There’s a fine line between getting pattern just so and going overboard – here’s how to find the sweet spot.

Animating autumn/winter wardrobe staples with the aid of a few well-chosen motifs… are we seeing a pattern here? We are, and that would usually be a striped or a checked one. Judicious deployment of plaids and bands can not only add welcome pops of colour to a season when navys, greys and blacks are the normal fallback options, it can also allow a less sober approach to cold-weather dressing, whether loosening up an overcoat or brightening up a sweater. Just remember to keep the rest of your outfit neutral – over-check is one thing, overload quite another. Lines of beauty or windowpanes of wonder? Whichever you choose, here’s a quick primer in pattern recognition.

Does the word “topcoat” conjure grainy images of mid-century businessmen trudging to their office cubicles, identikit overcoats shrouding their grey flannel suits? To paraphrase Fatboy Slim, we’ve come a long way, baby. Today’s iterations of the garment have more in common with streetwear than Mad Men-style formality, particularly when, as with this immaculately crafted checked wool Chesterfield from Casely-Hayford, it marries a traditional English aesthetic with a righteous blast of “Anarchy In The UK”-style insouciance. Wear it with a chunky rollneck and dark trousers to give the greys plenty of play, and leave the flannels to Don Draper.

Can we wear a fine-check blazer that marries suitably warm, hearth-and-home-friendly tones, and it won’t get us mistaken for an extra in Braveheart or a refugee from a particularly arduous hootenanny? Yes we clan if it’s this typically sophisticated, relaxed-yet-rigorous version from Bottega Veneta, whose navy, dark green and charcoal hues take the high-style road, and whose impeccable cut would complement negronis in Naples or scotch in Scotscalder alike. We suggest you accentuate its tailored elan with crisp trousers and smart Derby shoes, such as these from Massimo Alba and Cheaney, respectively, and you’ll be putting the “don” in Caledonian.

Nothing says “home on the range” like a classic checkered Western shirt. And this fiery, sunset-over-the-sierra number from Saint Laurent ropes all the right stylistic steers: it boasts the patented Western yoke and pockets; it’s cut from hardy, bucking-bronco-proof cotton-blend flannel; and it’s even been branded the “Nashville” shirt. Although, with its slim, alt-country cut, it’s more Mr Bonnie “Prince” Billy than Mr Garth Brooks. Stress your modern, urban cowboy cred by adding some skinny jeans, and swap the snakeskin boots for some suede Chelsea boots – from west Texas to west London. Giddy-up!

There’s nothing like a go-faster stripe to give a sporty feel, and the bold bands across the chest of this navy zip-top from Prada should leave all the downhill, cross-country, or long-distance commute competition standing. The label’s ability to overhaul the most familiar of menswear staples is in full flower here; it might be padded and hooded, but this is the sprucest, most streamlined shell jacket you’ll ever slalom or power-walk in. Add a lightweight long-sleeve T-shirt – you’ll already be thoroughly insulated – and extra snug headgear to counter those pre-dawn circuit-training chills, and those Fitbit fireworks will soon be putting on an Olympic Ceremony-worthy display.

Did you see the recent exhibition of paintings by Ms Agnes Martin at Tate Modern? Her delicate grids of pencilled lines created a kind of minimalist sensory feast, and A.P.C. – the French label known for its pared-back, but effortless cool – pulls off a similar trick here, elevating the humble stripy sweater to modern masterpiece status by knitting some graphic red strokes across a smart, semi-fitted, ribbed-trimmed navy round-neck. Enhance the art-for-art’s sake brio by teaming it with a wool peacoat and some subtly faded and whiskered jeans, and it’s a safe bet that any opinions you canvass will be more than favourable.

“Iconic” is a word that’s been thoroughly tarnished through overuse, but if it can be applied to any cotton-based casual garment, it’s surely the Breton-inspired stripy T-shirt; Mr James Dean smouldered in one, Mr Andy Warhol screenprinted in one, and Mr Jean Paul Gaultier continues to sew his haute couture creations in one. This season, Acne Studios earns its own stripes by cutting a long-sleeve version with a typically off-centre touch – an emoji-inspired motif on the chest. Put the smart into casual by teaming it with cropped trousers and box-fresh sneakers, and the only emoji you will need to concern yourself with is the “face with look of triumph” one.