How to wear a flannel shirt without looking like a cowboy

WE’RE IN AN AGE of symbolic dressing. If you consider how trends have been dictated the past few years, they’re founded on certain pieces and styles to easily adopt a ‘-core’. It’s what’s made ‘quiet luxury’ such a commercial hit with the how accessible it is. Because more often than not, you already have these pieces sitting somewhere in your closet.

The flannel shirt exists in this paradigm. Its plaid pattern has found renewed air for trans-seasonal weather layering. With its varied colours, it’s a more interesting top layer visually than the chore jackets that have dominated of late. And in its ubiquity, the flannel shirt is an easy way to play with colour, too.

But we’re moving past flannel’s streetwear neo-grunge of the mid-2010s, and back towards its origins on ranches and in surfing communities. In other words, people are dressing more literally; it’s why we can’t delineate between fashion re-editions of football shoes from ones you’d wear on the field. What flannel presents, then, is that it’s cruising the wave of Western wear. You could’ve stepped right off the ranch, and that’s not a bad thing.

So, if you’re thinking of rummaging to the bottom of your closet, here are some ways of wearing flannel in 2025.

The flannel shirt as a ‘shacket’

Wearing flannel as an overshirt is a no-brainer for trans-seasonal weather. It’s thick enough to layer on but light enough to pack away by noon. As a top layer, a flannel ‘shacket’, the plaid pattern adds more visually to a T-shirt and jeans than a chore jacket or an undone button-up, so consider colour: you can let your flannel speak over the neutral base.

There was a time in the mid-2010s, long before his dad makeover and courthouse style era, when A$AP Rocky would wear his flannel shirt to dinner. Seen on the streets of Los Angeles, the rapper paired his ‘flanno’ (as we say Down Under) with a graphic T-shirt and Palm Angels track pants. Though notice how the blue undertones in the flannel are highlighted with the complimenting purple bottoms and blue graphics. Take this page out his style book.

Think comfort in sizing

Comfort is the idea when wearing a flannel shirt, so it should sit looser, even boxier and a bit oversized on the body. The tyrannical tight shirt if for the office, but do yourself a favour a relax in a looser shirt. This is also a time to consider standard sizing, in which case size up from your usual.

Some brands and designers already understand the looser fit is a given for the style, so they’ve cut their flannel shirts intentionally oversized. In which case your normal size, and in some cases sizing down, is the go. The looser, oversized fit speak to one truth: the most common way to wear flannel is as an overshirt. So why squeeze yourself into it?

Flannel keeps tailoring casual

Flannel is a classic piece of Americana that connotes a different lifestyle to your reality, like urbanites wearing Salomons on their coffee run. In the popular imagination, the shirt gives a ranch-hand, working man type image. If this isn’t how you’d like to present yourself, scramble this signal with some tailoring. Consider it more for casual occasions, so not with a full suit but instead with a sports jacket and jeans, for example. What you’re aiming for visually is for the plaid pattern be the pop, and the colour can be secondary.

Go full yee-haw

All things Western was the prevailing trend of last year. Chalk it up the social upheaval in the United States, the American in Paris that is Pharrell Williams designing menswear at Louis Vuitton, or Beyoncé’s Cowboy Carter album, but these high-level creative outputs have trickled down into a desire for permanency provided in Americana. Flannel shirts are part of this too.

This is all to say that there hasn’t been a better time to own dressing like a cowboy. Starting small, a pair of dark wash jeans are the natural pairing with a flannel shirt, whatever the colours. A step further and you’re wearing boots (R.M. Craftsmans will acclimatise the look for Australia). Going full yee-haw? That’ll be a cowboy hat and proper cowboy boots.

Speaking streetwear

If the cowboy life isn’t for you, streetwear items offer another avenue of wearing the flannel shirt. Look to guys who’ve spun the look for not the ranch but for the coffee shop. Aspirational dads have been looking to actor Bradley Cooper for his style for years, but his treatment of flannel has been a staple. With a pair of joggers or cargo pants, the father of one makes it endlessly cool to wear with a pair of Air Jordan Max’s too.

Consider monochrome layering

Monochrome outfits turn some people off because you can risk looking like a walking Pantone shade. Prints are a simple way to break up this visual; they add dimension. They need not be bold either, if you don’t want to scare people by going full leopard print (which itself should be considered a neutral, by the way).

Remember that flannels feature complimenting colours – an instant failsafe. But its the secondary colour that you should pay attention to; to build the other garments around that shade to highlight it, letting the primary be the pop. Consider this look from the recent runway of Japanese label Auralee, where the lines of green in the flannel inform the olive trousers and remixed puffer-barn jacket; the dark blue is the pop.

You could leave it there, but to bring it one step further with a middle layer (in the designer’s example, the puffer), the colour should be the literal mix. Imagine you’re in art class and swirling green and blue to make a mint/teal shade. Visually, leave this bright flourish sandwiched in the blankness of the monochrome.

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