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.

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298 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, Traditional Fit Short-Sleeve Check
Price was from: $54.95 now: $44.99

A red check short-sleeve shirt made from wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Wrinkle-free and stays crisp Great fit and true to size Lightweight and breathable for summer Attractive color and print options Comfortable and soft fabric
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: $54.99

An arctic blue, wrinkle-free, ultrasoft brushed cotton shirt with a slightly fitted untucked fit and spread collar.

Pros: Great fit Attractive appearance Wrinkle-free Comfortable brushed cotton Beautiful color
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Price was from: $69.95 now: $54.99

A yellow cotton-blend plaid shirt with stretch, moisture-wicking performance, and a relaxed untucked fit.

Pros: Well-made and durable High quality material Stylish design Attractive color and print Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $54.99

A slightly fitted plaid oxford shirt in goldenrod, made from a moisture-wicking cotton blend with stretch.

Pros: High quality fabric Perfect fit Comfortable feel 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 Signature Premium Pima Cotton Oxford Shirt, Long-Sleeve
Price was from: $89 now: $74.99

A slim-fit oxford shirt in camp green plaid, crafted from 100% Pima cotton for luxurious softness.
Men's Wrinkle-Free Pinpoint Oxford Cloth Shirt, Traditional Fit

A wrinkle-free, 100% cotton shirt in French blue with a traditional fit and durable, non-iron fabric.

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

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 Bean's Wrinkle-Free Everyday Shirt, Traditional Untucked Fit, Plaid, Long-Sleeve
Price was from: $59.95 now: $49.99

A breathable, no-iron plaid shirt in rose wash cotton poplin, designed for untucked wear.

Pros: Wrinkle-free Comfy and durable Perfect for multiple seasons Wide size availability Bright and refreshing color
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit

A light cobalt cotton blend shirt with moisture-wicking fabric and a relaxed untucked fit for year-round comfort.

Pros: Quality fabric Versatile Good fit Dressy yet comfortable Casual style
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 Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid

A slightly fitted, moisture-wicking plaid shirt in coastal sky, made from a lightweight cotton blend.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $59.99

A green chambray shirt offering moisture-wicking comfort with a slightly fitted untucked fit and hidden features.
Men's Signature Stretch Poplin Shirt, Long-Sleeve, Slim Fit
Price was from: $79 now: $64.99

A slim fit, emerald spruce shirt made from a soft cotton blend with a button-down collar and chest pocket.

Holiday Dress Shirts

The right holiday dress shirt is more than just a piece of clothing—it’s an invitation to celebrate, connect, and make lasting memories with the people who matter most. Whether you’re gathering with family for a backyard cookout, attending a neighbor’s summer wedding, or heading out for a festive dinner with friends, a well-chosen shirt sets the tone for the occasion. This time of year calls for shirts that balance comfort and style, with breathable fabrics that feel just right on warm evenings and classic details that look sharp in every setting. Many folks appreciate shirts that move easily from afternoon to evening, looking just as good paired with chinos for a casual get-together as they do tucked in under a blazer for a more dressed-up affair. The versatility of holiday dress shirts makes them a thoughtful gift, too—something anyone would reach for again and again, season after season. It’s easy to picture a father and son, each in a crisp, comfortable shirt, sharing a laugh over the grill, or a group of friends posing for photos in shirts that feel as festive as the occasion itself.

When selecting a holiday dress shirt, it’s worth considering a few key details that can make all the difference. Look for timeless patterns and colors that complement the season—subtle plaids, gentle stripes, or classic solids that feel fresh and inviting. Breathable cottons or blends help keep things cool when the celebrations heat up, while thoughtful touches like wrinkle resistance and easy-care finishes mean you can spend less time ironing and more time enjoying the moment. Comfort is always at the forefront, with relaxed collars and soft, durable fabrics designed to keep up with every hug, toast, or impromptu dance. For those who love to give gifts that are both practical and personal, a holiday dress shirt is a reliable choice. It’s a gesture that says you care about both comfort and style, and it’s sure to be appreciated whether it’s unwrapped at a family gathering or delivered as a surprise to a friend who loves to entertain. These shirts also offer a sense of togetherness—coordinated looks for family photos, matching shirts for a group outing, or simply a favorite shirt that becomes part of someone’s holiday tradition.

From the first invitations to the last goodbyes, holiday dress shirts help create the backdrop for summer celebrations and special moments. They’re a staple that brings people together, making every gathering feel a little more memorable. If you’re looking to refresh your own collection or find a gift that’s sure to be worn with pride, our curated selection makes it easy to find just the right fit for any occasion. For more options and inspiration, explore our Holiday Shirts For Men page, where you’ll find shirts designed to help everyone feel comfortable, confident, and ready for whatever the season brings.

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Holiday Dress Shirts