Mens Winter Long Sleeve Shirts

Gear up for the colder months with our collection of men's winter long sleeve shirts, crafted to keep you warm and comfortable no matter the chill in the air. Whether you're layering up for a brisk morning hike or enjoying a casual evening by the fire, these shirts offer timeless style that seamlessly blends with your outdoor adventures. Designed with versatility in mind, our selection caters to every taste, ensuring you find the perfect fit for both rugged pursuits and relaxed outings. Embrace the season with confidence, knowing each piece is built to last and ready to accompany you on countless winter escapades.

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Men's Chamois Shirt, Traditional Fit

A heavy-weight, charcoal gray heather flannel shirt made from 7.5 oz. Portuguese cotton for exceptional warmth.

Pros: Nice colors Great quality Exceptional warmth Durable material Comfortable fit
Men's Two-Layer River Driver's Shirt®, Traditional Fit Henley

A traditional fit Henley with a wool blend outer layer and soft cotton inner, in black cherry heather.

Pros: Good quality Warmth True to size Comfortable fit Versatility
Men's Sherpa-Lined Scotch Plaid Shirt, Slightly Fitted

A slightly fitted indigo tartan shirt combining soft Portuguese flannel and warm Sherpa fleece lining.

Pros: True fit Well-made Comfort Warmth Versatility
Men's Wrinkle-Free Kennebunk Sport Shirt, Slightly Fitted Check

A deep green, slightly fitted check shirt made from 100% wrinkle-free cotton poplin with moisture-wicking TrueCool® fabric.

Pros: Attractive color High-quality construction Wrinkle-free fabric Comfortable fit No ironing needed
Men's Scotch Plaid Flannel Shirt, Traditional Fit

A soft, 100% Portuguese cotton flannel shirt in authentic Scottish tartan with a relaxed traditional fit.

Pros: Fits well Good quality Softness Warmth Comfortable
Men's Wicked Good Flannel Shirt, Traditional Fit, Houndstooth

A deep evergreen houndstooth flannel shirt with sheepskin shearling lining, offering warmth and wrinkle resistance.

Pros: Beautiful design Softness Warmth Durable Comfortable fit
Men's Scotch Plaid Flannel Shirt, Slightly Fitted

A slightly fitted flannel shirt in authentic Scottish tartan, made from high-quality Portuguese cotton.

Pros: Quality construction Perfect fit Softness Warmth Vibrant colors
Men's Unshrinkable Mini-Waffle Henley, Long-Sleeve Traditional Fit

An indigo heather, 100% cotton henley that resists shrinking, fading, and pilling, with a relaxed fit.

Pros: High quality True to size Comfortable Warm Good value
Men's Fleece-Lined Flannel Shirt, Traditional Fit

A supercozy, fleece-lined flannel shirt in coal plaid, featuring a relaxed traditional fit and multiple pockets.

Pros: Quality Comfort Warmth Softness Versatility
Men's Wicked Good Flannel Shirt, Slightly Fitted, Houndstooth

A slightly fitted charcoal heather flannel shirt with sheepskin shearling lining that resists fading, pilling, and wrinkling.

Pros: Fits well High material quality Soft and comfortable Durable construction Warm and well-vented
Men's Cresta Wool Midweight 250 Crew Top

A dark black merino wool crew top that wicks sweat, resists odor, and features thumbhole cuffs.

Pros: Great fit Comfortable feel Durable material Soft fabric Excellent warmth
Men's Maine Guide Shirt with PrimaLoft

A warm PrimaLoft wool blend shirt in cobalt and black check, perfect for layering and outdoor activities.

Pros: Great fit Excellent quality Warm and comfortable Durable material Stylish appearance
Men's Maine Guide Zip-Front Jac-Shirt, Plaid

A rugged red and black plaid jac-shirt made from 85% wool and 15% nylon, perfect for layering.

