Best 15 Tips On How To Style A Flannel Shirt From Casual to Smart in 2023

You now possess the best flannel shirt, having searched across the kingdom far and wide for it. But the real question is, how to style a flannel shirt? “It’s a shirt… c’mon guys,” I hear the fashionistas saying. And yet think of the endless nebulae of connections and combinations. It can quickly become a galaxy of confusion. The question of how to style a flannel is similar to philosophical inquiry (and at least equal in gravitas too). So, let us explore the most viable possibilities. But first, your history lesson.

The flannel shirt is an affordable, breathable, water-resistant, and highly insulating garment. Hence why it has enduring appeal. The origins can be traced back to Wales in the late 1600s when farmers made garments from leftover wool, which explains the tartan/plaid use today. “Gwlanen,” meaning woolen cloth in Welsh, is reportedly the origin of the word. Although “flaine,” meaning a kind of coarse wool in Old French, might have a reasonable claim too. The flannel fabric is combed to raise the surface via a process called “napping,” giving the flannel its fuzzy and warm texture.

The garment eventually landed on US soil, where the US Army used it as an undergarment in WWI. Throughout the 20th century in the USA, it was adopted as the outdoor working man’s shirt, thanks to workwear specialist Hamilton “Ham” Carhartt. It was solidified in the American frontier mythology by Paul Bunyon, a folklore character who stood for American self-sufficiency and would often wear flannel shirt outfits hence its association with lumberjacks.

Then a lad called Kurt Kobain came along, and so began the crossover from the rural to the urban. Then, it became the uniform of the early noughties hipster. And now? With all those piled-up historical allusions? What to do with the semantics of your flannel shirt? How to style a flannel shirt with all that reference? My only consolation to this confusion is that FashionBeans is here to show you how.

If you want to save from looking like a discarded towel and look more like a modern-day, swaggering Flañeur learn how to style a flannel shirt by continuing on this journey.

1. Flannel shirt with jeans

It’s the classic flannel shirt look because it’s extremely hard to mess up. Wake up in the morning, throw on a flannel shirt, some high-quality jeans, pair with any number of shoes and sneakers, and be bloody done with it.

And now for the how to style a flannel shirt outfit guidance:

All jeans are welcome (except skinny ripped jeans, but that goes without saying). When wearing plaid (check), think about matching the minor color in the check closely with your jeans—if black and red check, the black check. Hence a white and blue check would go well with white, ecru, or off-white jeans. Or a green and blue check with indigo jeans.

2. Casual flannel outfit

The flannel shirt is generally considered a casual item. But, how to style a flannel for men in a casual way that isn’t mundane or lacking in inspiration? Consider pairing your shirt with a gilet. This will lend the outfit a more athletic slant, plus, with bonus warmth, ideal for the transitional seasons. Or try pairing it with a sweater vest, in line with current trends.

On your bottom half: jeans, cargo pants, chinos, and for a very casual feel, you could pair it with some joggers. Wearing a casual flannel outfit would generally point to wearing comfortable sneakers too. Can’t go wrong with a pair of Newbies.

Plaid flannel shirts particularly work well as a casual choice. So if you’re struggling with which is the best plaid flannel shirt to choose, FashionBeans has you covered.

3. Smart casual flannel outfit

There is but one unbreakable rule when getting down to how to style a flannel shirt in the smart-casual genre: DO NOT WEAR PLAID. And then, I’m going to immediately break that by saying there’s a caveat if it’s a high-quality micro-check. Then it’s acceptable. Welcomed, even.

The joy of flannel shirt outfits is that you can generally bring more texture because of the material’s fuzzy outer. Try wearing a chunky knit or sweater over the top of your tucked-in flannel with some chinos and smart-casual chukka boots or moccasins. You can even add in a long textured overcoat and step up to some brogues or Chelsea boots if you want refinement.

4. Flannel shirt with a leather jacket

I write this whole paragraph *gulp* particularly despising the biker jacket-plaid shirt combination. So, I thought I’d challenge myself and find ways on how to style a flannel shirt with a leather jacket and actually look good doing so.

