Labor Day weekend comes and goes and all of a sudden, a cool breeze rolls in. You start wearing socks again. Your morning coffee order switches from iced coffee to hot coffee. You start drinking whiskey and bourbon instead of vodka and gin. Yep—it’s Fall, and you need to start dressing like it.
The flannel shirt has been a Fall weather staple for hundreds of years, but it’s also gone through a million different lives over the years. It went from being a badass mountain man shirt worn by the likes of Paul Bunyan to being the quintessential dad shirt. Then, the likes of Kurt Cobain and Eddie Vedder and the rest of the ‘90s grunge scene co-opted flannel and for awhile, it seemed hopelessly ‘90s to be donning anything flannel.
Not anymore. Flannel shirts are back and you’re not going to run the risk of looking like Al Borland from Home Improvement if you wear one. They’re classic, they’ll keep you warm, and they’ll make you look beyond perfect tromping through the fall foliage with your wife or sitting around a campfire with your buddies. Check out 18 of our favorites.
Uniqlo Checked Flannel Shirt
Japanese brand Uniqlo has been around since the late 1940s, but has only been available in the US since 2005. We’re glad they finally came stateside, though, because their commitment to creating affordable wardrobe staples is awesome. For just $30, you can buy up a rainbow of quality flannel shirts in the classic buffalo plaid checked pattern without breaking the bank.
J. Crew Slim One-Pocket Shirt
If you’re trying to ease yourself into the flannel game, try a solid shirt, like this one from J. Crew. You can work yourself up to the patterns.
Lands’ End Flagship Flannel
Lands’ End knows what it’s doing when it comes to flannel, so you can’t go wrong with the Flagship Flannel shirt they have on offer. More structured than other flannel shirts you’ll find on the market, this shirt has a bit more weight to it (which is good for extra chilly days), and because of the oxford button-down collar, you’ll be able to get away with wearing it to the office.
Stapleford Buffalo Plaid Flannel
Buffalo plaid refers to large checks—typically in red and black—like the kind you’d see Paul Bunyan wearing. Pair this one—made by Stapleford and available in the classic red and black combination as well as gray and white and teal and navy—with a pair of dark jeans, work boots, and maybe an axe, if you’ve got one.
LL Bean Castine Flannel
This Maine-based heritage brand knows a thing or two about creating classic pieces that stand up to the test of time, and this Castine Flannel is no exception. It’s the slimmest and lightest flannel the brand has on offer, which is good if you’re planning on wearing it to the bar instead of out in the woods.
Howler Brothers Harkers Flannel
Texas-based Howler Brothers takes its name from the Howler monkey, the loudest animal in North America. But this shirt isn’t nearly as loud as its namesake, and that’s a good thing. Classic and understated, it’s a shirt that you’ll be able to wear for years to come. Available in a variety of different color combinations, it has features like a single-button flap pocket on the chest, reinforced elbow patches, and custom metal buttons.
Patagonia Fjord Flannel
Patagonia has been a trusted name in outdoor gear for years, and while they’re known for their rugged bags and outerwear, they do make some quality apparel that you can wear indoors, like this Fjord Flannel. Made from heavyweight 100% organic cotton (and available in a variety of color combinations), this is a shirt that will keep you warm as the cold rolls in. With sturdy buttons, two deep buttoned pockets on the chest, it’s roomy enough to wear as a jacket over a t-shirt or another long-sleeved shirt.
Pendleton Elbow Patch Trail Shirt
With roots stretching back all the way to the 1800s, Pendleton is a true American heritage brand that specializes in crafting products out of quality fabrics and textiles. This Elbow Patch Trail Shirt proves that—crafted out of sturdy but soft Umatilla wool (with suede elbow patches for extra flair), Pendleton has been crafting this kind of shirt for over 80 years. Available in a variety of colors and patterns, we bet you can’t buy just one.
Pendleton Board Shirt
Another offering from Pendleton, this one is also available in a variety of colors and patterns (sixty of ‘em!). It’s a bit lighter than other offerings and is named for the surfers that would throw this shirt on to protect themselves from the ocean breeze that rolls in after a long day of surfing.
Filson Flannel Hunting Shirt
Filson has been creating quality outdoor gear since the 1800s, and while this is dubbed a “hunting shirt,” you’re not gonna want to trudge through the forest in this guy. With its high-quality material, structured fit, and nice features like a pleated back (to ensure freedom of movement) and underarm eyelets (to reduce sweating), you’ll be wearing this out to dinner with your girlfriend’s parents, not on a camping trip with your buddies.
Kiel James Patrick Clark Grizwold Shirt
Uber-preppy Kiel James Patrick specializes in creating ropey, nautical accessories popular among the country club set. And while they’re mainly known for their bracelets, they also make a small number of apparel items, like this shirt. Named after Clark Griswold from National Lampoon’s Christmas Vacation, this is a shirt that you can easily wear around your father or grandfather and get their silent approval (which is all you’ve ever wanted, right?).
Topo Designs Mountain Shirt
Colorado-based Topo Designs is mainly known for its indestructible backpacks, but the company’s accessories and apparel are giving the backpacks a run for their money. This Mountain Shirt (available in solid hunter and kelly green, mustard yellow, navy, red, and gray) is made of heavyweight flannel, lined with polyester, and can easily be worn as a shirt on its own, or as a light Fall jacket.
NN. 07 Dexter Checked Shirt
Started in 2007 (hence the 07 in the name), NN. 07 was founded by two friends who wanted to combine the attention to detail from Japanese culture with the minimalist sensibilities of the Scandinavians. This Dexter Checked Shirt uses a classic navy and green tartan that will look good on its own or underneath a sweater when the weather gets extra cold.
Ledbury Blue Peters Flannel
If you weren’t aware that a flannel shirt could qualify as a dress shirt, you’ve never heard of Ledbury. The Virginia-based brand seeks to create shirts that fit so well you feel like they’ve been custom-made just for you. Made from Italian-woven brushed cotton flannel and featuring a shortened body and minimalist collar, the Blue Peters Flannel is the perfect shirt to wear to work every Friday for the rest of your life.
Alex Mill Checked Shirt
NYC-based Alex Mill’s mission is to create essential pieces that every man needs in his wardrobe. The brand succeeds with its Checked Shirt, which uses a combination of red, blue, and yellow to create a classic look that will never go out of style.
Apolis Indigo Flannel
With a name that literally means “global citizen,” Apolis specializes in offering unique, handcrafted goods from across the globe. This solid Indigo Flannel—crafted by a 90-year-old Honduran tailoring operative out of Japanese-milled flannel–is a good way to wrap yourself in the comfort and warmth of flannel without feeling like a lumberjack.
Gitman Brothers Vintage Portuguese Flannel
Similar to Apolis’ Indigo Flannel above, this gray flannel shirt from Gitman Brothers Vintage will look understated and classic while still keeping you warm and cozy.
Outerknown Undercover Shirt
A new brand created by World Surf League Champion Kelly Slater, Outerknown seeks to create quality menswear pieces while using sustainable and environmentally-friendly practices. This means that Outerknown’s offerings aren’t cheap, but they’re high-quality enough to justify the cost. Made from 100% brushed cotton flannel and featuring a slightly asymmetrical plaid pattern, this is one flannel shirt you can easily dress up if the occasion strikes.
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