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8 Great Men’s Flannel Shirts to Wear This Fall

Whatever fall throws your way, these shirts can handle.

The flannel shirt is the Stanley Tucci of your wardrobe: reliable in every single role. Seriously. When the weather dips down, there’s no better shirt to throw on, or over than this classically rugged American essential.

Warm, soft, and available in a wide array of colors and patterns, the best men’s flannel shirts let you stand out or stay traditional. Sure you can go with the classic black and red, but that’s hardly the only option. There’s a flannel shirt that works for pretty much every occasion, from office meetings and apple picking to laid back family days and nights beside a fire.

In any case, the right flannel shirt comfortable and capable of layering in pretty much every scenario. You can wear it over a long sleeved shirt or a graphic T-shirt. A more subtly patterned flannel works under a blazer for business casual. And, of course, a flannel works all on its own, sleeves rolled up. From rugged to office ready, here are some of our favorite men’s flannel shirts to wear.

The Jackson Flannel takes the traditional fall plaid pattern and shakes it up with rich tones of Walnut and Rust. That stand out color scheme makes it all the better to style with a trusty pair of blue jeans. Color aside, this is a shirt you’ll want to wear all season: The double-brushed fabric is incredibly soft, while the diagonal-weave cotton twill is quite durable.

There’s a good chance you remember the trusty flannel worn by your dad or grandpa on cold fall weekends, right? Howler Brothers manages to translate those memories into a modern interpretation of a vintage-style flannel, complete with a retro color scheme that calls to mind the 1970s (in a very cool way). It’s the ideal shirt to wear around a bonfire, given that it’s cut from a heavyweight blanket flannel fabric. Don’t leave home for that camping trip without it.

While you certainly can’t go wrong wearing a plaid flannel shirt, it’s nice to consider other options for your rotation. In this case, Lands’ End offers up a surprisingly refined take on the flannel shirt, pairing brushed flannel fabric with a handsome, solid color. Think of this as a “dressy” flannel shirt, best worn with wool trousers and sharp leather Chelsea boots for a fall dinner party.

How to Roll a Shirt Sleeve The Right Way

There are multiple schools of thought and plenty of tutorials on how to fold a shirt sleeve. You don’t want sloppily rolled sleeves that hang off your elbows, nor do you want shirt sleeves rolled too high and tight. Our advice: Go for a happy medium, especially as flannel is a heavier fabric than, say, a more traditional Oxford cloth shirt. 

Here’s how to do it: Unbutton the shirt cuff button and the “gauntlet” button (the button or buttons slightly further up the sleeve on your forearm). Flip the shirt back one cuff length, and then roll the fabric over once (or twice, your call!), before tucking the corners in, for a cuff that hits mid-forearm and stays in place. 

A casual, cool flannel shirt best worn with dark blue jeans and paired with an Oktoberfest beer any night of the week. The grey and red plaid pattern is a nice change of pace from the more common red-and-black plaids, too.

The flannel shirt takes on a decidedly moody, Western-inspired look here. Dusty blue pops nicely against the multi-stripe black plaid pattern, the kind that in turn wears especially well with tan chinos or faded black jeans. As if that wasn’t enough, this Japanese cotton flannel shirt fits trim, but not too tight, making it the perfect flannel to wear with sleeves rolled up.

There are times when nothing less than a rugged flannel shirt will do, especially when your to-do list keeps piling up on chilly fall days. This aptly named — and very affordable — flannel features UPF30 sun protection as well as handy add-ons like a hidden side zip pocket, button chest pockets, and the ability to be layered over a warm thermal base layer.

The Yosemite Shirt from Taylor Stitch has been a fan favorite for years, likely because of the fact that it’s built with flannel chamois (Flannel, but even softer). It’s a versatile piece that’s ready ready to layer over a henley or a T-shirt and this fall, they’ve even introduced a range of rich seasonal colors. Our favorite is this flecked Nutmeg variation.

For more than 200 years, Scottish soldiers have worn some form of the deep blue and green black watch tartan pattern. This tailored, soft flannel shirt brings a bit of that history. It’s warm, able to be layered over just about anything and is best worn untucked.