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How To Wear a Flannel Shirt on More Than Just Cold Days

Updated on September 29, 2024 by Karlton Miko Tyack · Clothing and Style

When it comes to how to wear flannel shirts, there are a world of ways to do it. Here are some tips to help you incorporate this fall and winter piece into your personal style.

Photo by vectorfirst / Depositphotos.com

Autumn is my favorite season. I love fall style and getting cozy with layers and outerwear. I also firmly believe it’s the best season for menswear. Neutrals like tan and olive always look good. And even if all you have on is a tattered white T-shirt and blue jeans, a nice peacoat will spruce that combo right up.

So today, I’m going to go over how to wear a flannel shirt — a true fall and winter staple. Of course, flannels are most natural during cold seasons. However, you can wear an unlined flannel on any day that isn’t steaming hot. It’s just a matter of how you style and rock it. That’s what we’ll learn here.

Table of Contents

Toggle
  • What Is Flannel? Plaid vs Flannel
  • How To Wear a Flannel Shirt: Fit First
  • Good Flannel Shirts: What Makes One “Good”?
  • How to Style a Flannel Shirt Year-Round
  • For Winter: Men’s Lined Flannel Shirt
  • FAQs
  • Conclusion: A Versatile Garment

What Is Flannel? Plaid vs Flannel

Photo by Dayvison Tadeu / Pexels.com

Often, people think of flannel and plaid interchangeably. Or, they believe all flannels have plaid. That’s not the case at all. 

A flannel is a medium-weight, soft fabric commonly made with cotton or wool. It often has a napped finish, though how napped it is depends on the weave. Manufacturers use flannel for many things, including blankets and, of course, shirts. The flannel shirt is a casual button-up that usually has pockets. 

Though we call these shirts “flannels,” that word technically refers to the fabric itself. From here on out, though, when I use the word “flannel,” I’ll refer to the flannel shirt, not the flannel fabric. So, a flannel can come in many colors and patterns, most commonly plaid. This is why people mix the two words up. It can also be lined or unlined.

Plaid is a pattern made up of intersecting vertical and horizontal stripes. The intersecting lines vary in thickness and color. Plaid has an interesting history; Scottish tartans inspired the print, which they used to differentiate the different tribes in the country.

How To Wear a Flannel Shirt: Fit First

How a flannel shirt should fit

Before we go into styling flannels, let’s talk about fit. A flannel button-up shirt fits like any other casual button-up. This means clean lines that follow the actual shape of your body. However, since many people wear flannels as outerwear, they can be more relaxed than a button-down.

Since flannel shirts are meant to be comfortable, functional, and practical, you don’t want them to be too slim. In fact, a slightly looser size is better than a tight-fitting one. 

The shoulder seam should sit where the arms meet the shoulder and not go beyond that. I’ve said this often, but shoulder fit should always be secure yet mobile. Regardless of whether you’re wearing oversized fits or regular ones, the shoulders will create the drape. And you always want it to be clean. You’ll notice that even as fits and cuts considered “classic” change throughout time, the shoulders remain the same.

You must be able to fit one finger comfortably in between your collar and neck. This means that the collar button sits comfortably, not tightly.

The body of your shirt shouldn’t go beyond your pant zipper if it’s untucked. The perfect length? It should hit somewhere in the mid-pant zipper. A little past or above that is okay. But you don’t want it to be more than half an inch from the middle. Basically, you don’t want your belt to show when you raise your arms.

Finally, the sleeves should stop at your wrist, not past it. The hem must sit on top of the wrist bone. Again, just a touch under or beyond it is okay. These are simple guidelines, as I know some of you prefer a slimmer or looser fit.

Good Flannel Shirts: What Makes One “Good”?

Good flannel shirts are made from high-quality fabric, meaning they’re thick and durable but also soft and cozy. If the fabric is itchy, uncomfortable, or flimsy, that’s not a good sign. A good shirt isn’t as heavy as a wool sweater and certainly won’t be as heavy as a jacket. However, it should have heft, not bulk, so you can wear it as outerwear if you want to or need to. 

Most premium flannel shirts are brushed on both sides, making them even softer and showcasing some loft. 

As with any garment, you want to look for tight stitching and reinforced seams. This is especially important on the collar and cuffs. Make sure the buttons are double-stitched. Flat-felled seams are particularly sturdy. The fabric’s raw edges are encased within the seam and then stitched down to ensure they’re perfectly flat. 

