Plaid Holiday Shirts

Plaid holiday shirts bring a festive touch to any wardrobe, perfect for celebrating the season in style. With a variety of colors and patterns, these shirts are designed to capture the spirit of the holidays while offering timeless appeal. Whether you're attending a family gathering or enjoying a cozy night by the fire, plaid holiday shirts provide a comfortable and versatile option that effortlessly blends tradition with modern charm.

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270 Items

Men's Scotch Plaid Flannel Shirt, Traditional Fit
Price was from: $59.95 now: $49.99

A soft, high-quality Portuguese cotton flannel shirt in authentic Scottish tartan, featuring a relaxed traditional fit.

Pros: Fits well Good quality Softness Warmth Comfortable
Men's Chamois Shirt, Traditional Fit, Plaid
Price was from: $84.95 now: $69.99

A heavy-weight, ultra-soft plaid flannel shirt in barley, perfect for layering with a relaxed traditional fit.

Pros: High quality Attractive color Softness Warmth 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 Fleece-Lined Flannel Shirt, Traditional Fit

A supersoft black plum plaid flannel shirt with cozy polyester fleece lining and a relaxed traditional fit.

Pros: Quality Comfort Warmth Softness Versatility
Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted

A slightly fitted, ultrawarm grey Stewart plaid shirt with soft Sherpa fleece lining and taffeta-lined sleeves.

Pros: Attractive design Exceptional warmth Soft and cozy feel High quality construction Comfortable fit
Women's Vacationland Seersucker Shirt, Short-Sleeve Popover Plaid
Price was from: $44.95 now: $29.99

A relaxed-fit cotton seersucker shirt in sunrise pink plaid, featuring a deep button-front placket.

Pros: Lightweight Great color Versatile Comfortable fit Breathable
Women's Wrinkle-Free Pinpoint Oxford Shirt, Long-Sleeve Relaxed Fit Plaid

An alpine blue plaid, wrinkle-free oxford shirt in 100% cotton with a relaxed fit and pearlized buttons.

Pros: High-quality material Perfect fit Wrinkle-free Versatile Comfortable
Men's Scotch Plaid Flannel Shirt, Slim Fit

A slim-fit flannel shirt in indigo tartan, made from high-quality Portuguese cotton for lasting comfort.

Pros: Perfect slim fit Durable and well-constructed Rich and attractive colors Comfortable and soft feel High-quality cotton
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $49.99

A slim-fit plaid shirt in golden cider, made from 100% cotton flannel for vintage softness.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A bayside blue plaid oxford shirt with moisture-wicking, stretchable cotton blend, designed for untucked wear.

Pros: Lovely color High quality material Stylish Comfortable Good fit
Men's Chamois Shirt, Slightly Fitted, Plaid
Price was from: $84.95 now: $69.99

A slightly fitted, extra-large apple cinnamon plaid shirt made from 7.5 oz. Portuguese cotton flannel.

Pros: Perfect fit Excellent quality Warmth Comfortable Versatility
Men's Organic Cotton Seersucker Shirt, Short-Sleeve, Slightly Fitted, Plaid
Price was from: $49.95 now: $39.99

A breathable red plaid shirt in 100% organic cotton seersucker, offering a slightly fitted silhouette.

Pros: High quality Breathable fabric Stylish design Versatile look Comfortable fit
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A slightly fitted, untucked plaid shirt in bayside blue, made from a moisture-wicking cotton blend.

Pros: High quality fabric Perfect fit Comfort Wrinkle-free after washing Untucked design
Men's 1912 Field Flannel Shirt, Slightly Fitted Untucked Fit, Plaid

A rugged blue cotton flannel shirt with a soft brushed finish and durable triple-needle stitching.

Pros: Great fit Very comfortable Exceptionally soft fabric
Men's Maine Guide Shirt

A durable, plaid field guide shirt in red and black, made from an 85% wool and 15% nylon blend.

Pros: Great fit High quality Good quality Cushioning Warm
Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft, Plaid

A plaid wool/nylon jac-shirt with PrimaLoft insulation, perfect for layering in cool or cold weather.

Pros: Very comfortable Durable construction Excellent warmth
Men's Maine Guide Zip-Front Jac-Shirt, Plaid

A rugged green and black plaid jac-shirt made of 85% wool and 15% nylon for year-round wear.

