Cool Weather Shirts

When the temperatures start to drop, staying comfortable and cozy becomes a top priority. Our collection of cool weather shirts offers the perfect blend of style and functionality, ensuring you stay warm without sacrificing your look. From casual outings to outdoor adventures, these shirts are designed to keep you feeling great in any setting. With a variety of styles, colors, and patterns to choose from, finding your new favorite shirt has never been easier. Embrace the chill with confidence and enjoy every moment outside with our versatile selection of cool weather shirts.

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476 Items

Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve

A navy blue, long-sleeve tee made of 100% cotton that resists shrinking, fading, and pilling.

Pros: Durable and well-made Variety of colors Maintains shape and color High-quality fabric Comfortable fit
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A deep sapphire multi houndstooth flannel shirt offering superior softness, warmth, and resistance to shrinking and wrinkling.

Pros: Great quality Warmth Excellent fit Comfortable Superior softness
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit

A soft spruce cotton tee that resists wrinkles, shrinking, fading, and pilling, with a comfortable traditional fit.

Pros: High quality Durable construction Color retention Soft fabric Comfortable fit
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley

A resilient gray heather henley made from 100% cotton that resists shrinking, fading, and pilling.

Pros: Great fit High quality Versatile Comfortable Soft fabric
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check

A wrinkle-free blue check shirt made from 100% cotton poplin with moisture-wicking TrueCool® fabric.

Pros: High quality Wrinkle-free Lightweight Good fit Comfortable
Men's Carefree Unshrinkable Tee, Traditional Fit, Henley

A charcoal heather Henley made from 100% jersey-knit cotton, resisting wrinkles, shrinking, fading, and pilling.

Pros: Easy care Perfect fit Durable fabric Versatile design True to size
Men's Airlight Knit Pullover

A quilted synthetic fleece pullover in balsam that wicks moisture, dries quickly, and offers UPF 50+ protection.

Pros: Lightweight Warmth Versatile Comfortable Good fit
Men's Katahdin Iron Works® Bonded Waffle Fleece Henley

A mariner blue Henley with ultrasoft, pill-resistant waffle-knit fabric and plush berber fleece lining.

Pros: High quality True to size fit Warmth Softness Comfortable
Women's Pima Cotton Tee, Shawl Long-Sleeve

A luxurious black long-sleeve tee made from 100% American-grown Supima® cotton with a flattering shawl collar.

Pros: High quality Flattering fit Versatile style Soft fabric Comfortable to wear
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $49.99

A slim-fitting, 100% cotton flannel shirt in darkest indigo stripe, offering vintage comfort and style.

Pros: Beautiful design High quality Warmth Soft fabric Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

A green cotton blend shirt with built-in stretch, perfect for untucked wear and easy movement.

Pros: Great fit High quality Versatile design Excellent comfort Soft fabric
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit

A slim-fit indigo heather flannel shirt made from 100% cotton for ultimate softness and comfort.

Pros: Perfect fit Quality Comfort Softness Style
Men's Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $54.99

A light gray heather, slim-fit flannel shirt made of midweight 100% cotton for extra softness and durability.

Pros: High quality Perfect fit Lighter weight True to size Versatile
Men's Signature Waffle Crew

A slim-fitting thermal crew made of breathable, 100% waffle-knit cotton in oyster shell color.

Pros: High quality Great color Good fit Comfortable waffle knit Excellent warmth
Men's Cresta Midweight 250 Quarter-Zip Top

A midweight merino wool quarter-zip top in carbon navy, designed to wick sweat and resist odor.

Pros: Keeps you warm Excellent base layer Comfort Durability Versatility
Men's Maine Guide Shirt

A durable, 85% wool and 15% nylon plaid shirt, perfect for layering, available in cobalt and black.

Pros: Great fit High quality Good quality Stylish 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: Comfort Warmth Durability
Men's No Fly Zone Shirt, Long-Sleeve
Price was from: $99 now: $84.99

A dark amber, long-sleeve shirt that repels insects, offers UPF 50+ protection, and features moisture-wicking fabric.
Men's Katahdin Performance Flannel Shirt-Jacket, Hi-Pile Fleece-Lined Plaid
Price was from: $130 now: $49.99

A durable, quick-drying flannel shirt-jacket with hi-pile fleece lining, available in eucalyptus and deep admiral blue.

