A way to make a statement without being a loudmouth? Check. A way to add impetus to an autumn/winter outfit without getting ahead of yourself? Check. The trouser that’s going to make all the difference this season? Check. Are we seeing a pattern here?

Yes they can be bold and yes they may not be as easy to wear as the plain variety, but if you get them right check trousers are one of the most stylish ways to cover your bottom half. Most importantly – and perhaps surprisingly – they’re incredibly versatile and can finish off both formal and casual dress effortlessly.

“It’s true that most men wouldn’t think twice about wearing a bold check blazer or shirt, but a pair of check trousers that are not part of a suit are still seen as a bit of a swerve,” says John Harrison, creative director at the venerable Savile Row tailors Gieves & Hawkes, whose ready-to-wear offerings include a wide range of statement leg wear, from the softly-spoken to the more declarative. “Take it too far and it tips over into costume. But if you get the balance right, it’s a really nice counter-intuitive way to re-direct the focal point of a look, which for most guys is still based on a jacket or some other piece of outerwear.”

To help would-be “check-ers” avoid being mistaken for an Ian Poulter wannabe, here’s how to wear check trousers, from the patterns to try to what to pair them with.

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How To Wear Check Trousers

Getting the balance right – as Harrison suggests – involves keeping the rest of your outfit neutral and restrained, thus letting the trousers take centre stage. “I know some guys who have the confidence to mix prints and patterns with abandon, but that’s tricky to pull off,” says Harrison. “The Pitti peacock look is a bit strong for the real world.”

“In the average office environment, I would go for a micro-check like a puppytooth or a very soft Prince of Wales, and team it with subtle, tonal variations; blazers and knitwear in black, grey and navy will set it off really nicely without looking too effortful.

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“You could even make a case for saying that, as dress codes break down and smart casual takes over the world, the ‘personality’ that used to be expressed through patterned ties or pocket squares can now be shown in a patterned trouser, especially as mixer suits – jackets and trousers that can be split and worn separately, many of which feature checks and other patterns – which are starting to prove more popular.”

Modern checks can also add flair to a dressed-down outfit. I recently bought a pair of vivid gingham-check trousers from Incotex, and by teaming them with more self-effacing pieces – a sea-blue Harrington jacket, a white polo shirt, some minimal white trainers – they stood out without descending into Caddyshack caricature.

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Similarly, a pair of houndstooth trousers will give a Mod-inflected twist to a casual weekend outfit of, say, a cashmere polo neck and black bomber jacket. “It’s quite a simple formula, really,” says Harrison. “Use the trousers to create a contrast in the outfit – check with plain, colour with muted, busy with quiet – whilst taking care not to over-egg it. It’s a way of creating interest by elevating the everyday.”

Checks To Consider

Houndstooth

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Regarded as the gateway drug of choice for check-utantes, houndstooth – and its baby brother, puppytooth – is, says John Harrison, “the perfect option for someone who wants to punch up an outfit but who can’t be too loud at work, or for someone who wants to keep it classic.”

The simple graphic pattern – made with alternating bands of four dark and four light threads – has an, ahem, chequered history; it was first seen on the Gerum Cloak, a garment uncovered in a Swedish peat bog and dated to 360-100 BC. Modern ‘toothers like Alexander McQueen and Hardy Amies give the pattern some bite.

Windowpane

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The dandy of the check family, windowpane – taking its name from its exaggerated pattern of perpendicular pinstripes, forming a square plaid – has been the choice of style-setters such as the Duke of Windsor, Clark Gable, and, latterly, Lapo Elkann. It was also Ryan Gosling’s check of choice when promoting his well-tailored turn in Crazy, Stupid Love.

“It’s easier to pull off than people think,” says Harrison. “The pattern is strong enough to offset all manner of smaller-scale patterns, so you can mix and match it with dots, stripes, and even paisleys and florals.”

Prince Of Wales

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The most nonchalant of all the checks, it was named for Edward VII, who wore it while shooting in Scotland. Although the current Prince of Wales is also a fan of the crossing pattern of irregular checks, as was Sean Connery’s Bond, Steve McQueen’s Thomas Crown, and, lest we forget, Pee Wee Herman.

“It’s more versatile than you’d think, because it comes in an array of different shades and over-checks,” says Harrison. “That makes it easy to coordinate with everything from blazers to sweaters. We always have a few Prince of Wales patterns in our collections, and they’re always big sellers.”

Key Check Trouser Looks

Formal

“In many ways, this is the hardest look to pull off,” says Harrison. “If you’re going the whole hog with a shirt and tie, and you add some check trousers, most people will think, well, where’s the jacket?”

His advice? “I’d recommend some trousers in charcoal or grey mix puppytooth or micro-gingham, and pair them with a rollneck or a soft flannel shirt and gilet, and a strong shoe, like an English brogue. If you are going to wear a blazer, tie and topcoat with them, keep them plain and neutral.”

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Smart Casual

Swapping out chinos for checks instantly lifts a smart-casual look – knitted polo and Derbys, or light, neutral knitwear and a pale blue shirt – to new heights. “This is where you can add more dandified windowpanes and modern checks,” says Harrison.

“A shearling-trimmed bomber and a chunky rollneck will also offset the checks nicely, especially with the hiking boot-type boots or chunky Derbies we’re seeing a lot of this season. It’s a look that world equally well for the modern office or the weekend.”

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Casual

This is the place where you can road-test your bolder checks – colourful Prince of Wales variations, say, or even vivid preppy checks or loud tartans, as seen on the catwalks of Versace and Dries Van Noten, among others.

“If you’re trying out a more outre check, I’d definitely dial the rest of the outfit down,” says Harrison. “A white T-shirt and Harrington-style jacket and a minimalist trainer will offset it nicely.”

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