First, it doesn’t have to be a plaid shirt. A plain-colored flannel shirt will mesh better with a wide range of leather jackets. Second, try keeping everything dark and in synchronicity. Third, try a baggier fit both for the shirt and the jacket, and let the creases and spaces do some of their own aesthetic work. Fourth, it doesn’t have to be a biker jacket. Other jackets, such as a simple straight zip and collar in a dark brown, can sometimes go well with a flannel shirt and jeans. Lastly, try suede. The texture of flannel and the texture of suede will make a nice contoured topological map of fashion up top.

5. Flannel shirt with a hoodie

How to style a flannel for men… with the laidback yet chic introduction of a hoodie? Simple. The hoodie-flannel shirt outfit is easy to master and brilliant for when you have to do menial chores but still want to look swag. The hood hangs over the shoulder a little, giving a little more nonchalance than just a t-shirt. It’s comforting and looks decent—win-win.

We recommend going with a baggy flannel shirt since hoodies tend to be capacious. Remember, the plaid pattern works well against a single-color hoodie. It might also be worth investing in a flannel coat or a lined flannel shirt to construct one of the coziest casual looks for the winter.

6. Oversized flannel

How to style a flannel for men in the super en vogue style of oversize?

When going oversized it’s worth noting that other layers (except for a t-shirt underneath the flannel shirt) will have to be baggy too. So, avoid skinny-leg chinos or jeans. Otherwise, it will all look at odds with itself. With a baggier shirt and baggier trousers, this means you can indulge in some chunky-soled sneakers (or Vans for a nice grunge look). Don’t be afraid to try chunky derbies or brogues, which are in fashion at the minute. You also have permission to wear a cap. Go wild, you crazy thing, you.

7. Flannel with shorts

Ah, the old cabriolet version of flannel shirt outfits. Getcha knees out because we’re getting you BBQ-ready. But… which shorts, exactly? I’m just looking now, and there appear to be whole articles written on this topic. Oh, thankfully, FashionBeans has written one of them.

Now, how to style a flannel shirt with shorts. The classic go-to is a black/white baggy flannel shirt with a pair of cream baggy shorts, athletic ankle socks, and white sneakers. This is a nice summer flannel look. Don’t be afraid to add a little jewelry to this whole shebang too. And, if you’ve been dabbling with the idea, now’s your chance to get that tattoo while you’re at it. Summer’s the time to flaunt it. Unless of course, you go for the pan-seasonal face tattoo…

8. Styling a red flannel shirt

Let’s get grungy, baby. Before we get into particular looks, some tips. I suggest a slightly dusty red or burgundy to avoid the brightness that comes with a vibrant red plaid check. It can also be harder to style. Also, avoid a plain red flannel shirt again since it can be difficult to pair up.

Downstairs, black jeans and black boots can be nice, but it’s quite Middle-America-generic. Perhaps opt for a cut-off light wash jeans, a pair of Converse, and a white t-shirt underneath for a “nu-skater” look.

9. Styling a black flannel shirt

Forget steam-punk, pop-punk (go drink a vial, Machine Gun Kelly), or actual punk, there’s been a new punk in town for a while: Insta-punk. The black and white plaid shirt, with ripped black jeans and a leather jacket, has been the Insta pin-up in certain quarters for a while now. So, that’s one route. But, as social media critic Robert Frost once said, “Insta-punk has become a bit too traveled now.”

Our advice on how to style a flannel shirt in black? Try slipping in some gray or off-white loose-fitting jeans with the plaid black shirt. Or, a plain black flannel shirt, with all of its wintery texture, can make for an extremely versatile item of clothing. Pair with chinos, and derbies and you’ll be waltzing into the office with renewed vigor.  

10. Styling a gray flannel shirt

Flannel is not just for Christmas. Nor is it just for shirts. Since the mid to late 20th century, it’s been used as a tailoring fabric to great effect, thanks to its excellent insulating qualities. The gray flannel suit became such a phenomenon that in 1975, scent maker Geoffrey Beene made it the name of one of the first designer scents ever. So, just know when you’re working out how to style a flannel shirt in gray, a bit of history is very vaguely attached to it. (See our best flannel-lined jeans article for other loosely flannel-adjacent content.)

