How to Wear a Flannel Shirt | Tailor Store Review

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

Read on to learn how a flannel shirt should fit and what makes it casual. Plus, see three example outfits from my own wardrobe.

How to wear a flannel shirt

Note: Big thanks to Tailor Store for making this post possible! Tailor Store sells custom shirts from $69. you can design your own from scratch or choose from their collections. Use the code MODESTMAN20 for 20% off your order.

Okay, first we'll talk about how a flannel button up should fit. Then we'll go over the little details that make a casual button up different from a dress shirt.

Finally, I'll show you three ways to wear a flannel shirt using examples from my own wardrobe.

How a Flannel Shirt Should Fit

A flannel button up shirt should fit just like any other casual button up shirt, although I think 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.

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

How a flannel shirt should fit

#1: Shoulder seam should sit where arm meets shoulder (without hanging past that point)

#2: Collar should button comfortably without being too tight (room for one finger)

#3: Length shouldn't go past bottom of fly when worn untucked

#4: Sleeves should hit your wrist but not go past it

These are just guidelines, so don't get too hung up the specifics. For example, if you never wear a tie, it's okay if you're collar is a little too tight to be buttoned comfortably.

That said, if you're buying a custom shirt, you should be able to achieve a near perfect fit.

Casual Details

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

The great thing about buying made-measure is the fact that you can customize these details.

Casual button down details

#1: Hem is straight or slightly curved (no deep “wings” like a dress shirt that's meant to always be tucked)

#2: Cuffs are short and soft (no stiff interfacing)

#3: Collar length is short and soft (no stiff interfacing)

It's also important for shorter men to opt for shorter cuffs and collars. This means, no matter what style your collar is (button down, point, club, spread, etc.), the point length should be short.

Same goes for sleeve cuffs. No matter what style they are (single button, double button, rounded, etc.), it's best if they're on the shorter side.

3 Ways to Wear a Flannel Shirt

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.

Here are three ways to wear a flannel shirt:

Flannel shirt outfits

Outfit #1: Lumbersexual with a Twist (shirt | jeans | boots | watch | shades)

This is your classic “jeans and boots” flannel shirt getup, but it's much different than the classic lumberjack look, mostly because of the color palette. The dark blue, grey and black is a pretty edgy color combo that will definitely set you apart from the crowd.

Outfit #2: Office to Happy Hour (shirt | sweater | chinos | boots | glasses)

You can still wear casual flannel shirts to the office. Just throw on a v-neck sweater or quarter zip pullover and you're good to go. You could swap in whatever shoes you like – wingtips, loafers – but you know I love the chukkas!

Outfit #3: My Fall Uniform (shirt | vest | jacket | jeans | boots)

This is basically my fall uniform – jeans, causal button up, light vest, light jacket and of course, boots. If it's colder, I'll just throw on a heavier jacket. It's it's not too cold, I'll ditch the jacket altogether. If I had to pick one outfit to wear for the rest of my life, it would be this one.

About Tailor Store

I've reviewed a lot of custom clothing companies, both good and bad, and it's my opinion that Tailor Store is one of the best.

Here's why:

Tailor Store shirt designer

Tailor Store shirt designer

They have a perfect fit guarantee. If your first shirt doesn't fit, you send them pictures, they diagnose the problems and send you a new one.

I took them up on this, as my first shirt wasn't quite perfect. They didn't ask me for extra measurements or to take it to a tailor. They just sent me another one, and it fit wonderfully.

They're online Shirt Designer is second to none. Mostly due to the real-tim 3d modeling, it's the best user interface I've come across in the online made-to-measure world.

They offer countless customizations – more than most other brands – which is crucial for men with non-average builds.

They respect their employees and the environment. Tailor Store is dedicated to providing their tailors with good working conditions, and they've gone 100% carbon neutral.

In a world where cutting corners to increase profits is the norm, it's refreshing to see an organization doing everything they can to remain ethical.

If you want to try Tailor Store for yourself, use the code MODESTMAN20 for 20% off your order.

Questions? Comments? Leave a comment below!

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  1. The Old Professor says:

    Best video yet. Thanks.

  2. 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.

  3. Simon Miles says:

    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.

  4. Oliveratom says:

    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.

    • themodestman says:

      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).

  5. gentlemanwithin says:

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

  6. 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?

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