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The Best Flannel Shirts for Men to Layer with This Winter

Ready yourself for the crisp weather around the corner.

taylor stitch the yosemite shirt
Taylor Stitch

You can't spell flannel without fall and now is prime time for the classic shirt to come out of the woodwork and into the crisp air. Like beanies and duck boots, it's a style staple of the season, but it also works well at the end of summer, too, a la Brad Pitt. You'd do well to have a few tasty tartans in your closet. But not all plaid shirts are flannel shirts.

What Is Flannel?

The term has been used interchangeably to refer to plaid at large, though flannel is a specific type of fabric independent of the pattern overlayed on top of it. It's believed that flannel stems from Welsh origins (as far back as 400 years ago) and was originally a type of woven fabric made from carded or worsted wool, which is essentially wool that's been prepped for weaving.

Today, flannel is most familiar as a brushed fabric rendered in cotton, but it can be made with wool as well as man-made materials, like polyester and acrylic. The brushed quality is what gives flannel fabric its softness and warmth, making it a common fabric for chillier months. It's seen in blankets, pajamas and especially shirts, often in some type of plaid, though it can be made in solid colors.

You can learn more about the history of flannel here.

What to Look for


Good flannel shirts are thicker than the usual oxford or broadcloth button-up and get better with age. They're hefty enough to pair with a thermal shirt but soft enough to wear on their own. They're also more versatile than a typical button-up and can do double duty as an overshirt or a shirt-shirt.

Stitch Quality

Cheap flannel is easy to rip. As such, invest in a shirt that's both made from better fabric and put together in a more polished way, meaning the stitches will stay together, not fray or fall apart. $100 or more is a fair price to pay for a shirt that'll last — and you'll want it to.

Why Wear a Flannel Shirt

"Practically speaking, a flannel will bring more warmth and softness than an oxford, but the brushed cotton fabric will also give off a more casual tone," our expert, American Trench founder Jacob Hurwitz, says.

How Should a Flannel Shirt Fit?

"I think a flannel should be a little looser in the body than a dress shirt but also and a little shorter in length," Hurwitz says. "It should drape and not hug every curve and fall below your belt but not below your fly."

How to Pick a Flannel Shirt

While some flannel shirts can feel like costuming, the right one should come naturally, Hurwitz says.

"I don't think flannel always has to feel outdoorsy," he says. "Outdoorsy flannel is usually very heavy (in fabric weight) and rendered in a classic pattern like a check, in a few predictable color combos (like the very trad black/red). But fabric weight is the most defining characteristic and tends to pull everything downstream towards it."

The key to picking the right one, he adds, lies in figuring out your ideal fabric weight. "If the fabric is thick and heavy, the pattern is going to feel heavier and so will the colors. On the other hand, if you take a lighter and finer fabric and brush it (flannel it), you can get a soft and plush fabric that doesn't require a chainsaw or heavy machinery."

His brand's flannel, he argues, is a more modern interpretation, but there are lots out there like it, in newer colors with a proper fit. "It's very sophisticated for being a casual shirt, something you could wear to a modern restaurant with dark denim or trousers and not feel out of place," he says.

The Best Flannel Shirts for Men

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Best Overall Flannel Shirt
Taylor Stitch The Yosemite Shirt
Best Upgrade Flannel Shirt
Filson Alaskan Guide Shirt
Now 66% off
Best Affordable Flannel Shirt
RedHead Ultimate Flannel Long-Sleeve Shirt
Best Overall Flannel Shirt Jacket
Outerknown Blanket Shirt
Best Black Watch Flannel Shirt
Flint and Tinder Everyday Twill Shirt
Best Traditional Flannel Shirt
L.L. Bean Casual Button-Down Flannel Shirt
Now 26% off
Best Modern Flannel Shirt
Wax London Whiting Overshirt
Best Slim-Fit Flannel Shirt
Todd Snyder Flannel Button-Down Shirt
Best Solid Flannel Shirt
Everlane The Brushed Flannel Shirt
Now 38% off
Best Japan-Made Flannel Shirt
Warehouse & Co. Lot.3104 One Wash Flannel Shirt
American Trench Canclini Plaid Flannel Shirt
Woolrich Flannel Check Cruiser Shirt
Pendleton Board Shirt
Ralph Lauren Classic Fit Plaid Flannel Workshirt
Wythe New York Flannel Work Shirt
Portugese Flannel Mill Shirt
Pladra Elli Everyday Flannel Shirt
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