stewart plaid, made from 100% Portuguese cotton.

Pros: High quality Stylish design Warmth Softness of fabric Comfortable fit
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.

Pros: Great fit High quality Wrinkle-free Versatile Comfortable
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check
Price was from: $59.95 now: $49.99

A deep green, wrinkle-free short-sleeve shirt in 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Wrinkle-free Great color Durable Comfortable Good fit
Men's Wrinkle-Free Classic Oxford Cloth Shirt, Traditional Fit University Stripe

A wrinkle-free, 100% cotton oxford shirt with a traditional fit and stylish French blue university stripes.

Pros: High quality Perfect fit Wrinkle-free Classic style Comfortable
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall
Price was from: $79.95 now: $67.99

A wrinkle-free, 100% cotton tattersall shirt with a traditional fit and ultrasmooth finish for all-day comfort.

Pros: High quality Wrinkle-free Easy to care for Durable Comfortable fit
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Short-Sleeve, Stripe
Price was from: $59.95 now: $50.99

A breathable red cotton-blend chambray shirt with built-in stretch and a relaxed, untucked fit.
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A versatile white oxford shirt with moisture-wicking cotton blend and stretch for ease of movement.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
Men's Comfort Stretch Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Stripe
Price was from: $74.95 now: $62.99

A blue striped chambray shirt in a breathable cotton blend with stretch and a modern untucked hem.

Pros: Modern untucked hem Easy to care for Stylish design Great fabric quality Comfortable fit
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $74.95 now: $59.99

A lightweight chambray shirt in a cotton blend with moisture-wicking, quick-drying fabric and untucked fit.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $38.99

A slim-fit walnut shirt made from a soft cotton blend with a button-down collar and chest pocket.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Print

A blue cotton blend shirt with moisture-wicking stretch fabric and a slightly fitted untucked design.
Men's Comfort Stretch Oxford Shirt, Slightly Fitted Untucked Fit, Stripe
Price was from: $74.95 now: $62.99

A green striped cotton-blend oxford shirt with stretch, moisture-wicking performance, and an untucked fit.
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.
Men's Brushed Jaspé Twill Shirt, Plaid, Traditional Untucked Fit
Price was from: $69.95 now: $44.99

A soft, red plaid cotton shirt with a relaxed fit and shorter hem for untucked wear.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A yellow cotton blend plaid shirt featuring quick-drying, moisture-wicking stretch fabric and hidden collar buttons.
Men's Comfort Stretch Performance® Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $64.95 now: $54.99

A yellow plaid short-sleeve shirt in lightweight cotton blend with quick-drying, moisture-wicking stretch fabric.
Men's Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
Price was from: $89 now: $74.99

A slim-fit purple oxford shirt crafted from 100% Pima cotton for luxurious softness and all-season comfort.
Men's Comfort Stretch Performance® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $64.95 now: $54.99

A green plaid cotton-blend shirt featuring quick-drying, moisture-wicking stretch chambray and a relaxed untucked fit.
Men's Comfort Stretch Oxford Shirt, Traditional Untucked Fit, Stripe
Price was from: $74.95 now: $62.99

A pink cotton-blend striped oxford shirt with stretch, moisture-wicking performance, and an untucked fit.
Men's Comfort Stretch Performance® Seersucker Shirt, Short-Sleeve, Slightly Fitted Untucked Fit, Stripe

A brown seersucker shirt in a cotton-nylon blend with moisture-wicking stretch and a slightly fitted untucked fit.

Holiday Dress Shirts

Holiday dress shirts have a special way of bringing people together, whether you’re gathering with family for a backyard celebration, attending a late-summer wedding, or planning a cozy dinner with friends as the evenings grow cooler. These shirts are designed to offer just the right blend of comfort, style, and versatility—making them a staple for anyone looking to look their best while still feeling at ease. Thoughtful details like crisp collars, quality buttons, and carefully chosen fabrics set ll bean dress shirts apart, ensuring they transition seamlessly from daytime festivities to evening events. Many people appreciate the easy-care nature of these shirts, with materials that resist wrinkles and hold their color, making them a smart choice for travel or busy schedules. Whether you prefer a classic solid, a subtle pattern, or a bold seasonal print, there’s a holiday dress shirt to match every personality and occasion.

Holiday dress shirts also make thoughtful gifts, especially for those who enjoy celebrating with a bit of extra flair or who take pride in their wardrobe. Giving an ll bean dress shirt is a way to share a sense of tradition and quality—something that can be worn for years to come and remembered for the moments it was part of. These shirts are popular with everyone from recent graduates heading to their first formal gatherings, to parents looking to refresh their seasonal wardrobe, to friends who appreciate a timeless, well-made piece. They’re equally at home layered under a sweater for a crisp, pulled-together look or worn open over a tee for a more relaxed holiday vibe. With fits and sizes designed to accommodate a variety of body types, llbean dress shirts are inclusive and accessible, making it easy to find the right style for anyone on your list.

As you browse for the perfect holiday dress shirts, consider the fabric weight and breathability if you’re planning for warmer celebrations, or look for cozier options as the temperature drops. Details like button-down collars, chest pockets, and tailored fits can add both function and personality, while durable stitching and quality materials ensure your shirt will last through many seasons of gatherings. For those who enjoy exploring different styles, there are plenty of options to mix and match with accessories or favorite layers. And if you’re searching for a complementary piece or want to see how these shirts can inspire other looks, take a moment to explore Holiday Shirt Dresses for even more seasonal inspiration. Whether you’re dressing up for a special event or simply want to add a touch of celebration to everyday moments, l l bean dress shirts are made for sharing the joy of the season—wherever you find yourself gathering, connecting, and making memories.

FAQs

Holiday dress shirts are often crafted from soft, breathable cotton, brushed flannel, or cotton blends that provide comfort and durability. These materials are chosen for their ability to hold color and shape, ensuring your shirt looks great throughout the season and beyond.

A holiday dress shirt is incredibly versatile. For casual gatherings, try pairing it with jeans or chinos and layering with a cozy sweater or vest. For more formal events, tuck it into dress pants and add a blazer or sport coat for a polished, festive look.

Yes, holiday dress shirts are designed to layer comfortably under sweaters, cardigans, or jackets. Their breathable fabrics and classic silhouettes make them ideal for adding warmth without sacrificing style during the colder months.

Classic patterns like plaid, checks, and subtle stripes are perennial favorites for holiday dress shirts. Rich, seasonal colors such as deep reds, greens, blues, and warm neutrals help capture the festive spirit and look great in family photos.

Absolutely. A well-made holiday dress shirt is a thoughtful and practical gift that suits a wide range of recipients. Its timeless style and lasting comfort make it a welcome addition to anyone’s winter wardrobe, perfect for both special occasions and everyday wear.

It's time to upgrade your browser

Holiday Dress Shirts