“We’re all going on a summer holiday,” declared Sir Cliff Richard in his 1963 hit with The Shadows, “Summer Holiday”. Two decades later, Madonna informed us that if we took a holiday, “it would be so nice”. A further 36 years on and we’re still wistfully picturing ourselves on a sandy beach, the warm breeze in our hair, the sea lapping at our bare feet and possibly a fruity cocktail in our hand. Only we’re no closer to solving a knotty conundrum, and one for which neither Sir Cliff nor Ms Ciccone provided any insight. Namely, what to pack for said time to celebrate. One MR PORTER reader is going away for 10 days and, rather than turning to a pop star for guidance, we asked Mr Stephen Doig, men’s style editor at The Daily Telegraph, which items of clothing should make the cut. Now, when it comes to where to spend your annual leave, we hear there’s fun and sunshine, enough for everyone, at Club Tropicana (also the drinks are free).

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How many outfits should I pack for a 10-day holiday?

From @georgecollison, via Instagram

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Despite a job title that might assume a degree of authority on all things sartorial, the ability to pack appropriately eluded me for an extraordinary length of time – cashmere sweaters were left untouched in Amalfi coast heat, the optimistic addition of shorts in rain-slicked Stockholm and the unfortunate timing of a polar vortex in the Catskill Mountains that didn’t quite go with the “rustic denim woodworker” attire I’d brought along. Suitcases bulged with the great and the good, only half of which was ever worn, or appropriate. It was only the help of an organisational Ms Marie Kondo-style guru (for a feature I was enlisted to write) that précised my haphazard packing.

Assuming your summer sojourn is in warmer climes (not always a given – I write this from a drizzly Icelandic fjord), there are four situations you’re likely to find yourself in. Let’s assume you’re going to be swimming, exploring, indulging and sampling a few sundowners. You need a) beach/poolside attire, b) easy daytime attire, c) smarter ensembles for certain outings and, if your itinerary includes it, d) a nod to formalwear.

Let’s start with the lounger situation. Take a couple of pairs of trunks (opt for the budgie-smuggler variety only if you share a gene pool with Mr David Gandy and are posturing off Capri) in a subtle print that will easily work with a neutral set of T-shirts – a stack of white, black and navy shades is a no brainer – alongside slides. Add a pair of sandals, should the poolside bar beckon, and that’s that baseline taken care of.

Next up is your daytime set-up, whether you’re dutifully ticking off the tourist sights or pottering through Positano alleyways. Let’s work from the head downwards. Invest in a straw hat – the bucket variety is relegated to festivals only – in either a panama or fedora style. Then it’s sunglasses (sleek black and tortoiseshell can be alternated depending on the outfit) and a shirt. Lightweight, linen and collarless will mark a departure from the more structured variety that most men wear during the week and a seersucker fabric will be breathable. Depending on temperatures, it’s wise to pack a couple of pairs of chinos interspersed with shorts. A selection in beige, navy, white and something more vibrant, such as contrasting stripes, will work for every eventuality. Then consider your daytime shoes: boat shoes, driving shoes and leather sandals that cover the toes (do you want them making an appearance during a white-tablecloth lunch?). A lightweight cross-body bag will house everything neatly, will pack easily and won’t look as mumsy as a canvas beach bag.

Night-time activities divide into two camps: the cocktails-at-dusk-overlooking-Portofino scenario and the siren call of the Balearic beats (and how swiftly the former can descend into the latter after an Aperol or five). For your smarter sundowners and more formal dinners, the chinos and shirts can remain intact, but switch up the final touches. A blazer in a half-canvas means the back section is unlined for extra breathability, and while the idea of a seersucker jacket brings to mind twee Colonel Sanders candy stripes, varieties in black or white look sleek and minimal. Add driving shoes or the new smarter take on the espadrille, the dresspadrille. And, for a little more oomph, pack a couple of brightly printed, camp-collar shirts to watch that sun rise over Formentera.

Then we move into more upright territory, which is obviously entirely dependent on the situation you find yourself in, but a continental wedding or sumptuous cocktail party in some Florentine palazzo requires turning it up a notch, but not to a degree that’s uncomfortable. So, keep your blazer, but switch up for a smarter pair of trousers, and instead of a tie, there’s always the option of a lightweight silk foulard, a nod to formality, but with a dash of sprezzatura. A silk shirt can also act as your friend here. It’s light and airy, but adds a sheen of after dark, particularly with some discreet evening slippers.

Throw in a cashmere sweater for when the temperature drops, a hefty amount of bug spray and a couple of well-intentioned Man Bookers alongside the smuggled Jack Reachers and you’ll be the most stylistically informed as you head for the departure lounge.