When it comes to summer holidays, we all know the importance of planning ahead. Hotels get fully booked. Flights skyrocket in price. Nobody wants to be left frantically searching for last-minute deals at the busiest time of the year, which is why we tend to have our affairs in order weeks, if not months, in advance. If only we showed the same foresight when it came to the contents of our suitcases.

Instead, the days and hours leading up to our departure tend to be marked by a creeping sense of dread as we realise that, despite having planned our trip down to the very last detail, we haven’t given the slightest thought to what we’re going to wear. Little wonder that so many men who manage to look presentable in their day-to-day lives seem to lose the plot, sartorially speaking, a soon as they set foot on foreign soil.

Gentlemen, it doesn’t have to be this way. With just a little forward planning and a few tactical purchases, we can all make life so much easier for ourselves. And, after all, isn’t that what going on holiday is all about? That’s why, for this edition of MR PORTER’s Dress Code, we’ve put together five outfits suitable for five different trips.

However you enjoy spending your summer, whether it’s exploring new cities, enjoying the great outdoors or just soaking up the sun, piña colada in hand, there’s no excuse for not doing it in style.

There comes a time in a man’s life – and if he’s a misanthrope, it can arrive quite early – when he no longer wants to waste his precious downtime on crowded beaches or queuing up to look at the ceilings of old churches, and would much rather spend it in a state of blissful relaxation far away from anywhere and anyone. When this happens, his focus shifts from city breaks and beach holidays to “retreats”, where the goal is to retreat and, through retreating, find some temporary sense of inner peace. These can take the form of anything from yoga and wellness breaks to digital detoxes. If you’re into doing things yourself, it might just involve disappearing to a Tuscan villa or Moroccan riad for a couple of weeks.

In instances such as this, you might think that what a man chooses to wear is largely irrelevant, and of course you’d be right. We go on holiday to escape the pressures of our daily lives, and this includes the pressure to conform to a dress code. For that reason, this look has been put together with a luxurious level of comfort in mind, and is to be taken as nothing more than a mere suggestion.

If luxurious comfort is the goal, there are few better places to start than with a diaphanous silk shirt from Saint Laurent. This one, cut with a mandarin collar – note how it doesn’t quite meet in the middle, distinguishing it from the almost identical grandad collar – bears a print inspired by the traditional textiles of Marrakech, a city that the brand’s founder Mr Yves Saint Laurent would often retreat to when it all got too much. It’s worn here over a soft jersey tee with cotton drawstring trousers and a pair of sandals from Dries Van Noten.

The first thing to determine before embarking on a sailing holiday is exactly what kind of sailing holiday it is, as this will go a long way to deciding your mode of attire. Ask yourself: are you planning on doing any actual sailing? If so, you might want to invest in some proper technical gear (we can recommend Musto Sailing). If not, and you see sailing as more of a leisurely pursuit, in which you spend the day bobbing around on a luxury yacht somewhere off the coast of the Italian Riviera before docking at nightfall and heading to dinner at a nice restaurant, then read on.

The nautical-but-nice look so beloved of mid-century style icons such as President John F Kennedy is something that works as well on land as it does at sea, and is grounded by a good pair of deck shoes. We’re partial to these, designed by the irreproachably Gallic Arpenteur and made in collaboration with cordwainers Paraboot. A polo shirt is the next item to check off the list. There are few garments a man can own that are as timeless, versatile and just plain stylish as a white polo, and this waffle-knit cotton version from Ermenegildo Zegna is a particularly refined example.

Add a pair of neatly tailored trousers in navy blue, the perfect foil to a white shirt, and all that’s left to do is to finish off the look with a light dusting of Breton stripes. We suggest using this as an accent, rather than the primary element of your outfit. Try draping a striped sweater over your shoulders or carrying a striped tote. None of this is any good at keeping you dry, of course, but given that you’re not going to be manning the mainsail any time soon, that shouldn’t be too much of a problem.

The rules of dressing that govern our daily lives go out of the window on the beach, a place where, during summer, it’s perfectly acceptable to appear in public dressed in clothes that are no less revealing than underwear. This minimalist approach to dressing shouldn’t imply a lowering of one’s standards, though. There’s still plenty of scope to be well-dressed within the context of an outfit as simple as a pair of swim shorts and a shirt.