We recommend leaning into a lighter space with the gray flannel. Whether you go with the “n” or the “d” version (plain or plaid), we suggest beige trousers, white sneakers, and a white t-shirt for a classic look. A darker option is with navy chinos, a navy parka jacket, and some oozingly comfortable New Balance sneakers.

11. Styling a green flannel shirt

Light or dark? This is not a choice between good and evil. It’s the question that helps answer the question of how to style a flannel shirt in this beautiful tonal green I just bought? The question is still the same for plaid or plain.

Light is the summer version. We suggest wearing white jeans with white or ecru sneakers (preferably with a light brown gum sole visible, but we’re not being too precise here). A tote bag wouldn’t hurt either. Dark is the autumn version. Try a navy or gray t-shirt underneath, rolled-up unwashed indigo Japanese denim jeans, brown boots, a beanie (for the chill), and cool shades (for those daggering horizontal rays).

12. Styling a brown flannel shirt

There are many a-shade of brown: Camel, chocolate, sandy, beige, and dusty. They have a wonderful range of expressions, from bright summer to deep winter. For a wintery inflection, try a chocolate brown flannel; we suggest giving texture to the outfit. Try it with thick wale cords, brown moccasins, and an oversized coach jacket.

But if it’s the check style you’re after, then firstly, read this piece on the best check shirts. Whatever your brown checked weapon of choice may be, it’s bound to suit an all-year casual look of mid-wash jeans, an off-white t-shirt, and some ecru sneakers.

13. Shirt under flannel 

This is ground-breaking stuff, guys. If you wear a t-shirt under a shirt, it looks good. There are mistakes to watch out for when considering how to style a flannel shirt with a t-shirt under, though. We recommend not really doing up your shirt or only doing up a few buttons to keep the flow and intentionality of the background t-shirt color.

If you’re cold, layer up with a puffer jacket in a similar tonal range. Alternatively, you can button it all the way up to the top, just showing the smallest bit of the t-shirt, or completely up to the top, covering the t-shirt. In the UK, the full button-up has a very 2008-blown-out-photos-of-eighteen-year-olds-doing-jaeger bombs-at-uni vibe, but you never know, it could come back around. At the rate fashion is eating up historical aesthetics, it might well be.

14. Flannel under flannel

Woahhh, Jonny Two Shirts, steady on pal. Why, why don’t you just put down the vape there son, and take off one of your shirts? You’re causing a ruckus. 

Wearing two shirts is a totally normal, cool thing to do. When it’s done right it can be a searing indictment of how we should loosen up our dress codes and embrace novelty. And when done badly… no, it’s always a searing indictment, actually.

One rule on how to style a flannel shirt under flannel: wear a plain shirt underneath and a plaid over the top. If you want to truly let your head spin off its axis, wear a roll neck underneath the plain shirt and a coat over all three. That son is textured layering. And you can pick the vape back up now.

15. Hiking in flannel

The flannel shirt makes an excellent hiking accouterment. Not only is it more stylish than regular thermals or GORETEX, but it also has adequate hiking capabilities. (Please don’t take only your flannel shirt to K2). The natural insulation, breathability, and soft water repellent nature make it a hikers’ friend.

As for styling, some sturdy cargo pants (in fashion), some trail running or hiking shoes (in fashion) can be found by almost every brand these days. The advantage is you’ll look, you guessed it, in fashion even off the trails.

Final Verdict 

There are numerous ways to approach the question of how to style a flannel. Here are our top tips to remember:

• Remember, it’s casual. So the flannel shirt works best with jeans, chinos, and cargo pants.
• Color match. When styling plaid match, one of the colors is close-ish to the color of your pants.
• Be brave with layering: try gilets, sweater vests, double-shirts, overcoats, coach jackets, roll necks, etc., etc.
• Never wear ripped skinny jeans. Period.’