How to Style a Flannel Shirt Year-Round

Most people associate flannel shirts with the fall and winter. Yes, this is because most wear flannels in the colder weather. But don’t let that stop you from cozying up to a soft flannel in the warmer months as well. Depending on where you reside, spring climates are unpredictable. Additionally, summer may bring cool evenings, especially on the coast. 

Color and fabric are the tricks to transitioning your flannel from fall and winter to spring and summer. Opt for a lightweight flannel in the warmer months and choose a color appropriate for the season. Instead of navy or olive, opt for lighter and brighter blues and grassy greens. 

Can’t picture it? Check out the pairings below to spark inspiration. 

Warm Season Flannel Looks

 

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A post shared by SAWAKO @Kyoto Japan👘🌸🇯🇵 (@waru1322)

Finally, you can indeed incorporate flannel into warm-season casual outfits. Sometimes, there are cool summer evenings or breezy spring days. Some brands do, in fact, make flannels in summer and spring colors like yellow, light pink, and sky blue.

Just remember to stick to unlined models. They’ll end up just feeling like soft, slightly heavier button-down shirts but with a looser, more workwear-adjacent fit.

Fall Flannel Shirts: Style Inspiration

Photo by nejron / Depositphotos.com

Here are some looks that incorporate fall flannel shirts! As mentioned, you can wear this timeless garment in other seasons, too. However, it’s definitely made for a fall wardrobe, which is why we’re starting here.

In the fall, you can wear neutral shades like olive, tan, and gray. You can also go for brighter autumn colors like burnt orange, rust, and mustard. As you’ll see in these examples, you can even wear your flannel as a shirt or as a piece of outerwear.

Winter Looks: A Fleece Flannel Shirt and Layers

Turtleneck Layers

Now, here are some winter outfits!

You can continue to wear your fall flannels in the winter. However, a fleece flannel shirt, or any shirt with a lining, is most practical. It also provides a weather-appropriate aesthetic and texture. While layers are essential on the coldest days of autumn, they’re mandatory in winter. If it’s extra cold, there’s nothing wrong with wearing an open flannel over a closed one.

You can even start incorporating darker colors, like charcoal and true black. Go for black jeans and a dark Sherpa-lined flannel. As we approach the holidays, winter whites, creams, and more celebratory green, red, and blue hues are also appropriate.

For Winter: Men’s Lined Flannel Shirt

Photo by Bannon Morrissy / Unsplash.com

When it comes to looking for a good winter flannel, men’s lined flannel shirts are your best bet. Fleece lining adds comfort and warmth. The synthetic fabric is made from polyester fibers, which help with insulation as well as protection from cold air.

Sherpa is a soft, fuzzy fabric that’s heavier and thicker than fleece. This is because it’s a mix of polyester and acrylic. This often means it’s warmer but also bulkier. Alternatively, a quilted lining keeps warmth while giving the shirt a classy, sportier look. Quilted linings allow your shirts to maintain their shapes, even after repeatedly washing them.

FAQs

Here are some common questions, as well as their concise answers, regarding wearing a flannel shirt!

Should Flannel Shirts Be Tucked or Untucked?

You can wear a flannel shirt tucked or untucked. It’s a casual piece of clothing, which is why you don’t need to tuck it in. However, it’s also structured, like a button-down, so it won’t look unnatural if you did tuck it in.

Do You Wear Something Under a Flannel Shirt?

Typically, you’d wear an undershirt beneath your flannel. It can be a tank top, a light T-shirt, or even a thermal top. If you wear your flannel open, you can wear a regular top underneath.

What Shoes To Wear With a Flannel Shirt?

Flannels are a cold-weather and outdoorsy staple, so they pair well with boots. However, you can wear any casual shoe with them, including sneakers, moccasins, and even loafers.

Conclusion: A Versatile Garment

Now you know how to wear a flannel shirt. The key here is to get a flattering but comfortable fit. From there, it’s pretty easy. Jeans and sneakers? Go for it. Work pants and service boots? You can’t go wrong.

Even more, you can wear this winter and fall staple on warmer days if you choose the right construction. Of course, in my opinion, the best time to wear a flannel is definitely autumn.

What do you think? Questions? Comments?

Clothing and Style button down shirts, button up shirt, flannel

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About Karlton Miko Tyack

Karlton Miko Tyack is a freelance writer covering watches, gear, and style. He was born in LA, studied art history in Boston, and is a lover of rugby, football, and optimism.

Background: Karlton studied art in Boston while working in local galleries. This led to a career in corporate art consulting, hunting down the perfect pieces for specific brand or business.

