How to Wear a Flannel Shirt This Fall and Winter

Looking for ways to style a flannel shirt this fall and winter? We’ve got you covered! Read on for some top-notch flannel shirt outfit ideas.

The flannel button up shirt is a wardrobe staple that every man should have in his arsenal.

Read on to learn about:

• How a flannel shirt should fit
• What makes a flannel shirt casual
• Flannel shirt outfit ideas

Okay, first we’ll talk about how a flannel button up should fit.

How a Flannel Shirt Should Fit

A flannel button up shirt should fit just like any other casual button up shirt, although it’s okay if it’s a little more relaxed.

Flannel is an inherently casual fabric that’s meant to be functional and comfortable. So your flannel button up shouldn’t be super slim or tight fitting.

Plus, you can use flannel shirts as layering pieces over tees and henleys, so the extra room can be nice.

That said, here’s what to look out for:

First, the shoulder seam should sit where arm meets shoulder (without hanging past that point).

The shoulders shouldn’t be so narrow that crossing your arms across your chest creates tightness or pulling.

Second, the collar should button comfortably without being too tight. You should be able to fit one finger comfortably between your neck and collar.

Since you won’t be wearing a tie with your flannel shirt, you probably won’t be buttoning the top button, so it’s okay if it’s a little bit too tight or loose.

Third, the bottom of your shirt shouldn’t go past bottom of your pants fly when worn untucked. If it hits somewhere around mid-fly, it’s the perfect length.

If your belly is exposed when you raise your arms up over your head, your flannel shirt might be too short.

Fourth, the sleeves should hit your wrist without going past it. They should stop on top of or just past your wrist bone.

A bit too long is usually better than a bit too short, unless you like the cropped look.

Remember: these are just guidelines, so don’t get too hung up the fit 😉

What Makes a Flannel Shirt Casual?

Besides fit, there are some other little details that make a casual button different than a dress shirt.

First, the hem is straight or slightly curved. There are no deep “wings” like you see on dress shirts that are meant to be worn tucked in.

Second, the sleeve cuffs are soft and pliable. There’s no stiff interfacing like you see in dress shirts that are mean to be worn underneath a suit jacket or sport coat.

Third, the collar shape, length and feel is more casual. There’s no stiff interfacing, and point length is often shorter since it’s not meant to compliment a necktie.

Flannel Shirt Outfit Ideas

Now that we understand how a flannel shirt should fit, and the details that make it different from a dress shirt, let’s look at some example outfits.

Just the Shirt

Flannel is a warm fabric, so you might not need any extra layers.

Flannel shirts look great on their own with casual pants like jeans and chinos.

Double Flannel

This only works if it’s really cold outside, but boy does it look good!

This flannel on flannel layering would cause most guys to overheat quickly inside the house or office, but it’s perfect for hiking or working outside during fall and winter.

Flannel Shirt and Fleece

Flannel shirts make perfect base layers because they work well with any casual mid and outer layers.

Try mixing in other textures like a fleece zip up and quilted vest.

Flannel Shirt with a Leather Jacket

Flannel and leather are both tough, thick materials, and they look great together.

This is a textbook example of how good red and black can look together. Bonus points for going with tan boots instead of black (the safer, more obvious choice).

Flannel Mid Layer

I love wearing flannel shirts over long sleeve henleys.

This is a warm, rugged combo that works well on its own or with an outer layer, like a lightweight quilted vest.

Over a T-Shirt

Sometimes your best bet is to keep it simple. A flannel shirt worn open over a crew neck tee? That’s simple.

This outfit would look good with jeans, but I’m loving the casual slim-straight chinos and chunky work boots.

Flannel Shirt and Raincoat

You can also wear light outerwear with flannel shirts. In this case, a tan raincoat looks sharp over a green check flannel and white henley.

This is a functional outfit because the flannel provides warmth, while the raincoat provides water resistance.

Flannel Over a Button Up

Since flannel shirts are heavier and often more relaxed than standard button ups, you can wear them as light jackets over denim or Oxford shirts.

Just make sure your base shirt is somewhat fitted, and your flannel is somewhat relaxed. Otherwise, you’ll sacrifice mobility and comfort.

With a Denim Jacket

Flannel and denim go together like Wes Anderson and Bill Murray: they were simply meant to be.

In this case, the lighter blue jacket and sherpa collar are right at home with the brown flannel shirt.

The dark denim jeans glue everything together while avoiding the wrong Canadian Tuxedo aesthetic.

Flannel Shirt with a Suit

You can wear a flannel shirt with a suit, provided your suit is also made from a heavier fabric (in this case, worsted wool flannel).

Of course, you’re going to want to ditch the tie. Bonus points if your pocket square picks up any accent colors from your shirt.

Over a Turtleneck

Here’s a unique layering combo for those shockingly blustery fall and winter days.

Using a turtleneck sweater as your base layer, wear a flannel shirt unbuttoned, almost like a light jacket or cardigan.

Top this look off with a heavy wool topcoat. On bottom, jeans and boots are perfect, but you could wear wool trousers too.

Flannel Shirt and Chinos

Here’s a simple business casual look for fall and winter:

The green plaid shirt looks great with the acorn colored chinos and dark brown work boots.

With a Field Jacket

Flannel shirts and field jacket have a similar vibe: they’re both products of utility.

Combined, these pieces product a rugged, workwear aesthetic.

Questions About Flannel Shirts

Here are answers to some of the most frequently asked questions about wearing flannel shirts:

Are flannel shirts still in style?

When it comes to men’s fashion, flannel shirts are about as timeless as it gets. No matter what’s trending this year, the flannel button up will always be in style.

What do you wear under a flannel shirt?

Flannel shirts can be base, mid or outer layers. So you can wear an undershirt or t-shirt under your flannel shirt, or you can wear a henley shirt.

You can also wear a lighter button up shirt underneath your flannel shirt (like an Oxford or chambray shirt).

How do you wear an oversized flannel shirt?

Wear your oversized flannel shirts as mid or outer layers. They’ll look good over a henley, t-shirt or fitted button up shirt.

You can wear oversized flannel shirts as mid layers underneath heavier outerwear like field jacket or parkas.

Can you tuck in flannel shirts?

In general, flannel shirts are meant to be worn untucked. This is why they usually have a straight or slightly curved hem.

That said, if they’re long enough to stay tucked, you can definitely wear your flannel shirts tucked in. This looks best with chinos or wool trousers.

Questions? Comments? Leave a comment below!