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 does one 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.

Origins Of The Plaid Shirt

Before it became intrinsically linked with the great American outdoors, plaid was a loaded political symbol. This humble casual shirt’s beginnings stretch back to 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 and US heritage brands like Woolrich and Pendleton 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.

Fast-forward to the early 1990s and grunge’s cultural takeover 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. From Scottish clans to subcultures, plaid is a high-low cultural symbol that’s simultaneously alternative and normative, adopted by both the counter-culture and the mainstream.

“It’s this combination of classicism and ‘cool’ that has seen the humble plaid shirt endure, and it’s why we still champion it,” says Luke Raymond, Menswear Fashion Editor at

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.

How To Wear

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 – to success at global retailers like ASOS, 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 a Harrington jacket or worn unbuttoned over a classic white crew neck 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.

Indeed, a plaid 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: “[For] menswear consumers who generally ‘buy less but buy better’, plaid is an enduring fail-safe – always fashionable but never trend-chasing,” says Raymond.

Casual Outfit Inspiration

Men's Plaid Shirts - Casual and Smart-Casual Outfit Inspiration Lookbook

j.crew autumn 2013j.crew aw15baldwin aw15crew clothing aw15el ganso ss15j.crew september 2015forever 21 aw14falconnable 2015avva aw14primark aw14burton aw14ay not dead aw15

Smart Outfit Inspiration

Men's Plaid Shirts - Smart Outfit Inspiration Lookbook

j.crew September 2015t.m. lewin ss15mj bale aw15banana republic aw13massimo dutti march 2014faconnable 2015gant 2014aquascutum ss16mango man aw12suitsupply 2015calibre summer 2013

What To Look Out For

When on the lookout for the right plaid shirt, Raymond recommends focusing on fit, colour and a certain level of authenticity. “A plaid shirt can’t be too heavy, nor too stiff, and it needs to have been, or at least appear to have been, worn,” he says.

So despite having plenty of fresh options to choose from both at the high and low ends of the market, it’s worth rifling through a few vintage shops first, as they’re often home to some of the best plaid offerings.

Cotton Flannel

If buying new, start with flannel and workerwear shirts – the plaid world’s most versatile and durable mainstays.

For premium quality at less-than-luxury prices, look towards American revisionist brands out of Japan like Beams Plus. The Tokyo-based label’s nostalgic reworking of old-school classics results in some of the finest menswear around.

Another is Engineered Garments, a New York-based company with a similar ethos to Beams Plus. The red and navy brushed plaid work shirt from Engineered Garments and the Black Watch button-down flannel from Beams will cost you a bit, but the fit and feel of both is top-notch and they’re built to last.

At the other end of the price spectrum, both River Island and Uniqlo offer great value flannel plaid shirts in a wide variety of colourways, so you’re bound to find something that suits.

Men's Plaid Cotton Flannel Shirts


Wool Flannel

Norse Projects, the Danish menswear brand that uses its home country’s weather as a starting point for its collections, offers a more traditional style in its Anton wool plaid shirt. And if it’s decades-old authenticity you’re after, a wool flannel style from Woolrich or Pendelton is always a great choice.

Team them with straight-leg jeans, slim cords or camel chinos, a denim jacket and a pair of classic Red Wing boots to achieve the full Americana effect.

If you don’t want to break the bank to get this style, Urban Renewal – Urban Outfitters’ in-house line of re-worked vintage finds – stocks an array of plaid options. Throw one of these over a crisp white T-shirt and team with a white plimsoll or leather sneaker for a laid-back look that’s far from sloppy.

Men's Plaid Wool Flannel Shirts


Lightweight Alternatives

Lighter weight plaid shirts – crafted from breathable Oxford cloth – are not only a better bet for warmer days, they’re also a touch smarter, lending your look more of a preppy, rather than punk, vibe.

All-American brands should be your first port of call for this type of shirt, with the likes of J.Crew and Ralph Lauren offering a wide variety of styles year-round.

Men's Plaid Oxford Shirts

Ben Sherman Oxford Shirt with Multi CheckJ.CREW VINTAGE OXFORD SHIRT IN BUFFALO CHECKM&S Collection Tailored Fit Long Sleeve Oxford Checked ShirtPOLO RALPH LAUREN MEN'S BUTTON DOWN CHECKED SHIRT

Final Word

The broad, cross-demographic appeal of the plaid shirt has allowed it to straddle all ends of fashion, particularly giving risk-averse men a chance to experiment – even if only slightly – with their day-to-day style. “Plaid shirts are a subtle way to introduce print and colour to a menswear wardrobe dominated by neutral tones and plain surfaces,” says Raymond.

But it’s also the plaid shirt’s relative simplicity – as compared to many modern-day trends in menswear – that connects it to the core values of men’s style. As Sanderson best puts it: “Men’s clothing doesn’t, and shouldn’t, need to change too much, but it should always evolve.”

How do you feel about the plaid shirt? What are your favourite versions and what do you like to wear it with?

Comment below to let us know.