Pros: Great fit High quality Warmth Durable Comfortable fabric
Men's Maine Guide Zip-Front Jac-Shirt with PrimaLoft

A warm, windproof wool-blend jac-shirt with PrimaLoft Silver lining, ideal for hunting and layering.

Pros: Very warm Good fit Comfortable to wear
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 Signature Donegal Woven Shirt, Long-Sleeve
Price was from: $79 now: $54.99

A ruggedly handsome slim-fit shirt in canyon khaki, made from 100% cotton twill flannel with Donegal flecks.
Men's Maine Guide Sherpa Lined Wool Shirt

A luxuriously cozy wool-blend shirt with sherpa fleece lining, perfect for layering in cold weather.
Men's Maine Guide Wool Field Shirt

A navy wool blend field shirt offering unbeatable warmth, durability, and a slightly fitted design.
Men's Carefree Unshrinkable Tee, Traditional Fit, Long-Sleeve Henley

A black, long-sleeve Henley made of 100% cotton that resists wrinkles, shrinking, fading, and pilling.

Pros: Great fit High quality Versatile Comfortable Soft fabric
Men's Carefree Unshrinkable Mockneck Shirt

A soft, white cotton mockneck shirt that resists shrinking, fading, wrinkling, and pilling.

Pros: Perfect fit Excellent quality Durability Versatile Comfortable
Men's Carefree Unshrinkable Turtleneck

A charcoal heather turtleneck made from 100% jersey-knit cotton that resists shrinking, fading, and wrinkling.

Pros: High quality Comfort Warmth Fits well after wash Classic design
Men's Organic Cotton Waffle Sweater, Quarter Zip

A cozy tan quarter-zip sweater made from 100% organic cotton with a thick waffle-stitch knit.

Pros: Beautiful design High quality Warm and cozy True to size Comfortable fit
Men's Comfort Stretch® Chambray Shirt, Traditional Untucked Fit, Long-Sleeve

An indigo long-sleeve chambray shirt with built-in stretch, perfect for wearing untucked.

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

A brown cotton blend shirt with stretch, featuring a relaxed fit and moisture-wicking properties.

Pros: High quality material Easy to iron True to size Good stretch Comfortable fit

Mens Winter Long Sleeve Shirts

When winter settles in and the days grow shorter, a dependable long sleeve shirt becomes an everyday essential for men who appreciate warmth, comfort, and versatility. Whether you’re heading out for a brisk morning walk, tackling chores around the neighborhood, or simply relaxing by the fire after a day outdoors, the right long sleeve shirt makes all the difference. These shirts are designed to offer lasting value, crafted from durable materials that stand up to repeated wear and frequent washing. Their timeless styles ensure they fit seamlessly into any wardrobe, pairing easily with everything from jeans and work pants to fleece vests and insulated jackets. Many men reach for these shirts as a reliable first layer, enjoying the soft feel against their skin and the easy, unrestricted movement that comes from thoughtful construction. With options ranging from lightweight cotton to heavier flannels, there’s a long sleeve shirt for every cold-weather adventure—whether that’s shoveling the driveway, gathering around a backyard fire pit, or enjoying a weekend at a cozy cabin.

Long sleeve shirts also make practical and thoughtful gifts, especially as the holiday season approaches. They’re a welcome surprise for anyone who values comfort and quality—fathers, brothers, sons, friends, or colleagues. Because they’re so versatile, these shirts are just as suitable for a casual day at the office as they are for a weekend hike or an afternoon spent splitting firewood. The details matter: reinforced stitching, easy-to-use buttons, and classic colors or patterns that never go out of style. Many men appreciate shirts that offer a bit of extra coverage on chilly days, with sleeves that keep the cold at bay and collars that can be turned up against the wind. The right long sleeve shirt becomes a favorite piece, one that’s reached for again and again as temperatures dip. If you’re looking to refresh your own cold-weather wardrobe or searching for a gift that’s sure to be appreciated, explore the full collection of Men's Long Sleeve Shirts for options that deliver on comfort, durability, and timeless appeal.