Thanks to the Olsen Twins and It Girls in Europe, Everyone is Suddenly Shopping This 30-Year-Old Shirt Trend for Winter
To be in the know in fashion is to be acutely aware of the fickle way trends fall subject to the passing of time. This is at least true in the case of the best flannel shirts—a style of top that was once exclusive to lumberjack types and field ranchers before breaking through to the mainstream courtesy of endorsements from Nirvana frontman Kurt Cobain and Claire Danes in My So Called Life.
Ask anyone who grew up in the ‘90s, and they’ll tell you that plaid button-downs weren’t the quiet luxury dog whistle they’re revered as now. Now, with flannel shirts dominating runways, gaining co-signs from the celebrity style set and being rendered in expensive-looking high-street variations, how did they go from grunge staple to the pinnacle of sophistication?
But first, a little history. The origins of modern flannel shirts, as we know them, trace back to 17th-century Celtic communities in Scotland and Wales. With tartan fabrics being a historically rich and culturally relevant print in these spheres, flannel offered a slightly modern interpretation thanks to the lighter wool weave. (Although it was still incredibly heavy-duty to keep up with the extreme climate demands.)
Crossing over to the US amid the Civil War, as the garment served as undershirts for military regalia, it would only take another hundred years for the style to reach the masses during the heroin chic era of the late 20th century. During this decade, flannel balanced two sides of the style spectrum—a bourgeoisie, buttoned-up and preppy style epitomised by Cher Horowitz’s iconic yellow skirt suit, or the anti-establishment and alternative aesthetic pioneered by bands like Pearl Jam and Soundgarden.
What is the Flannel Shirt Trend?Thanks to some tactical endorsements by the luxury set, the best flannel shirts have shed these connotations. Instead, they’re now held up as a beacon of minimalist taste and refined sensibility. The first sign that the flannel shirt trend would skyrocket came when Kate Moss wore a trompe-l'œil leather iteration on Bottega Veneta’s spring/summer 2023 runway.
Then, Mary-Kate and Ashley Olsen further cemented the style’s relevance in The Row’s spring 2025 collection, with the first look from the range a bold declaration that, whether you like it or not, flannel shirts are now cool. That’s the power of the brand’s adherents—whether it’s a pair of jelly sandals, grosgrain ribbon flip-flops or an ornamental orange towel, its customers will lap it up.
Of course, to the average shopper, it may come as a surprise to suddenly see that something you could easily purchase at any Primark be given the designer treatment and rendered with an exorbitant price tag. Still, it's in the way that these industry titans subvert notions of what can and can’t be deemed elegant that has further propelled the piece’s appeal within fashion circles.
That being said, wearing one of the best flannel shirts doesn’t have to be this disruptive style choice that these brands have positioned it as. (Though the style’s early adopters, like Marc Jacobs during his Perry Ellis tenure, certainly would take great pleasure in knowing that this nonconforming silhouette has become conventionally accepted as elegant.)
Knowing the backstory about how this trend came to be is only half the story. The other is being written now, through all the contemporary street style offerings, cementing the best flannel shirts as a trending item that can elevate everything from pencil skirts to woollen trousers.
Versatile, unfussy and easy to layer, keep scrolling through for the 21 best flannel shirts to shop in 2025, plus everything you need to know about styling in a way that’s less nostalgic and more modern.
When looking for the best flannel shirts, it's important to consider the fabric composition of the piece. As the style is traditionally made of wool, the shape has historically always been suited for cooler climates, which makes warming options made with natural fibres the superlative choice.
There are so many incredible options available that feature 100% cotton, including the viral check COS style, a chic collarless red iteration from Dôen and a gorgeous tailored style from Burberry.
Given the deep-rooted languid shape that flannel shirts possess, keeping your overall ensemble roughly casual is the easiest way to style them. Think: Straight-leg jeans, asymmetrical linen skirts, like the ones Faithfull The Brand does so well, boxy leather jackets and even corduroy trousers. (On the latter, the viral M&S option and pieces from small brands like Friends with Frank are fab choices!)
Style Notes: Bottega Veneta's spring/summer 2023 runway.
Style Notes: Burberry's autumn/winter 2025 runway.
Style Notes: Isabel Marant's autumn/winter 2025 runway.
Style Notes: Dior's Resort 2025 runway.
Style Notes: Kallmeyer's spring/summer 2025 runway.
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