Transitioning into freelance writing, he moved back to his hometown of Los Angeles, where he managed top accounts with art publisher TASCHEN. His clientele included prominent names in fashion, luxury, and sports.

He then moved to NYC to work as a client liaison at Sotheby’s auction house in New York, where he worked with collectors of fine art, as well as watches, wine, and whiskey.

A lifelong watch enthusiast, Karlton has worked with quality timepieces of all price points and calibers, vintage and contemporary. Tyack’s watch obsession began when he received an Omega Seamaster for his 15th birthday.

Expertise: Through his work in fine art and with Sotheby's auction house, Karlton has developed a deep knowledge of timepieces, whiskey and menswear. He's written for publishers like LA Weekly and Harvard. Here at TMM, Karlton covers watches and men's fashion.

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  1. John says

    January 2, 2024 at 4:46 pm

    What brand is the blue plaid flannel that you’re wearing in the first photo? Being 5’6″ it’s hard to find shirts that fit just right because the hem length is generally longer that is catered to taller men around 6′.

    Reply
    • Ian Chandler says

      January 2, 2024 at 5:05 pm

      This one’s from Tailor Store! I believe the exact style has been discontinued, but the current shirts should have the same fit. Might want to check out this article on brands for short guys, too 🙂

      Reply
      • John says

        January 2, 2024 at 5:24 pm

        Thank you so much for the response! Such a nice looking flannel too, but figured it would be discontinued since it’s been a few years since this article was posted. But I will definitely give Tailor Store a try since it looks like an amazing fit!

        Reply
  2. Pat says

    October 5, 2021 at 9:53 am

    Is made to measure still the only way to get a decent fitting flannel for shorter guys? Seems everywhere I look they are huge.

    Reply
    • Brock says

      October 5, 2021 at 9:57 am

      Some of the shorter guy brands have flannel button ups and work shirts – https://www.themodestman.com/best-places-to-buy-clothes-for-short-men/

      But custom isn’t a bad option either!

      Reply
  3. Fernando says

    February 25, 2017 at 12:38 am

    Hi Brock, quick side note, two weeks into watching your videos and reading your guides/blogs has started me on my journey. I used to just wear flannels (not the best looking ones either) and such for work and never cared about what I wore. Now I am ready to kick into gear and start looking better (on a budget). Thank you for all your help!

    Now to my question about this flannel, although the tailor store is really awesome, I have been looking for flannel shirts to style the way you have (specifically for the small square two color shirt) but have had zero luck finding any. Any suggestions on brands that have similar flannel patterns to the one you have?

    Reply
  4. gentlemanwithin says

    November 29, 2016 at 10:21 pm

    Great looking flannel shirt, Brock. Perfect color combination. Checked out their site. I love the customization options. The best preview I’ve ever seen.

    Reply
    • themodestman says

      November 30, 2016 at 11:36 am

      Yeah that preview is awesome. Loved your travel guide btw.

      Reply
  5. Oliveratom says

    November 29, 2016 at 7:10 pm

    Brock what is the best way for someone to take their measurements? or know the measurements for a shirt like this? Thank you for having this blog, you give really great advice for us shorter guys.

    Reply
    • themodestman says

      November 30, 2016 at 11:36 am

      It’s best to follow whatever instructions the brand you’re buying from provides. Most have slightly different measuring techniques. I like to use a combination of body and garment measurements (assuming that’s okay with the brand).

      Reply
  6. Simon Miles says

    November 29, 2016 at 7:00 pm

    I’ve been getting my shirts from Tailor Store for a while with great results, and can second this recommendation. Hardly more expensive than buying off the rack either, once you factor in the inevitable cost of sleeve shortening etc.

    Reply
    • themodestman says

      November 30, 2016 at 11:35 am

      Yeah it’s actually amazing how inexpensive they are, considering the fit and quality.

      Reply
  7. Brad says

    November 29, 2016 at 3:46 pm

    Great reminder of made-to-measure flannel. I stopped wearing them since they are usually made for people over 6 feet tall and 250 lbs. Checking out the site now. Flannel is so versatile in the fall/winter.

    Reply
    • themodestman says

      November 30, 2016 at 11:34 am

      Yeah man, most flannel is pretty big/baggy. MTM is a great option if you want flannel that actually fits.

      Reply
  8. The Old Professor says

    November 29, 2016 at 12:33 pm

    Best video yet. Thanks.

    Reply
    • Brock says

      November 29, 2016 at 12:34 pm

      Thank you!

      Reply

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