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How to Style a Flannel Model Wearing Flag Anthem Flannel Sitting on Staircase Outside
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How to Style a Flannel: The Essential Guide for Men

Savarone Ammann

Fitness, Personal Growth, Style, Grooming, Lifestyle

Sav works as a senior copywriter at Codeword Agency and has written for brands ranging from Google, Android, and Salesforce to TRX, Onnit, Soludos, and Ben Sherman. He describes himself as an overly active inkslinger with a touch of self-proclaimed style and an affinity for the perfect glass of red wine. He believes, like the color black, being a gentleman never goes out of fashion. Read full bio.

Last Updated: Feb 23, 2024
10 min read
Key Takeaways

Flannels are tricky. Why? There are tons of right and wrong ways to style them. I like wearing a flannel buttoned up with jeans or chinos, or unbuttoned with a henley or solid-colored t-shirt underneath. However you choose to wear a flannel, just be sure you aren’t wearing other patterns or bright colors that will clash and look off-putting.

Flannels are softer than your other button downs, warmer than your other button downs, and easier to screw up wearing than your other button downs. 

Hey, it’s a trade off, I guess.

Here’s my guide on all the ways to properly style a flannel without creating a trainwreck of clashing patterns.

What Is a Flannel?

Model in woods in Flag Anthem flannel
Trekkin’ in the Flag & Anthem Linden Herringbone Flannel

Flannels are a garment that will seemingly forever hold down a place in the working man’s wardrobe—both while on and off duty.

Flannels are button-down shirts made from soft-woven fabric, typically either cotton or wool. Flannel material is milled or raised, creating a thicker, sturdier texture than what you’d find in other button-downs or casual linen shirts.

These shirts are often worn in cold-weather areas and seen as a vintage-inspired garment with roots in western style. 

Plain vs Check Flannel Differences

Rolled sleeve of Flag Anthem shirt

Checkered flannels stole the limelight in mainstream fashion, but you can find excellent plain, solid-colored flannels, too.  

The material in these two styles is the same, only the appearance is different. But people commonly associate flannel shirts with having a checkered pattern.

I like to go with plain, solid-colored flannels for a more urban, subdued vibe. And since colors like charcoal, gray, black, and tan tend to look good on me, I lean into those when I’m in the market for a new flannel. Think about what color shirts you already wear to pick your flannels accordingly.

Checkered and patterned flannels come in endless variations of lines, squares, and intricate designs. It’s up to you to decide which patterns will best suit your style and personality. To start, go with simple checkered patterns that match most of the pants in your wardrobe, then slowly dabble further into wilder, louder patterns as you see fit.

When Should You Wear a Flannel Shirt?

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Flannels are inherently a casual working man’s shirt, which means they’re suitable for most everyday occasions. But keep in mind, flannels are a bit too casual for formal gatherings and business offices.

If you’re working outside in cold weather, heck yeah you should throw on a flannel. But even if you just want a nice-looking warmer shirt to wear with jeans and a t-shirt, a flannel is a tremendous option.

I prefer wearing a flannel by itself with dark jeans, but plenty of dudes stylishly layer flannels with a t-shirt underneath or a light jacket or vest on top.

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Like I said, formal occasions are off limits, so if you’re wondering if you can wear a flannel with a blazer, I’ll squash that notion right now and say nope. 

Flag & Anthem has one of the best collections of men’s flannels I’ve ever found in a variety of stylish patterns and colors, as I noted in my recent review of the brand. The biggest and best difference I found is that these guys cut their flannels into a tailored, athletic fit. This looks much better than the baggier alternatives you’ll find elsewhere.

I have a couple of their 100% cotton flannels, including the Linden Herringbone Flannel below, and they’re about as thick, soft, durable, and fitted as they come. 

Flag & Anthem Linden Herringbone Flannel

I prefer flannels made of 100% soft cotton and the Linden Herringbone is exactly that. This flannel shirt was my favorite of my latest haul from Flag & Anthem; a versatile grey pattern that pairs with almost every color of pants and gives you a cozy, subdued look.

