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

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 Kennebunk Sport Shirt, Slightly Fitted Check

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 Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $44.99

A wrinkle-free, vintage indigo shirt in ultrasoft brushed cotton with a slightly fitted, untucked design.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Nice color
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $36.99

A slightly fitted plaid oxford shirt in soft juniper, made from a moisture-wicking cotton blend.

Pros: High quality fabric Perfect fit Comfort Wrinkle-free after washing Untucked design
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 Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Short-Sleeve Check

A blue check short-sleeve shirt crafted from wrinkle-free, moisture-wicking cotton poplin for lasting comfort.

Pros: Wrinkle-free and stays crisp Great fit and true to size Lightweight and breathable for summer Very comfortable and soft fabric Attractive color and print options
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free, 100% cotton shirt in blue with a traditional fit and nearly custom sizing.

Pros: High quality Perfect fit Wrinkle-free Versatile Comfortable
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit Tattersall

A wrinkle-free, 100% cotton shirt in crystal blue tattersall with a traditional fit for all-day comfort.

Pros: High quality Wrinkle-free Easy to care for Durable Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $54.99

A breathable, moisture-wicking plaid chambray shirt with built-in stretch and a slightly fitted untucked fit.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $54.99

A slim fit, emerald spruce 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
Price was from: $79.95 now: $59.99

A lightweight chambray shirt in a cotton blend with moisture-wicking, quick-drying fabric and untucked fit.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A pink plaid shirt in a cotton blend with moisture-wicking, quick-drying fabric and hidden collar buttons.

Holiday Dress Shirts

When the holiday season arrives, there’s something special about reaching for a well-made dress shirt that brings a touch of comfort and celebration to every gathering. Whether you’re preparing for a family dinner, attending a neighborhood open house, or joining friends for a festive evening out, a quality holiday dress shirt helps set the tone for the occasion. These shirts are designed to balance timeless style with practical features, making them easy to wear from morning to night. Soft, breathable fabrics ensure all-day comfort, while thoughtful details like carefully stitched collars, durable buttons, and easy-to-care-for materials mean you can focus on enjoying the festivities rather than fussing over your outfit. Many people find that a classic dress shirt is a versatile staple, ready to pair with everything from cozy sweaters and vests to favorite slacks or jeans—ideal for both casual get-togethers and more formal celebrations. For those who appreciate lasting value, a well-chosen holiday dress shirt is a reliable addition to the wardrobe, ready to be pulled out year after year as part of your seasonal traditions.

Holiday dress shirts also make thoughtful gifts that are sure to be appreciated by anyone who enjoys gathering with loved ones or simply likes to add a little extra polish to their winter wardrobe. When considering a gift, think about the recipient’s favorite colors, preferred patterns, and the kinds of events they typically attend during the holidays. Plaids and rich seasonal hues are always a welcome sight this time of year, bringing a cheerful note to family photos, office parties, and end-of-year celebrations alike. For those who spend their holidays traveling, a durable, wrinkle-resistant shirt can be a real game changer—easy to pack and ready to wear straight from the suitcase. And because a great holiday dress shirt is both practical and timeless, it’s a gift that feels personal and useful, whether you’re shopping for a parent, sibling, partner, or close friend. For even more options that blend classic style with festive flair, take a look at our Holiday Shirt Dresses collection—a perfect complement to any holiday wardrobe.

As December days grow shorter and the air turns crisp, holiday dress shirts become a reliable go-to for layering warmth and style. Picture yourself heading out for a snowy stroll before dinner, your shirt peeking out from beneath a favorite sweater, or relaxing by the fire after a long day, feeling comfortable and put-together. These shirts are designed with real life in mind—easy to care for, sturdy enough to handle an impromptu snowball fight, and classic enough to look right at home at any festive gathering. The right holiday dress shirt can help you feel confident and comfortable, whether you’re hosting a houseful of guests or simply enjoying a quiet celebration with those closest to you. With so many ways to wear and share them, holiday dress shirts are a smart choice for anyone looking to add a touch of warmth and tradition to their winter season.

It's time to upgrade your browser

Holiday Dress Shirts