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Before sweater season, before leather weather, fall is the time for flannel shirts. The soft, lightly insulating button-ups are an ideal match for the first crisp days of autumn. If you consider flannel shirts to be the fashion equivalent of pumpkin spice lattes, hear us out. Flannels come in many guises beyond the lumberjack cliché, from refined cashmere dress shirts to versatile overshirts. They’re not just for hipsters anymore—nor were they ever.
Flannel is most often affiliated with its workwear roots, originating in the 17th century as a hardy garment for Welsh farmers. Defined by its soft yet sturdy hand—achieved by carding the yarn, essentially breaking up the fibers for a downier texture—flannel was traditionally woven from wool. In the late 19th century, Hamilton Carhartt brought the textile to America and flannel shirts became the uniform of workmen from coast to coast.
But as any sartorial enthusiast knows, flannel is by no means limited to manual labor. Grey flannel suits became a white-collar uniform during the Mad Men era and remain a smart choice for cold weather. Just google Fox Brothers flannel for a survey of the fabric at its most elegant. We’ll take this opportunity to clear up a common misconception: flannel is a fabric, plaid is a print. The two are frequent bedfellows, particularly when it comes to shirting, but they are not one and the same.
Flannel shirts can be polarizing due to their many associations—Paul Bunyan, ’90s grunge, the Brawny paper towel man—but the style deserves a reappraisal. Any of the following would be a handsome, and decidedly cozy, addition to one’s autumnal wardrobe. Pro tip: avoid pairing them with blue jeans and, whatever you do, don’t accessorize with an ax.
Alex Mill Frontier Shirt
This shirt doesn’t hide its affinity for a weekend in the country. Why fight it? Tartan flannel does look especially at home in pastoral settings. But this option’s shades of cream, ice blue and cherry red make it considerably fresher than the usual country gear. Team it with light-wash jeans and crepe-soled boots for a quietly cool off-duty look.
Portuguese Flannel Lobo Cotton-Flannel Shirt
Portuguese Flannel is a family-run brand that’s specialized in the textile since the 1920s. While it offers numerous variations on traditional plaids, we’re particularly fond of this understated number with a handy pocket in a cool shade of gray.
Todd Snyder Ombre Plaid Flannel Button-Down Shirt
Flannel shirts are often bulky, but in the hands of Todd Snyder, the fall staple gets a streamlined update. This button-down, made of lightweight brushed cotton, in particular, is sharp and tailored, a great companion to a blazer or sleek chore coat. It’s so flattering that it flew off the virtual shelves last year. Which means it’s best to buy it now while it’s still available.
Thom Browne Button-Down Collar Checked Cotton-Flannel Shirt
Slim silhouettes in overcast colors are the hallmarks of Thom Browne—characteristics that don’t often apply to flannel shirts. Indeed, that’s what makes his version of style truly unique. He replaces his signature stripes for checks, but the overall vibe remains quintessential Browne.
Vetements ‘My Name Is’ Check Flannel Shirt
The flannel shirt has surpassed its cabin-in-the-woods origins, finding its way onto the catwalks of Paris. Evidence: This oversized topper from the folks at Vetements, a label that pushes boundaries of design. When it comes to all things cool and edgy, the brand is definitely the name to know and flaunt.
Rag & Bone Pursuit 365 Cotton Flannel Shirt
We’re in the season when the flavor of choice is pumpkin spice. Reflecting this pretty concisely is this rich flannel shirt from Rag & Bone, a slim-fit top made of brushed cotton that’ll definitely heat up any look—and in more ways than one, too.
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Outerknown Blanket Shirt
If you’re a Kelly Slater fan, Outerknown’s Blanket shirt needs no introduction. For the uninitiated, here’s the gist: The topper is one of the warmest and most comfortable styles around, covering the body like a snug hug. It also comes in almost every conceivable color and pattern, which means there’s an option for everyone.
Boglioli Prince of Wales Wool Flannel Safari Shirt
This may just be the perfect layering piece for shoulder seasons. Lighter than a proper jacket but still substantial enough to provide warmth, the four-pocketed design in a natty glen plaid wool works just as well over dress shirts at the office as it does atop tees on the weekend.
John Elliott Hemi Oversized Shirt
John Elliott plays up the flannel shirt’s surfer connotations with this slightly boxy option that has a perfectly worn-in patina and frayed hem. While definitely a piece for off-duty looks, the classic solid olive hue keeps this shirt from looking too grungy.
Officine Générale Judas Judas Virgin Wool-Plaid Overshirt
Camp-collared shirts needn’t fade away with summer, and this shirt makes a strong case for working them into your fall wardrobe. The open neckline has a laidback elegance, particularly when tucked into a well-cut pair of navy trousers. Don’t be fooled by appearances: the pattern has the look of a hefty tweed but is actually woven from fine virgin wool.
Ralph Lauren Purple Label Flannel Shirt
While Ralph Lauren continues to carry the torch for good old-fashioned American workwear, this elevated riff on a CPO is especially handsome. The charcoal and black palette makes it easy to dress up and the almost 50/50 wool-cashmere blend makes it a pleasure to wear.
Aspesi Magra Flannel Shirt
A reverent homage to Ivy style, this is a flannel shirt in the most traditional sense—but the button-down collar and trim cut keep it out of Brawny territory. Lean into the collegiate vibe with a shawl-collared cardigan and chinos, or go full-on with a blue blazer.
Eton Lightweight Flannel Shirt
Yes, this too is a flannel shirt. At first glance, it looks like a textbook blue oxford cloth button-down but closer inspection reveals lightweight flannel with a peachskin brushed texture. Wear it as you would a standard OCBD but with the added benefit of swaddling comfort.
Turnbull & Asser Cashmere Blend Shirt
This is how to do a flannel shirt for the C-suite. The downy cashmere-cotton blend in a pale heather grey will soften formal tailoring and offer a more tactile alternative to standard cotton shirts. Teamed with a classic Prince of Wales checked suit, it’s pure chic.
Anderson & Sheppard Cashmerello Collarless Shirt
As one would expect from a Savile Row stalwart, Anderson & Sheppard’s take on flannel is decidedly refined. The fabric is fortified with 15 percent cashmere and features a small scale houndstooth print, while the band-collared, popover silhouette keeps things laidback. It’s a smart choice for relaxing suits and other tailored fare.