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When you think of flannel, the humble plaid shirt usually comes to mind. The word “flannel” though, refers to the soft wool or cotton fabric designed in a range of prints and patterns (not just plaid) — and these days, the popular checked button-down is one of the most versatile pieces out there.
Just like the cardigan, the plaid garment’s story begins centuries ago in Europe. The material originated in Wales, where it was spun from the sheep-rich country’s plentiful supply of wool, and rubbed with a fine metal brush to create a texture that was soft and warm enough to wear in the winter. Mass production during the Industrial Revolution brought the already affordable silhouette to even more people, and it eventually hopped across the pond to America’s chilliest west coast states.
Over in the Pacific Northwest, British weaver Thomas Kay landed in Oregon, where his grandsons would eventually establish Pendleton Woolen Mills in the early 1900s. The company’s wool shirting debuted in the early Twenties and transformed from a working-class wardrobe essential to an outdoorsman staple and symbol of American leisure.
It wasn’t until the Sixties that the blue collar piece was associated with rock music. The Majorettes name-checked Pendleton in their 1963 hit, “White Levis,” and soon after, a burgeoning surf-rock band called the Pendletones would pair the heritage company’s plaid button-downs with tees and khaki shorts. (The band changed their name of course, to The Beach Boys.)
Flannel shirts continued to enjoy regular rotation among the citizens of Seattle and Portland, home to seminal grunge bands like Nirvana, Hole, Pearl Jam, and Soundgarden. Thrift-store chic was synonymous with Nineties, and the era ushered in a new way to sport the checked shirts, as seen on concert stages and fashion runways alike.
Though it’s often associated with grunge, the workwear garment also transcended music genres. Alongside rock icons like Kurt Cobain, Courtney Love, Eddie Vedder, and Chris Cornell, flannel was also a hit in hop hop, as seen on the members of N.W.A., TLC’s T-Boz, Aaliyah, and Missy Elliott, to name a few. And let’s not forget Nashville: You’d be hard-pressed to find a country musician who hasn’t suited up in a cozy flannel shirt.
Today, the classic cold-weather button-down has universal appeal — it looks good regardless of your own personal style, and you don’t have to be a chart-topping musician to pull off the look. Of course, there’s no shortage of flannel-wearing stars to look to for sartorial inspiration, including Kanye West, A$AP Rocky, Justin Bieber, and John Mayer to just name a few.
What Are the Best Flannel Shirts?
The best flannel shirts depend on the look you’re going for. They can easily channel grunge nonchalance when worn with ripped denim and sneakers, or take you from basic Paul Bunyan to effortless PNW-cool with black jeans and boots. The trusted button-down also translates well in professional settings, depending on the pattern and silhouette. We’ve rounded up some of the coolest plaid flannel shirts no matter where you’re headed — check out our top picks below.
1. Eddie Bauer x Sub Pop Flannel Shirt
Sub Pop Records was the originator of Seattle’s grunge scene, and Eddie Bauer is a wardrobe staple of outdoorsy adventurers in the Emerald City and beyond since it was founded in 1920. It’s a wonder that the two Washington-born brands only recently joined forces on this classic fit flannel shirt, which boasts a vintage look and was designed to resist pilling. It’s available in a range of colors and patterns.
2/ John Elliott Hemi Plaid Flannel Raw Hem Button-Up Shirt
Los Angeles-based streetwear designer John Elliott puts a California-luxe spin on the flannel silhouette. Whether it’s worn open or buttoned up, this slightly oversized shirt features a front chest pocket and a frayed hem that brings an understated edginess to any look.
3. Outerknown Transitional Flannel
Eco-conscious label Outerknown’s flannel shirt is made of soft, brushed organic cotton that feels as comfy as cashmere. This button-down has a classic fit and is available in a variety of colorways.
4. Pendleton Board Plaid Lined Wool Button-Up Shirt
For that Beach Boys-inspired vintage aesthetic, you’ll want to throw on Pendleton’s iconic Board flannel button-down. It’s made from Oregon-sourced Umatilla virgin wool fabric that’s water-, stain-, and odor-resistant, so it’s great for the beach or hiking trails.
5. Off-White Checkered Flannel Shirt
Leave it to luxe streetwear label Off-White to turn this reliable garment into an effortlessly cool street style piece that makes a subtle statement. This button-down shirt features creative director Virgil Abloh’s signature European tailoring with a modern take on the traditional plaid pattern. It’s finished with two large chest pockets.
6. Faherty Stretch Sweaview Flannel Shirt
This pastel plaid flannel shirt by New York-based Faherty strikes the perfect balance between buttoned-up prep and coastal-cool. It’s made of lightweight cotton and looks great at the office with slacks and a casual blazer, and on weekends with jeans and Chuck Taylors.
7. Brixton Bowery Flannel Shirt
Southern California-based Brixton is rooted in music and skate culture, and the brand’s plaid green Bowery flannel shirt is great for looking casually cool. It’s got a standard fit and a curved hem, and button-flap chest pockets add a cool blue-collar touch.
8. United By Blue Men’s Responsible Flannel
Sustainable label United By Blue’s best-selling flannel shirt is made of a blend of organic cotton and recycled polyester. It features a shirttail hemline, box pleats on the back, and two button flap pockets on the front, making it versatile for work and casual settings.