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 shirts 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 for men 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 and what the best plaid shirts for men are.

J.Crew

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 crisscrossed 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.

J.Crew

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.