Pros: High quality Perfect fit Great warmth Stylish appearance Soft fabric
Men's Maine Guide Zip-Front Jac-Shirt, Plaid

A rugged wool/nylon jac-shirt in green and black plaid, perfect for layering and outdoor activities.

Pros: Great fit High quality Warmth Durable Comfortable fabric
Men's Signature Waffle Henley
Price was from: $99 now: $59.99

A slim fit, breathable waffle-knit cotton henley in light saddle, perfect for layering in cooler weather.

Pros: Beautiful design Unmatched quality True to size Warm and comfortable Versatile and well-made
Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft

A warm, windproof wool/nylon jac-shirt with PrimaLoft Silver lining, ideal for layering in cold weather.

Pros: Very warm Good fit Comfortable to wear
Women's Maine Guide Zip Front Jac-Shirt with Primaloft

A loden wool blend jac-shirt with PrimaLoft insulation, featuring multiple pockets and a rugged brass zipper.

Pros: Great fit High quality Non-itchy material Excellent warmth
Men's Signature Donegal Woven Shirt, Long-Sleeve

A rugged cream twill flannel shirt with Donegal flecks, slim fit, and button-down collar.

Cool Weather Shirts

As the days grow shorter and the air takes on a refreshing chill, the right cool weather shirt becomes an essential part of your everyday routine—whether you’re heading out for a brisk morning walk, gathering around the backyard firepit with friends, or simply relaxing with family at home. Cool weather shirts are designed to offer just the right amount of warmth and comfort, making them a staple for anyone who enjoys spending time outdoors or appreciates that extra layer of coziness indoors. These shirts are crafted from quality materials chosen for their durability and soft feel, so you can count on them to hold up season after season, through everything from raking leaves to impromptu hikes. The thoughtful details—like easy-to-roll sleeves, classic colors, and relaxed silhouettes—make it simple to transition from outdoor adventures to casual dinners without missing a beat.

With so many styles and features to choose from, finding the perfect cool weather shirt is all about considering when and how you’ll wear it. Some folks reach for a flannel shirt for its timeless appeal and reliable warmth, while others prefer a lightweight layer that’s easy to slip on over a favorite tee. Families often stock up on a variety of options to have everyone ready for school drop-offs, weekend getaways, or those spontaneous leaf-pile-jumping sessions in the backyard. Cool weather shirts also make thoughtful gifts—there’s something special about giving a loved one a shirt that’s built to last and ready for whatever the day brings, from tailgates to trail walks. And because these shirts are designed with comfort and versatility in mind, they’re just as at home layered under a vest for a weekend hike as they are dressed up with a scarf for a cozy dinner out.

No matter your plans this season, a well-made cool weather shirt is a reliable companion—easy to care for, always comfortable, and suited to a wide range of activities and settings. They’re a go-to for anyone who values lasting quality and timeless style, whether you’re updating your own closet or searching for a practical, appreciated gift. And when the forecast finally calls for warmer days again, you’ll find plenty of options for every season—including our collection of Shirts For Hot Weather—so you’re always prepared for whatever the weather brings.

FAQs

Cool weather shirts are often crafted from materials like brushed cotton, flannel, heavyweight jersey, and thermal blends. These fabrics are chosen for their ability to provide warmth, breathability, and lasting durability, making them ideal for layering or wearing on their own during chilly days.

Absolutely. Cool weather shirts are designed with versatility in mind, making them perfect for layering over tees or under sweaters, vests, and jackets. This allows you to easily adjust your comfort level as temperatures change throughout the day.

Most cool weather shirts are easy to care for—simply machine wash with like colors and tumble dry on low. For best results, check the care label for specific instructions and avoid using harsh detergents or bleach, which can break down fibers over time.

Cool weather shirts make a thoughtful and practical gift for just about anyone, whether they enjoy outdoor adventures, cozy evenings at home, or simply appreciate comfortable, durable clothing. Their timeless style and lasting quality ensure they’ll be appreciated for seasons to come.

Yes, cool weather shirts are designed to be versatile enough for a wide range of activities. They’re great for outdoor pursuits like hiking or apple picking, but are just as comfortable for indoor gatherings, family meals, or relaxing at home.

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Cool Weather Shirts