It’s hip to be square – here are six ways to get the check this season.

“You better check yo’ self before you wreck yo’ self,” advised rapper Ice Cube back in 1992. Scholars have spent the intervening decades trying to divine just what he meant, but we think we’ve finally figured it: he’s advising his style-savvy listeners to embrace the myriad possibilities of the grid-based patterns – tartans, windowpanes, houndstooths – that are a colour-boosting mainstay of menswear collections. But, in doing so, to avoid crossing that line – or, in this case, multiple lines – where clashing motifs drown each other out. Scroll down to discover six ways to square up.

The best way to open your checking account? With a bold statement that will generate plenty of interest. That’s exactly what this gentleman has done, with a jacket whose quilting softens the punch of its vivid check, while still being pretty heavyweight on the autumnal swagger. The cartoon T-shirt makes a nice point of contrast – any more squares and he’d resemble a human ludo board – and he wisely opts for some toned-down jeans to offset all the above-the-waist action. Throw in the kind of attitude that says “My water isn’t carbonated, but I’m still badass,” and you’ve got a look that’s totally, well, money.

Checks don’t have to shout from the rooftops; you can sneak them into a cooler, more sober outfit. Case in point: the gentleman pictured here, who clearly knows a thing or two about killer combinations. Here, the grey, black and tan tones of the check button-down riff on the muted palette of the blazer, waistcoat and chinos. He’s also putting the whole smart-casual thing through the wringer by leaving the tie loosened, the shirt untucked, and the shearling gloves fingerless, making him equally primed to nod sagely on whichever front row he’s heading for, and to bust his best Shiggy moves at the after-party.

Oversized. If that word summons daunting visions of, say, puffer jackets with the dimensions of bouncy castles, or “pumped” sneakers that resemble hovercrafts on steroids, rest assured that there’s a way to sample this trend that only requires a draped, unbuttoned XXL shirt in a graphic check. This gentleman shows us how it’s done, his voluminous shirt boasting a pattern that’s eye-catching without being eye-popping, the better to frame the studied calm of the T-shirt and jeans. The soft collar, the drooping pockets, and the ostentatiously rolled sleeves are further proof that oversized certainly needn’t mean over-egged.

Certain checks can conjure up the rugged frontier vibe of the Old West, even if the only steer you’re ever likely to rope is a ribeye served with truffle and black pepper butter at your local Gaucho. This gentleman channels a haute version of Mr Clint Eastwood’s Man With No Name in a rough wool jacket of dust-bowl buff, grey and blue checks which, with its exposed seams and chunky cuffs, would serve equally well as a rugged style statement (particularly when paired with layers of impeccably neutral beige, as here), or a campfire blanket to accompany a hearty alfresco bean supper. Not bad, not ugly – just good.

There’s a reason that tartan has endured since the third or fourth century AD, and it’s not just so that the clan MacDougall and the clan MacDonald can tell each other apart, or that Mr Lewis Hamilton can don a kilt as a mea culpa after skirt-shaming his nephew; it remains contemporary because it lends a bold pop of warp-and-weft colour to an outfit, whether you’re adding some Black Watch trousers to an evening suit, channelling Mr Jon Pertwee’s Time Lord turn in Doctor Who in a generously-plaided scarf, or, as per this gentleman, tucking a sharp scarlet tartan shirt into a pair of high-waisted jeans for a 1980s retro look that recalls Haircut 100, whose debut hit, now that we think of it, was called “Favourite Shirts”.

In the spirit of fashion’s most cherishable hybrid words – “shacket”, say, or “jeggings”, or, Lord help us, “skorts” – we bring you the camcheck. This gentleman proves that checks don’t have to be rigidly geometric to make the grid, sorry, grade; recent collections from the likes of Lanvin, Gucci and Dries Van Noten have come at them from a different, more playful angle, whether disrupting their lines, or patchworking different proportions and patterns to create something decidedly non-Euclidean. Here, the bleached camo pattern “bleeds” into the check, the pockets are at cross-purposes, and the gentleman carries it all off with a dialled-down T-shirt, a knowing smile and, just in shot, a moustache that’s just the right side of ironic.

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