Pros: Warmth for cool weather Durable material High quality construction Good value for price Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $59.99

A red plaid chambray shirt in a breathable cotton blend with stretch and a modern untucked fit.

Pros: Great looking Attractive colors Perfect fit Receives compliments
Men's Maine Guide Lightweight Wool Field Shirt, Plaid

A durable, plaid field shirt in royal red and black, made from a soft merino wool blend.
Men's Comfort Stretch Performance® Shirt, Long-Sleeve, Slightly Fitted Untucked Fit, Plaid
Price was from: $74.95 now: $49.99

A slightly fitted, quick-drying plaid shirt in a cotton blend with moisture-wicking performance fabric.
Women's Maine Guide Zip Front Jac-Shirt with Primaloft, Plaid

A deep red plaid wool blend jac-shirt with PrimaLoft insulation, perfect for layering in cold weather.
Men's Brushed Jaspé Twill Shirt, Plaid, Traditional Untucked Fit

A lightweight, apple cinnamon plaid shirt made from 100% cotton with a relaxed untucked fit.
Men's Maine Guide Lightweight Lined Wool Field Shirt, Plaid

A red wool-blend plaid shirt with grid fleece lining for extra warmth and classic outdoor style.
Men's Scotch Plaid Flannel Shirt, Snap-Front, Slightly Fitted Untucked Fit

A green Portuguese cotton flannel shirt with snap-front, corduroy trim, and authentic yarn-dyed tartan.

Plaid Holiday Shirts

There’s something unmistakably inviting about a plaid shirt, especially as the holiday season draws near and cooler days call for layers that feel as good as they look. Plaid holiday shirts have a way of bringing people together, whether it’s around a crackling fire, gathered at the dinner table, or out for a walk in the crisp winter air. The classic patterns and vibrant colors instantly evoke a sense of warmth, comfort, and celebration. For many, pulling on a soft plaid shirt is a tradition in itself—one that signals the start of festive gatherings, cookie-baking afternoons, and tree-trimming evenings. These shirts are designed for lasting value, crafted from durable materials that hold up to years of wear, wash after wash. They’re as at home layered over a favorite tee as they are tucked in for a more polished look, making them a versatile choice for everything from casual family get-togethers to outdoor adventures like tree hunting or sledding with the kids.

When choosing a plaid holiday shirt, it helps to consider who will be wearing it and how it will be used. Families often appreciate shirts that come in a range of sizes and styles, making it easy to coordinate for holiday photos or simply enjoy a sense of togetherness during the season. These shirts make thoughtful gifts for just about anyone—parents, siblings, friends, even coworkers—since their timeless patterns and easy-going comfort suit a wide range of tastes and occasions. For those who spend a lot of time outdoors, a plaid shirt can be a reliable companion, offering just the right amount of warmth and breathability for layering under a vest or over a thermal. And for moments spent indoors, the soft, brushed fabric and relaxed fit make it easy to unwind and enjoy the simple pleasures of the season. Plaid shirts are not just for the holidays, either; their enduring style and durability mean they’ll become a favorite for chilly mornings, autumn hikes, or even cool summer nights around the campfire. For anyone looking to expand their collection, or perhaps try a new style, our Plaid Pullovers offer another cozy and practical option that’s just right for layering.

The appeal of plaid holiday shirts goes beyond their good looks—they’re built to solve real problems, like finding a layer that’s both comfortable and easy to care for, or choosing a gift that feels personal and practical. The best ones offer thoughtful details like sturdy buttons, reinforced seams, and easy-to-roll sleeves, all designed to stand up to the demands of busy days and spontaneous adventures. It’s the kind of shirt you can reach for year after year, knowing it will always feel just right, whether you’re heading out to cut your own tree, wrapping gifts by the fire, or simply savoring a quiet moment with a mug of cocoa. With so many colors and patterns to choose from, it’s easy to find a plaid that matches your own sense of style or brings a little extra cheer to someone else’s holiday season. And because these shirts are made to last, they carry memories from one season to the next, becoming a beloved part of your winter wardrobe and holiday traditions.

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Plaid Holiday Shirts