The 20 Best Men’s Flannel Shirts For Winter
While there are certain shirts that can be worn year-round, there’s no shirt that exemplifies rugged fall and winter style quite like the perfect flannel shirt. The best men’s flannel shirts harken back to the hearty, outdoor-oriented nature of this tough, yet comfortable fabric. And yet, brands are finding newer and better ways to update them for today’s modern guy.
Whether you find yourself squarely in the outdoors set or are more inclined to stroll to Sunday brunch, there’s definitely a place — or several — in your wardrobe for the flannel shirt. And you’ve got plenty of brands and options to pick from, as heritage brands are making flannels right alongside more familiar menswear labels. The durability and versatility of a flannel shirt is such that you can layer it over a henley or thermal shirt, you can style it atop — or beneath — a slim crewneck sweater, and you can certainly wear it on its own. The rest of the time, you should wear it exactly how you please — the best men’s flannel shirts can handle anything you throw at ‘em.
Outerknown Transitional Flannel Shirt
The Outerknown Transitional Flannel Shirt is just what you want for that time of year when the weather just can’t seem to make its mind. On those unpredictable days, this lightweight, ultra-soft flannel shirt will keep you cool during the hot hours and warm in the cooler mornings and evenings.
The material is smooth and gentle against even the most sensitive skin, and won’t rub even when you heat up. It’s made from a sustainable organic cotton and a natural plastic alternative (tagua palm nuts), so it’s as eco-friendly as it is handsome and comfortable.
Price: $138
Schott Plaid Cotton Flannel Shirt
Stand out from the crowd in Schott’s Plaid Cotton Flannel Shirt. Made with the same rebellious style that brought their OG motorcycle jacket into the pinnacle of fashion in the early 1900s, this plaid flannel features bold colors, eye-catching patterns, and a classic cut that pairs well with your weekday and weekend outfits.
The midweight construction makes it light enough to wear as a layer beneath a jacket or coat, but thick enough to wear alone during early fall and late spring. You’ll be amazed at just how efficiently the brushed cotton flannel traps in body heat during those chillier hours.
Price: $80
Taylor Stitch Ledge Shirt
Taylor Stitch delivers maximum comfort, reliability, and craftsmanship in their Ledge Shirt. From their reinforced lock-stitched buttons and buttonholes to the double needle-felted construction, it’s a shirt built to last. But it also looks handsome, thanks to its signature California collar, classic silhouette, shorter hem, and unique charcoal buttons.
Wear it untucked over a pair of your favorite light-colors slacks to dress it up, or over dark-colored jeans for a more casual look. Wear it day in and day out and trust the colors won’t fade, the fabric won’t sag, and the shirt will always make you look your absolute handsomest.
Price: $110
Fair Harbor Ultra-Stretch Dunewood Flannel
You’ve never felt soft quite like Fair Harbor flannel. The fabric used for the Ultra-Stretch Dunewood Flannel is smooth and silky as a cloud against your skin, but thanks to the addition of synthetic fibers, it’s also highly versatile. It stretches and flexes with your body and is naturally breathable so you stay cool and comfy when the days turn hot.
The heritage plaids deliver an upscale variation on the classic flannel, and the relaxed modern fit is sure to keep you comfortable all day long.
Price: $98
Flint and Tinder Jackson Flannel Shirt
Looking for a way to dress up while still wearing flannel? Give the Flint and Tinder Jackson Flannel Shirt a try. This bad boy is made with all the warmth, softness, and comfort that has you reaching for flannel during the cooler months, but the dark colorways and classic fit give it a touch of elegance that makes it suitable for a date night or day out on the town.
The midweight construction strikes just the right balance of thickness, making it warm but still nicely versatile. And because it’s just so velvety soft, it’s a shirt you’ll be glad to wear all winter long.
Price: $118
Filson Flannel Service Shirt
The Filson Flannel Service Shirt takes everything you appreciate about bold military colors and patterns and pairs them with a truly comfortable, easy-wearing design. The long-sleeved shirt is made with a mid-weight cotton that will hold up against those autumn winds and spring showers and serves as an excellent midlayer during the dead of winter.
