Every Good Way To Wear A Plaid Shirt

Men's Fashion

Contemporary thinking on plaid tends to lie in one of two camps: those who see it as a simple, stylish essential, and those who denounce it as a sartorial symbol of that shudder-inducing neologism, the ‘hipster’.

But to dismiss plaid as just another tired trend is to do it a disservice, as its history and longevity suggest otherwise. Whether it’s in the form of a classic flannel jacket, a preppy button-down shirt or subtly situated within a suit, we’re firmly planting our flag in the pro-plaid camp.

So what makes the plaid shirt so enduring? How do you wear it, and wear it well? If you’re unconvinced, let this be an easy-to-follow illustration of just how useful this wardrobe staple can be.


What Is Plaid?

Well, that’s more complicated than you might think. “Plaid” is sometimes used as a blanket term for all kinds of check shirt and it’s also mistaken for flannel (which is a fabric, not a pattern). In truth, plaid is a very specific pattern, and one you already know: tartan. (The confusion is deepened by the fact that in Scotland, the word also describes a specific traditional garment, but let’s move on.)

An incredibly wearable, flattering pattern, it’s a series of criss-crossed lines in two or more colours, and forms a grid of squares in myriad combinations. These days it’s intrinsically linked the great American outdoors, especially on shirts, but plaid was first a loaded political symbol.


Its origins lie back in the 1500s, deriving from Scottish tartans that represented rival clans battling for control in the Highlands. As a result of the Scottish rebellion, The Dress Act of 1746 banned plaid and tartan throughout Great Britain and wearing it was a punishable offence for over four decades.

When plaid eventually made its way across the pond to North America, it began to develop its connotations of outdoorsmen as cowboys, lumberjacks and hunters championed the plaid flannel shirt for its durability. US heritage brands like Woolrich and Pendleton soon spun their now-iconic two-tone Buffalo check styles.

It entered the annals of pop culture through a generation of mid-century film icons like James Dean and Rock Hudson, and made the big time when worn by The Beach Boys on the cover of their 1962 album Surfer Girl.

Kurt Cobain Performing

Fast-forward to the early 1990s and grunge consolidates the pattern’s cool factor, with seminal bands like Nirvana and Pearl Jam and groundbreaking designers like Alexander McQueen all offering their takes on the check. Most recently, hip-hope has co-opted elements of grunge style with artists like Travis Scott wearing plaid shirts on stage.

From Scottish clans to modern subcultures, plaid is a high-low cultural symbol that’s simultaneously alternative and normative, adopted by both the counter-culture and the mainstream.

Steve Sanderson, founder of Manchester-based menswear emporium Oi Polloi, locates plaid’s appeal in the sheer variety of pieces available, from jackets to shirts to scarves: “There are so many varied versions around – pretty much every man can find one that’s right for them.” But, as with most things in menswear, it’s the classics that really resonate – like the original plaid shirt.

Tommy HilfigerTommy Hilfiger

How To Wear A Plaid Shirt

From its outdoor origins at Woolrich to contemporary high fashion advocates such as Hedi Slimane at Saint Laurent – who does a great lived-in plaid, if you’re willing to pay for the privilege – plaid’s versatility has been used as a starting point for alteration, experimentation and innovation, finding itself put across ties, coats, jackets, trousers and even underwear.

Aesthetically speaking, plaid shirts in most colour schemes are low-risk, sitting nicely atop a pair of chinos or jeans, and equally at home under macs or technical jackets or worn unbuttoned over a classic white T-shirt.

As with most patterns, the key to embedding plaid into your outfit is to keep the rest of it pared back; plaid’s a bold, colourful pattern so let it do most of the work and look to style it with neutral colours that complement your shirt’s palette.

In fact, this type of shirt is the ideal solution for guys who are keen to introduce a little more visual interest to their casual looks but are unsure how to go about it.

How To Wear A Plaid Shirt

mango man scotch & soda uniqlo zara

The Best Brands For Plaid Shirt

Carhartt WIP

The story of Carhartt WIP is one of two tales. There’s the workwear made by a family-run business and founded in the 19th century, and then there’s the subtle shift into streetwear territories in the ‘90s that saw the brand come out the other side as a global player in the world of style.

Both sensibilities are at play in its plaid shirts, that come in a busy, eye-boggling check while still maintaining the thick, cotton construction that has made them a hard-wearing favourite for so long.

Buy Now: £70.00

L/S Linville Shirt


In the home of grunge, Seattle, you’ll also find Filson, an outerwear brand that has made perfecting the staple plaid shirt its mission.

The design is more lumberjack than Celtic kilt, but there’s elevating touches from the band of gold in its red plaid to the ultra-thick and comfy brushed twill and the double-needle stitching around the seams, which takes longer but makes for a sturdier shirt at the end of it – no grungy frayed edges here.