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Ways to Wear a Flannel Shirt

Model walking in Flag Anthem apparel

Because they’re versatile, casual shirts, flannels can be worn in a couple of different ways. 

Like I mentioned, I prefer to wear flannels untucked and buttoned up with jeans or chinos on their own. Leaving out the undershirt allows you to feel the cozy material directly on your skin and show off a bit of chest while you’re at it.

If you want to wear a flannel unbuttoned for an even more casual look, just be sure you pick a clean, solid-colored t-shirt to wear under it.

Sleeves are always fair game. Leave them unrolled or roll them up a couple times depending on your preference. If you’ve got your favorite watch on, I say roll ‘em up and let your timepiece catch a few glances.

Lastly, a good flannel should fall right below your waist, meaning you can and should wear it untucked. Unless you work a physical job and find yourself around hazardous equipment. In that case, keep it tucked in or risk getting it caught in the metal teeth of an excavator. Don’t want to think about that. 

12 Stylish Flannel Shirt Outfits for Men

Casual Flannel Outfits

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A simple gray-patterned flannel with jeans is a timeless outfit that doesn’t miss. Rolled up sleeves add to the laid-back vibe here and work quite well with this combination. The flannel above is called the Dyer Vintage Washed from Flag & Anthem’s collection.

Flag & Anthem Dyer Vintage Washed Flannel Shirt

Beyond its soft feel and stylish untucked fit, the Dyer Vintage Washed boasts a sharp, but simple pattern that'll bring plenty of flannel-value to any guy's wardrobe.

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It’s a sharp, but simple pattern that looks good on tons of different guys.

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A brightly-colored, patterned flannel takes center stage in a casual fit. Just pair it with neutral pants and shoes so you don’t run into clashing patterns. Casual doesn’t have to mean boring, gents.

Smart Casual Flannel Outfits

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Maybe you don’t look like (or hit like) pro running back Christain McCaffrey, but you can easily dress like him. Find a jacket that accents your favorite flannel and wear them together. Now you’ve got a thoughtful pairing that shows you dress with intention. McCaffrey is rocking the Peters Flannel in the picture above.

Flag & Anthem Peters Flannel Shirt

Crafted from 40% cotton and 60% poly for all day soft comfort, the Peters looks equally as good tucked as it does untucked thanks to its well-thought-out 29.5" length. We like.

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A soft, light-weight flannel with a bold navy, brown, and rust pattern.

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Achieving a smart, but casual look is easy if your clothes fit well and complement one another. Tapered jeans, a crisp neutral-toned t-shirt, and a small checkered flannel worn unbuttoned? Yep, that’ll do it. 

Red Flannel Outfits

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Red flannels may remind you of lumberjacks and they don’t look good on every guy, but if they suit your style, let it be the standout piece of your outfit. I’d recommend pairing it with jeans or chinos and a black or white t-shirt underneath. 

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Aside from contrasting the rest of your outfit, red flannels also deliver more visibility than other colors. If you’re hiking, and especially if you’re hunting, they’re a great choice to help keep you warm and keep you seen by, you know, other guys trotting around with powerful rifles. 

Green Flannel Outfits

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Unlike bright-colored flannels, gray flannels won’t steal the show, but can instead give you a slightly more elegant look while still falling into the category of “casual shirts”. Worn buttoned-up with fitted khakis like we see here is stylish but versatile. It’s a fit that would hold up for dinner, a date, any all types of casual gatherings.

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On the contrary, you could roll the sleeves up and wear a gray flannel open for a fully casual streetwear fit. It’s all about how you wear a flannel and what you style it with.

White Flannel Outfits

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White-patterned flannels will pop when paired with solid dark colors like black or gray. This outfit works because the flannel snags all the attention while the black pants and undershirt blend together in the background.