Let’s begin with the former. If you’re heading to the beach, swim shorts should be the very first thing to book a place in your suitcase. If in doubt, avoid anything too skimpy – unless you feel entirely confident, it’s best to err on the side of modesty – and steer clear of achingly unfashionable knee-length board shorts. Aim for a pair that finishes around the mid-thigh, such as these seersucker shorts from Thom Browne. Pinks and whites flatter olive skin tones, so if you’ve got pale skin it’s worth investing in a darker pair. If you tan well, consider taking two pairs so that you’ve got something else to wear once your legs have had a chance to take on a bit of colour.

What else? You’ll probably want a short-sleeved shirt to throw on before making the short lunchtime stroll from sunlounger to beachside bar. Opt for one with a camp collar and a subtle floral print, with particular emphasis on the word “subtle”. The toned-down patterns of this shirt, from the British casualwear brand Albam, keep it from straying too far into Elvis In Hawaii territory. Finishing off the look we have a pair of Mexican huarache-style sandals from Malibu, an eco-friendly footwear brand based in – you guessed it – Malibu. And, don’t forget the essentials: a towel, some SPF, a bat-and-ball set, a pair of sunglasses and a sturdy beach tote to carry it all in.

And so to the eternal dilemma of the man abroad: how to avoid looking like a tourist. Granted, it’s not easy when you’ve got a camera around your neck, which is why we’ve eschewed the hefty zoom lens in favour of something a little more discreet. This Leica Sofort works with instant film, making it perfect for capturing those spontaneous moments that make a holiday. But, look. We’re not here to tell you how to take photographs, and besides, when it comes to avoiding the dreaded “tourist look”, your choice of camera is nothing compared to your choice of clothes.

There is a tendency among certain men, especially those travelling from boreal areas to warmer climes, to dress for a city break in clothes that would be better suited for a four-day jungle trek. We’re talking hiking shoes, wide-brimmed hats with chin straps, ripstop shirts and combat trousers – the sort of thing that you might find at specialist outdoor stores. There’s a time and a place for this, but it’s not in the city. There’s nothing more incongruous than the sight of a man strolling the paved streets of, say, Cartagena, dressed as if he were planning to spend the afternoon paddling up the Mekong Delta. At best, it looks a bit silly; at worst, it implies that he expected to arrive in a city without basic infrastructure.

A simple rule to follow, then: in cosmopolitan cities, wear cosmopolitan clothes. With that in mind we’ve thrown together a versatile, layered look that’s perfect for cooler cities, such as Amsterdam, but that can be easily adapted for warmer ones, too. Just lose a couple of the layers and switch the Mr P. trousers for a pair of shorts.

Mountains or sea? A beach break might be the default choice for most summer holidays, but there’s just as much sun and a lot more fun to be had by heading for the hills. If there’s one downside, though, it’s that you’ll need to put a little more thought into the contents of your suitcase. This is doubly true if you have any interest in looking good. Aesthetics shouldn’t really be your primary concern when shopping for outdoor gear, of course – there are far more important things to consider, such as whether what you’re buying keeps you warm and dry. Outdoor brands know this and, as a result, many of them prioritise function over form. Others, such as Arc’teryx, And Wander and Patagonia, realise that it’s possible to do both. Commit their names to memory and you’re more than halfway there.

Embrace colour. Dressing for the great outdoors is one of the only occasions in your adult life that wearing primary colours is actively encouraged. An outfit incorporating large swathes of red, green and yellow might draw strange looks in town, but as soon as you’re on a hiking trail that’s just good visibility. Context is everything. Now, give some proper consideration to what to wear on your feet. As with the rest of your outfit, it shouldn’t be necessary to compromise looks over utility. Yes, hiking boots and sneakers used to be the ultimate anti-fashion statement, but that was before brands such as Prada began to include them in their outdoors-themed runway collections. And while Prada effectively created the market for smart-looking hiking boots, it didn’t fill it – you’d be mad to take a pair of them on an actual hike. That fell to brands such as ROA, whose hardwearing boots and sneakers are the perfect marriage of function and form.

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