The slub finish gives it a wonderfully soft texture that won’t rub or irritate your skin even if you’re sweating, chopping wood, or heading out for a hike. Thanks to the dual rear pleats, you’ve got extra freedom of movement no matter how broad your shoulders. Between the bold color choices, classic style, and activity-friendly construction, it’s a shirt you’ll be glad to add to your wardrobe.
Price: $125
Billy Reid Flannel Bold Plaid Tuscumbia Shirt
Show off just how audacious your style choices are with the Billy Reid Flannel Bold Plaid Tuscumbia Shirt. Details like the bright colors, bold plaid patterns, bias spade chest pocket, and genuine mother-of-pearl buttons elevate this a cut above basic flannel, and the standard fit ensures it hugs your torso comfortably while still accentuating your masculine physique.
Right out of the box, it has a wonderful lived-in feel that will instantly make it your favorite shirt. The more you wear it, the more “you” it will become.
Price: $248 $173
Bonobos Fireside Flannel Shirt
For those cool nights camping, hiking, or backyard BBQing, the Bonobos Fireside Flannel Shirt will be your shirt of choice. It’s built for cold weather activity, with a midweight construction and just enough stretch you’ll be comfortable whether you’re swinging an axe, a walking stick, or a ski pole.
The double chest pockets offer plenty of storage space for your EDC essentials. Available in both slim and standard fits, you can find the shirt that suits your body shape best.
Price: $110
Stio Miter Lightweight Flannel Shirt
Stay cool and comfy in the Stio Miter Lightweight Flannel Shirt. This shirt is built for guys who want to wear flannel all year around, and who like the relaxed vibe of a long-sleeved shirt over a crisp white tee with jeans and boots. The fabric is light enough you’ll barely feel it but has the toughness to hold up to your woodworking, farming, or hunting.
The double-brushed cotton is soft and silky against your skin. You’ll love how the forward-facing shoulder seams maximize the mobility of your arms. Really, it’s a shirt you can wear anywhere, anytime, and know you’ll look and feel like the rugged mountain man you are.
Price: $115
Relwen Chamois Lined Flannel Shirt
This Relwen shirt is so much more than just your basic flannel; it’s also lined with a velvety chamois that feels wonderful against your skin while also adding an extra layer of warmth. It’s the ideal cool-weather shirt that you can wear all winter long beneath your favorite jacket or parka.
Pair it with your favorite jeans for a day out on the town, or a pair of sweatpants for lounging around your house. The soft, warm fabric is as comfortable indoors as it is outdoors.
Price: $188
Outerknown Blanket Shirt
You show us a brand making one of the best flannel shirts on the market, and we’ll tell you all about a brand we love. Let us know about a brand that makes flannel shirts while doing so sustainably, and you can color us very, very impressed indeed. Such is the case with Outerknown, the surf-inspired brand launched in part by ocean legend Kelly Slater.
Pieces like the Outerknown Blanket Shirt bring the brand far beyond the beach and into your regular fall style rotation, easily.
Faherty Legend Sweater Shirt
Comfort-focused flannels tend to pile on the thickness, which is cozy, but often as restricting as the snow outfit Ralphie’s brother wore in A Christmas Story. The Faherty Legend Sweater Shirt is outrageously cushy thanks to the lightweight and luxurious viscose in its weave, but also provides all of the mobility, thanks to its stretchy elastane and clever fit. The body and sleeves are relaxed at the top, which gives you all the room you need to move, but then taper slightly, ensuring the flexible material moves with you as well. Plus, this sweater shirt comes in some vivid color combos, accommodating a wide range of personal styles.
California Cowboy High Sierra Shirt
A modern twist on the quintessential flannel, California Cowboy makes some thrilling choices with the High Sierra Shirt, starting with a clever slim fit. This adds a touch of youthfulness without overdoing it since it’s a moderate slim cut, far from skinny. Portuguese flannel, with which this shirt is made, is known for its soft, strong, and pill-resistant build thanks to its luxurious long-staple cotton.