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“The Boss” can wear a flannel. Bruce Springsteen rocking a white-checkered flannel with an undershirt is a classic country look a lot of guys can pull off. Snap open the buttons, roll your sleeves up, and toss on your best pair of denim. Good to go.

Brown Flannel Outfits

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Flannels are one of the best types of button-downs for outdoor adventures. A good flannel will offer warmth and durability against the elements while providing a modern cowboy look you just can’t achieve with much else. Grab your best brown flannel, boots, and a beat up pair of jeans to meet Mother Nature head on. 

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A brown flannel can be as stylish as it can be rugged and outdoorsy. This two-toned brown flannel looks great by itself—no undershirt needed. Paired with a fresh haircut and slim jeans, it creates a stylish ensemble you could wear out for a date or at the holiday dinner table with family.

How to Style an Oversized Flannel

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Deciding how to style an oversized flannel depends on why you’re wearing an oversized shirt in the first place.

If you enjoy wearing loose-fitting shirts for comfort, that’s fine. Just be sure your flannel is the only oversized garment you’re wearing. If your pants and undershirt fit baggy too, you’ll look careless and disheveled. The loose-fitting shirt jacket above from Flag & Anthem is called the Summit Hooded Shirt Jacket.

Flag & Anthem Summit Hooded Shirt Jacket

We love this rustic shirt jacket as a layer and if you're into soft plaid hooded jackets that are built really well, we think you will too.

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This casual outfit works because while the shirt jacket is oversized, the jeans and henley fit just right.  

If you’re wearing an oversized flannel to make your frame appear bigger and bulkier, you might need a thick shirt underneath to help fill it out. I’d recommend a long-sleeve thermal henley with some weight to it. Flag & Anthem makes a killer brushed thermal henley that has the perfect thickness.

If you’re just wearing an oversized flannel for extra warmth and trying to cram as many layers as possible beneath it, then do what you go to do man. 

How to Wear a Flannel Shirt: The Rundown

Model sitting in Flag Anthem flannel

Flannels are soft, durable shirts that can be styled in a ton of different ways. Because they exude a classic western vibe, they look great when paired with jeans and boots.

But quality flannels extend far beyond western wear. They’re timeless shirts that add a little flair to any casual outfit.

If you gravitate toward brightly-colored or patterned flannels like the one above, make sure everything else you’re wearing is monotone to avoid clashing colors and patterns.

While they’re a newer brand on the market, Flag & Anthem is making some of the best flannels I’ve ever buttoned up in a range of colors and patterns. And unlike other brands, theis have a tailored athletic fit which makes a huge difference. 

Flag & Anthem Madeflex Plaid Hero Knit Flannel Shirt

The added stretch of the Madeflex Plaid Hero Knit Flannel delivered by a blend of polyester, viscose, and spandex makes this shirt easy to move in. While I’m usually reaching for a flannel because it’s soft, thick, warm, and durable (not stretchy or performance-oriented) I still think this flannel is a winner due to just that.

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Remember, you can wear a flannel buttoned up by itself, or unbuttoned with a single-colored t-shirt underneath. You can wear a henley beneath a flannel or a vest or light jacket over it. You can roll up the sleeves to show off your favorite watch or leave them down. Have a bit of fun with it and do what feels the most stylish for you.

Flannels will forever hold down a firm place in men’s fashion, so pick up a couple of good ones, you won’t regret it. 


What kind of shoes should you pair with a flannel?

Flannels inherently give off a western, vintage-inspired look. This means boots typically pair well with them. However, you can wear chelsea boots, sneakers, or oxfords with the right style of flannel and pants.

Should a flannel be buttoned or unbuttoned?

You can wear a flannel either buttoned or unbuttoned depending on which style you prefer. If you opt to wear it unbuttoned, be sure you have a clean fitted t-shirt or henley on underneath.

Can you pair a flannel with a blazer?

Nope. Flannels are one of the most casual-style of button downs you’ll find in men’s fashion, which means they shouldn’t be paired with something as dressy and formal as a blazer.