How to Wear a Flannel Shirt in 5 Modern Ways

You have plenty of options.

After a few years in the fashion wilderness, the last couple of years has seen flannel shirts rapidly gain in prominence. They’ve gone from the butt of every hipster joke (Why did the hipster wear flannel in the summer? He wore flannel before it was cool) to a piece that suddenly seems fresh and exciting.

This is something I can definitely get behind. These shirts are practical, warm, and casual, and really easy to pull off. They’re great in spring and fall during the time when it’s too cold for a t-shirt but too warm for a sweater. And they serve as a warm layering piece during the winter.

Hold On, What Exactly is a Flannel Shirt?

Flannel shirts can technically be any shirt made from the material flannel. For the sake of this article, when I say flannel I’m talking about what I assume most of us think of when we hear the word: thick casual shirts with (often loud and colorful) check patterns.

What to Wear With a Flannel Shirt?

Flannel shirts are casual, warm, and mostly worn in fall, winter, and spring. This pretty much defines what you wear with your flannel shirt—look for other items that are casual and warm.

I think the best pieces that go with flannel shirts are:

  • Jeans: Especially dark or raw denim.
  • Chinos: Neutral shades work well.
  • Chunky knits: These are casual, warm, and suit the flannel vibe perfectly.
  • Boots: See the point above. The more rugged the better.
  • Denim jackets: Denim and flannel and a perfect match.
  • Sneakers: More casual footwear. I think my black Vans go great with my flannel shirt.
  • T-Shirts: Wearing a t-shirt under a flannel shirt is a popular way to style these items.

How to Wear a Flannel Shirt: 5 Stylish Outfits

Flannel Shirt with Jeans and Boots

Flannel shirt dark jeans
The Brdwlk

This is the simplest way to wear a flannel shirt. Simply pair it with your favorite jeans and some rugged boots. The type of jeans doesn’t matter too much. I think it looks great with both skinny jeans and wider fits. My shirt is quite dark, so I like to wear it with dark denim. If yours is lighter it will look just as good with light blue jeans.

Wear Open Over a T-Shirt

Flannel shirt over t-shirt chinos
The Brdwlk

Flannel is thick which means it can work well as an outer layer. It’s perfect for times when it’s too warm for a jacket but you want an extra layer. Flannel shirts typically have a lot going on, so balance this out by going for a plain t-shirt. The best color for your outfit will depend on the color of shirt, but gray, navy, and white are safe bets that many of us have in our wardrobe already.

With a Denim Jacket and Boots

Flannel Shirt Denim Jacket Jeans Boots
The Brdwlk

Denim jackets and boots are both items that suit the rugged vibe of flannel shirts perfectly. This works well when worn with jeans or chinos. I like to wear this combination with chunky worker-style boots or desert boots. More formal boots don’t look as good. I have a pair of black Chelsea boots and they don’t work in this type of outfit. My black denim jacket works with dark blue jeans and boots. But I think pretty much any color would work, depending on the color of your shirt.

Under a Thick Sweater

Flannel Shirt Sweater Jeans
The Brdwlk

I love wearing my flannel shirt under a sweater for two reasons. The first is because it’s super warm. This pairing is enough to get me through the coldest days. And second is because I like how the check pattern catches the eye at the color and around the wrists. I think this looks best thick, plain sweaters. A patterned sweater with a check shirt might be too much for many outfits. Cardigans also work when worn over a flannel shirt.

With Chinos and Sneakers

Flannel Shirt Chinos Vans
The Brdwlk

While most of my flannel shirt outfits are with jeans, I think they also go well with chinos. The beige chinos in the above outfit suit the shirt and jacket well. But different color chinos will work with different color shirts. And the canvas shoes give the outfit a casual weekend vibe. I also think that you could easily swap out the denim jacket in this image for another type of casual jacket. For example, an overshirt or a leather jacket.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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