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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298 Items

Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve
Men's Carefree Unshrinkable Tee with Pocket, Traditional Fit
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley
Men's Wrinkle-Free Kennebunk Sport Shirt, Traditional Fit Check
Men's Carefree Unshrinkable Tee, Traditional Fit, Henley
Men's Flannel-Lined Hurricane Shirt
Price was from: $89 now: $74.99
Men's Katahdin Fleece Pullover
Price was from: $69.95 now: $54.99
Men's Airlight Knit Pullover
Men's Katahdin Iron Works® Bonded Waffle Fleece Henley
Women's Pima Cotton Tee, Shawl Long-Sleeve
Women's Vacationland Seersucker Shirt, Long-Sleeve Plaid
Women's Vacationland Seersucker Shirt, Long-Sleeve
Men's BeanFlex® All-Season Flannel Shirt, Traditional Untucked Fit, Long-Sleeve
Price was from: $64.95 now: $49.99
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check
Price was from: $64.95 now: $54.99
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit, Pattern
Price was from: $89 now: $69.99
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve, Print
Price was from: $69.95 now: $59.99
Men's Wrinkle-Free Ultrasoft Brushed Cotton Shirt, Long-Sleeve, Slightly Fitted Untucked Fit
Price was from: $69.95 now: $54.99
Men's Comfort Stretch® Oxford Shirt, Traditional Untucked Fit, Plaid
Price was from: $69.95 now: $54.99
Men's Signature 1933 Chamois Cloth Shirt, Slim Fit
Men's BeanBuilt Waffle Henley, Traditional Untucked Fit
Price was from: $64.95 now: $54.99
Women's L.L. Bean Heritage Washed Denim Shirt, Lined
Price was from: $89 now: $79.99
Men's Comfort Stretch® Oxford Shirt, Slightly Fitted Untucked Fit, Plaid
Price was from: $69.95 now: $54.99
Men's Signature Heritage Textured Flannel Shirt
Price was from: $79 now: $64.99

Cool Weather Shirts

As the leaves start to turn and the air grows crisp, the transition from summer to cooler weather calls for a wardrobe update that keeps you comfortable, warm, and ready for any outdoor adventure or cozy indoor gathering. Cool weather shirts are a staple in this seasonal shift, providing not just warmth but also a dash of style to your daily outfits. Whether you're planning a weekend hike through the vibrant autumn foliage, a casual meet-up with friends around a fire pit, or simply need a reliable layer for your daily commute, the right shirt can make all the difference in elevating your comfort and style.

Cool weather shirts come in a variety of materials and designs, each suited to different needs and preferences. For those who spend time outdoors, shirts made from flannel or heavyweight cotton offer superb warmth and durability. These materials are not only soft against the skin but also stand up well against the chilly winds of autumn. On days that are sunny yet brisk, a lighter cotton or a blend that includes a bit of stretch provides comfort without overheating. It’s the perfect choice for those who transition between the cool outdoors and heated indoors throughout the day. For added convenience, many of these shirts feature pockets that are practical for carrying small essentials, making them as functional as they are fashionable.

Gift-giving during the cooler months often includes these practical yet stylish shirts, as they are appreciated for their versatility and comfort. A well-chosen cool weather shirt can be a thoughtful present for anyone who appreciates outdoor activities or who simply values a well-rounded wardrobe that's prepared for any weather. As we look ahead to warmer days, it’s also wise to prepare for the seasonal wardrobe shift. For those lighter, breezier shirts perfect for sunnier times, be sure to check out our collection of Shirts For Hot Weather. Just as our cooler weather options ensure warmth and style, our warmer weather shirts offer comfort and ease, making transitions between the seasons seamless and enjoyable. Whether layering up for a chilly morning or dressing down for a warm afternoon, having the right shirt for the right weather is all about embracing the moment while being comfortably you.

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Cool Weather Shirts