Sometimes all it takes is one left-of-field collection or one particularly inventive streetstyler to challenge all our preconceptions about an item of clothing. In the case of the rugby shirt, it’s Story Mfg.’s coveted stamp of approval that instantly gave us pause. Here, the Brighton label has reworked the rugby in an oversized silhouette and not-your-PE-kit pink. Is it the easiest piece to pull off? No, not really – but when have we ever shied away from a challenge?

Here we’ve teamed ours with sneakers and sweats, which could easily land you in loungewear territory, but ASICS and DRKSHDW by Rick Owens provide just enough edge for it to feel deliberate. In the same vein, a gilet over a rugby shirt might read a little investment-bank-away-day on paper, but we dare you to find a finance guy with stash that’s as perky and characterful as this piece by ARKET. That said, we still advise offsetting it all with some hardware just to make it abundantly clear you won’t participating in any contact sports (or FX trades) – we’re fans of Tom Wood’s chunky silver rings and a Maple necklace. And if you really want to reaffirm that you’re a man with fashion nous, there’s nothing like a little Nicholas Daley to do so.

The rugby shirt is a shapeshifter nowadays, as at home in the coolest bars in Shibuya as it the quaint pubs of Surrey. That said, there’s something about the rugby in its natural habitat of rolling green fields that works especially well. In more rural setting, we’d tend towards unflashy, laid-back hues and minimal variations on a theme (best not to stick out as a townie). This striped shirt by Adish is a brilliant pick, and will sit perfectly alongside wholesome, practical footwear such as Officine Creative’s desert boots.

But wholesome and practical needn’t be antithetical to considered (not in our world anyways). Plus, who knows who’ll you’ll come across on your Sunday ambles? Throw on a hardy workwear jacket – you can’t go wrong with La Paz. Then pack all your bits into an earthy tote bag such as this tasselled number by Adish. And let’s talk about these ridiculously versatile Monitaly Riding pants – they’re spun from seasonally appropriate linen, cut for a roomy fit and, if you’re clever enough to keep them mud-free, totally appropriate for work the next morning. All you’ll need from there is a smart pair of shades and a touch of silver and you’ll be the most stylish walker for miles.

Call it the Drake’s effect – that knack for recasting heritage, boarding-school silhouettes as polished, contemporary and, crucially, cool. They did it with the tie – right now the most subversive piece of kit you could have in your arsenal – and they’ve done so again with the rugby shirt, cooking up this creation in a delicious blend of merino wool, cashmere and silk. Laid-back yet undeniably elegant, it’s a garment worth adding to your office-day rotation if yours isn’t the sort to do suits. The secret, here, is to complement it with pieces that will keep things elevated – lest a client-facing presentation pop up unexpectedly.

A crisp mac goes a long way in smartening you up, and you could do far worse than to turn to the folks that invented it. Sprinkle in a bit of The Row – banana canvas tote here, black jeans there – which will automatically fast-track you to looking like a million bucks. Why not throw on a baseball cap, too, just to keep everyone on their toes? It’s a piece that can prove tricky in work settings (the men of MR PORTER ostensibly approve), but, post-Succession, no one will have anything but nice words to say about this one by Brunello Cucinelli. Finally, ground it all with some VINNY’s suede loafers, which come equipped with sturdy, commutable soles.