Plaid shirts have been on our bingo cards all year, but not just any old plaid. We’re talking about the beefy boys of the shirt world: flannels. Thermals and hoodies are the usual layering suspects, but if you want your outerwear to really get in step with the autumnal drumbeat, few things hit quite like a hefty flannel.
Buffalo checks, windowpanes, and those angsty ’90s shadow-plaid brushed button-downs are some of the coziest shirts you can pull from your fall wardrobe, and they look a hell of a lot better than shivering in the name of a fit. The flannel shirts enduring appeal comes from the way it toes the line between bad-boy rebellion and blue-collar grit, and that rough-around-the-edges attitude is what makes them so enduring. Wear one with a denim jacket, workwear pants, beat-to-hell chinos, then finish things off with a pair of derbies if you’re feeling fancy.
From now until the flowers start blooming next year, flannels have the seasonal staying power to carry you through the cold months without making you look like you’ve given up on getting dressed. And remember: The freakier the pattern, the better. For generations Filson has delivered real-deal workwear to countless loggers, foremen, and rangers whose wardrobes demand serious utility.
The Seattle-born brand’s tincloth and heavy wool clothes leap to mind, but its flannels are just as formidable—maybe even criminally underrated. Filson makes a grip of flannel styles, but our favorite is the Rangeland. The brushed cotton is substantial but not suffocating, so you can wear it for at least three seasons (assuming you live somewhere with seasons).
Dual buttoned chest pockets, a blessedly non-dinky collar, and a classic fit come together in a shirt for a shirt that feels like something from the 70s, the flannel’s golden age. It comes in a wide range of colorways and an admirably wide size range, too. A hundred bucks ain’t cheap, but for the quality and attention to details, the value is in your favor.
Fabric 5.5-oz., 100% cotton Fit Classic Colors 10 colorways available Sizes XS-3XL Best Flannel Shirt for Vintage Fiends: Pendleton Board Shirt If you’re looking for a flannel with impeccable vintage credibility and zero thrift store mustiness, there’s only one name to know. Pendleton flannels have been woven in the company’s Washington state mills for more than a century. Thanks to their blend of easy-wearing comfort and rugged western style, Pendleton’s button-downs acquired a loyal following in the ’60s on beaches from Big Sur to Zuma (including The Beach Boys, originally known as the Pendletones).
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