Also, the colorways range from a distinct but neutral black with yellow accents to a spring mix of primary shades. If you’re going to look this great, you have to be prepared to attract attention and do some socializing; all of the shirts come with a stack of conversation cards, plus a beer koozie and bottle opener.
Mack Weldon WARMKNIT Flannel Shirt
With colorways and patterns like calmly-hued tattersalls and subtly heathered gray, the Mack Weldon WARMKNIT Flannel Shirt has the tiniest bit of formality to it that would partner harmoniously with chinos. The soft brush finish is almost velveteen. No worries though, as this clean-lined style doesn’t compromise the comfort factor, especially with the relaxed drape and ThermoLite insulation.
ThermoLite offers real insulation, minus the bulk, and releases moisture too. After all, you want your flannel to keep you warm, not make you sweat.
Kuhl Fugitive Flannel
A skosh smoother than your typically super-napped flannel, the Kuhl Fugitive also brings all-day comfort and some premium accents.
The metal buttons, for example, add subtle shine under certain lights but also provide durability and ease-of-use. Meanwhile, the midweight plaid body is woven in with a magical ingredient called Tencel, which makes the shirt breathable, stretchy, and highly absorbent. It’s the same material used in sheets made for hot sleepers, but works just as well when you’re awake.
Patagonia Fjord Flannel Shirt
The Patagonia Fjord Flannel Shirt is a menswear essential, encapsulating the easy style of the outdoorsy, every cool dad ever, and the tool shed set. While the aesthetic is stylishly neutral, even if you’re going for one of their brighter colorways (like the lively orange), the build is sophisticated. This shirt is made of 100% in-conversion cotton.
This combines lightness in weight with long-lasting endurance, while also being eco-forward. The process of making it improves soil and reduces toxic output.
Filson Alaskan Guide Shirt
The Filson Alaskan Guide Shirt has that tradesmen-cool aesthetic that never goes out of style, and that all guys look great in. It’s actually a go-to flannel for genuine sportsmen, ranchers, and other OG flannel wearers. The twill is tightly-woven from brushed cotton, which ensures effective warmth and durability.
Meanwhile, the pleated shoulders make it easy for you to make big movements, in case you need to lasso a horse. Moreover, the relaxed fit mercifully suits and flatters a wide range of body types.
L.L. Bean Men’s Scotch Plaid Flannel Shirt
Tap into your Scottish heritage and wear the tartan colors proudly with the L.L. Bean Men’s Scotch Plaid Flannel Shirt. Made from the same fabric as Scottish tartans, this flannel shirt is silky smooth on your skin but still holds up to heavy sweating, hiking, or working.
The flannel fabric is woven together with longer-staple cotton to enhance both durability and comfort. With its bold colors and patterns, it will immediately stand out from every other flannel shirt around you.
The Perfect Flannel Shirt
When we want uncompromising outdoor gear with strong heritage and extremely high quality, we look toward Orvis — and that’s perhaps why we were so drawn to the Orvis Perfect Flannel Shirt (hey, we said flannel is the “perfect fall shirt,” did we not?).
The cotton flannel in question here is available in a stylish array of classic colors, all the better for mixing and matching with rugged chore pants or faded blue denim alike. And the double-brushed fabric treatment only makes this flannel shirt even more likely to be one of the best flannel shirts you’ll own.
L.L. Bean Fleece-Lined Flannel Shirt
L.L. Bean is likely one of the first brands that pops to mind when you think of classic, New England-style pieces. That ethos starts with the brand’s lauded “Duck Boots,” and it carries just as much weight when it comes to warm, easily layered pieces like its Fleece-Lined Flannel Shirt.
Made with garment-dyed and brushed flannel for extra comfort, this classic shirt is going to feel right at home this holiday season and into the cold winter, especially with a plethora of color options and a reliably affordable price point.
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