Buy Now: £155.00


Ralph Lauren

Along with its polo shirts, the cotton-button down is one of the jewels in the crown of preppy fashion pioneer Ralph Lauren. The plaid shirt isn’t a million miles away, with the label maintaining that same, flattering slim fit that hugs the shoulders and puffs out your chest like Superman.

Differences come in the washed and weathered effect on the shirt, heavier, hard-wearing cotton and a western shoulder yoke that screams rodeo cowboy. These plaid shirts are made for walking, you see, and that’s just what they’ll do.

Buy Now: £185.00


Beams Plus

The style at the in-house brand of Japanese department store Beams is a novel fusion of centuries-old Americana and the contemporary, genre-bending style of its homeland.

This magic potion makes for a real neat take on the plaid shirt, with a restrained check, a boxy fit at the shoulders and a nifty, contrasting pattern on the occasional patch pockets.

Buy Now: £189.00



A prominent member of sustainability non-profit, Better Cotton Initiative, H&M is one of the best places to shop on the high street if you’re looking for something affordable but don’t want to pay the extra with your conscience.

There’s no poly-cotton blend here then, all 100 per cent cotton flannel shirts, which can be taken back to the store for recycling once worn out along with a solid range of styles to choose from, as you’d expect from the high street.

Buy Now: £17.99

h&m Cotton flannel shirt


Originally just a single mill in a sleepy town in Pennsylvania, Woolrich has certainly expanded its fabric expertise down its 190 years.

Wool is still the stand-out but that quality can be felt in its cotton plaid shirts, cut in a classic fit and with a box pleat on the back to smarten up proceedings. Dual patch pockets then sidle the shirt into more workwear territories before a stunning, multi-toned check finishes the job.

Buy Now: £150.00

Hunting Flannel Shirt

Alex Mill

The brainchild of former J. Crew employees, Alex Mill is as blissfully simple-to-wear as its founder’s former haunt.
There is a stronger workwear influence than the preppy purveyor though, which you can see in its plaid shirt.

A completely new and unique pattern grabs the attention, the result of its design teams travels around the Pacific North-west, while an ever-so-slightly over-sized fit makes it perfect for layering over a tee underneath.

Buy Now: £110.00

ALEX MILL Checked Cotton-Flannel Shirt


Outerwear giant and raging eco-warrior Patagonia has built up a reputation as one of the most likeable and sustainable brands in the world. The impressive environmental agenda helps – all organic cotton and a sterling, for-life recycling program – as do the ever-wearable pieces it sells.

When it comes to the plaid shirt there is an impressive range of checks and colours on offer set on a mid-weight flannel that keeps things smart, but relaxed, so you can keep your mind on other things. Like, saving the world.

Buy Now: £75.00

Patagonia Men's Long-Sleeved Lightweight Fjord Flannel Shirt


Well-designed with some of the best fabrics around and all cut in a comfortable fit, Japanese brand Uniqlo, has risen up the high street food chain, less for its affordable pricing, and more for just being really good.

Expect the same in its plaid shirts, made in flannel that has been triple brushed on the inside. This raises the cotton fibres so it almost feels like wearing a fleece.

Buy Now: £24.90


Gitman Vintage

As opposed to other specialised shirtmakers that focus on more formal dress shirts, Gitman Vintage is all about creating casual shirts that feel lived-in.

Vintage styles are a speciality, the plaid shirt firmly slotting into the category. The Gitman style comes with a peaked shoulder yoke, that feels subtle, not overdone, and a premium combed cotton – pretty much the gold standard when it comes to the fabric.

Buy Now: $220.00

California Triple Yarn Button Western


Along with the Gucci stripes and the Louis Vuitton monogram, the Burberry check is one of the most recognisable patterns in fashion history. Well, when you’ve spent this much on a shirt, you’ll want people to know.

Kept crisp and clean in cut, design, and pattern, the Burberry check shirt is a designer shirt more versatile than it might first seem, able to seamlessly fit into a relaxed tailoring look, unlike most of the other options on this list.

Buy Now: £270.00

Check Cotton Poplin Shirt


Traditional pieces given a streetwear edge has made surfwear brand Stüssy one of the most in-demand labels in the world at this minute.

Its plaid shirt selection is different from the plaid shirt you know in every way but name. Checks are given a scuzzy, bleached effect, while a wool blend is used instead of cotton, with a crop around the waist and zip-front that edges it more towards the blouson jacket than anything Kurt Cobain would have thrashed around the stage in.

Buy Now: £140.00


J. Crew

Having made its name a little later than its preppy rivals, J. Crew offers a modern, easy-to-wear take on that timeless, collegiate style.

And your tutor won’t kick you out of the lecture hall if you rock up late in one of these neat plaid shirts with a flattering, tailored fit, and a cotton brushed on both sides, that means you’ll keep comfy, even if you’re forced to sit at the front of class.

Buy Now: £89.00

Slim midweight flannel shirt in orange plaid

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