Jetting off to a splashy affair worthy of Mr Luca Guadagnino in the rolling Tuscan hills or the Amalfi Coast this summer? It’d be criminal to go anything other than Italian. Specifically, we recommend cutting a bella figura in Brunello Cucinelli’s soft beige linen suit that oozes laid-back elegance and will keep you breezy under the Mediterranean sun. For peak sprezzatura, skip the obvious shirt-and-tie combo and opt for the less conventional granddad collar – Mr Massimo Alba has crafted a winner in a fizzing Bellini pink that will pick up on the hues of TOM FORD’s floral silk scarf turned pocket square. Suede loafers feel fitting for the setting and Manolo Blahnik’s feature collapsible heels that’ll easily fit in your suitcase. Then finally, throw in a pair of aviators and you’ll be sure to give those stylish countrymen a good run for their euros.

If the venue of choice is a far-flung island accessible only by motorboat, you can bet on it being a more relaxed affair and leave the cravat in your closet. That said, when traditional dress is firmly ­off the menu and yet a T-shirt and swim trunks don’t feel quite appropriate, where does that leave you exactly? You’ll want to strike a balance, here – do so in almost-but-not-quite suiting in seasonally apt linen such as this cardigan by Inis Meáin and 120% Lino’s breezy slacks. Both pieces sit beautifully alongside Isabel Marant’s characteristically bohemian kaftan, which will work with your summer shorts if you decide to linger around after. As for footwear, no one will have any qualms with you getting your toes out in this instance, but Officine Creative’s suede sandals read several rungs up from a rubber flip flop. And don’t forget to layer on lots of jewellery (and your most heavyweight watch), which will elevate the down-to-earth fabrics and add to the sense of occasion.

The mores of a traditional British wedding can feel akin to a minefield for the outsider. All those rigid dress codes. All those baffling titles. All that headgear… But rest assured, unless the invitation specifically calls for morning dress – and if it does, you’ll want to book into a tailor ahead of time – no one will have anything but compliments to lavish on you if you show up in an impeccably cut Canali suit. Not much of a tie guy? Pack one just to be on safe side. You can always whip it off for the reception, although we’re confident this silk one by Etro will stay firmly on your person. Likewise, if you’re already dreading having to part with your sneakers, then these chocolate brown suede Derby shoes by our very own Mr P. provide a touch of smartness albeit with the comfort you’re accustomed to. Trust us when we say an umbrella will figure into your outfit on the day, planned or otherwise, so might as well come equipped with the most elegant pick you can find. This one by Francesco Maglia is a conversation-starter on its own accord and nods nicely to the Anderson & Sheppard pocket square.

Among the trickier destinations to dress for is the vibrant – and sweltering – metropolis. Think the riotously colourful do in Mumbai that stretches out across three-to-five business days. Think a cross-cultural affair at a riad in Marrakech or villa in Mexico City where you’ll be feasting into the early hours. Our advice? Ditch the trussed-up tailoring and embrace the ambiance with plenty of colour, pattern and texture. Not an awkward clash-fest, though: the floral print of Acne Studio’s fil-coupé shirt alongside Dries Van Noten’s dusty pink linen blazer is exactly how to do it right. Here, we’ve juxtaposed those softer hues with a deep-orange cropped trouser by Nanushka, which transitions nicely into the earthiness of Manolo Blahnik’s raffia Capuleti mule (we’re calling it the shoe of the summer). Finally, Bottega Veneta’s intrecciato bag in an indigo denim might be an unorthodox pick for someone’s nuptials, but in our view it adds an unexpected, offbeat notes that turns a good outfit into a great one.

How to nail the well-to-do West Egg aesthetic in a way that feels contemporary and, dare we say, cool? It’s not a mission impossible, we assure you. The secret is simply to inject splashes of personality in the finer details and poke a little fun with contrasts. Start off with that Ivy essential of a navy blazer – this double-breasted number by AMI PARIS will do you nicely – and layer it over Nili Lotan’s more relaxed spin on the stripy blue Oxford shirt. But then, rather than your bog-standard suit trouser, opt for these capacious white cargos by the always-elegant UMIT BENAN B+ for a touch of lightness. The accessories will play a crucial role in knocking it all down a peg, too – trading the tie for a vibrant bandana scarf will add a street-smart-meets-old-world flourish. Meanwhile, Gucci’s retro black-and-white horsebit loafers read quirkier than classic tan. To finish, play off your Reverso (so Hamptons) with edgier hardware by the likes of Tom Wood and Lanvin – all the better to keep the chattering classes on their toes.