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A Man’s Guide to Styling Flannel

Zach sitting on bench wearing red Portuguese flannel shirt, Corneliani ink navy vest, and frame fade to grey jeans

We all know that a flannel shirt is a staple when it comes to casual men’s style. It’s masculine, it’s comfortable, and it’s a classic look that has stood the test of time. 

While we’ve got nothing against the lumberjack look, there are more ways to style flannel than just “farmer-chic.” We suggest having a few options in your closet to allow you to roll out a handful of looks: 

  • One or two solid colours, like navy or mustard. Solids are the easiest to layer and dress either up or down.
  • A dark, smaller check, which is a little on the dressier side.
  • A classic red or green plaid to stay true to the flannel roots.
  • A lighter, larger check with white or cream mixed in to balance out the darker pieces in your wardrobe.
  • At least one slim fit shirt and one in a larger size, so you can layer under or over other clothing.

Once you’ve got a few different options in your closet, it’s just a matter of putting the pieces together properly. Here are five of our favourite ways to style a flannel shirt. 

5 Ways to Style a Flannel Shirt

1. Over a hoodie

flat lay image of olive alex mill hoodie, grey toque, zegna metal aviator sunglasses, frame finn light wash jeans, brunello cucinelli grey suede sneakers, and red and purple check portuguese flannel shirt

Size up your flannel shirt and treat it like an outerwear piece. You can wear it over any knitwear, but it’s a particularly rugged way to make a basic hoodie more interesting. Light wash jeans and sneakers are a no-brainer with this look. 

Shop the look:

Olive hoodie | Studio check flannel shirtLight wash jeansGrey suede sneakers | Grey hat | Aviator sunglasses

2. As a middle layer

Flat lay image of ralph lauren polo jeans, bronze APC bomber, cream and red portuguese flannel shirt, and blue henley shirt

The great thing about flannel is that you can add texture and pattern to your outfit without looking like you’re trying too hard. By wearing a flannel shirt as a middle layer, you aren’t being too showy, but you are elevating your look above just a basic tee. Wear your flannel over a henley or t-shirt, and under a bomber jacket. It’s stylish but still casual and comfortable. 

Shop the look:

Bronze bomber jacket | Coachella check flannel shirt | Blue henley shirt | Distressed jeans | Black gloves | Tortoise shell sunglassesGunmetal Danner boots

3. As a pop of colour

Flat lay image of olive corduroy trousers, brown boots, grey sweater with mustard portuguese flannel shirt under, and a green toque

A clean crew-neck sweater is a great canvas for your flannel shirts. Add a pop of colour to your sweaters by layering bold flannel underneath, and wear it with casual trousers like corduroy or chinos. A solid colour like this mustard hue is great for evening outings, but you can also go with a plaid flannel shirt for a more casual daytime look. 

Shop the look:

Grey crew neck sweater | Yellow flannel shirt | Olive corduroy trousers | Green hat | Lace up boots

4. Under a sport jacket

Flat lay photo of navy trousers, brown loafers, light blue portuguese flannel shirt, textured brown sport jacket, and black zegna wallet

This is a look that needs to be pulled off carefully.  Select a sport jacket that is on the casual side. Something with a soft shoulder, patch pockets, and an easygoing fabric is ideal. Lighter colours and textured fabric also tend to be on the more casual side. A solid coloured flannel shirt is also the easiest look to pull off here, but a dark, smaller check would also work. Wear it with easygoing cotton trousers or chinos. A loafer or oxford shoe with a chunky rubber sole works well to tie the casual/chic look together. 

Shop the look:

Brown sport jacket | Blue flannel shirt | Navy cotton trousers | Rust pocket square | Black phone walletBrown loafers

5. As a refined statement piece 

Red flannel is a classic, but if you’re not careful, you can easily slip into lumberjack territory here. Layer a sleek vest overtop to dress it up a little bit, while still allowing the shirt to stand out. This works well with green plaid flannel as well. Dark jeans and boots work best to keep it looking refined. 

Shop the look:

Ink navy vest | Red check flannel shirt | Dark grey jeans | Dark grey hiking boots


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