What To Pack For Every Type Of Holiday

In your head, you’re an international jet-setter, turning minimalist packing into an art form akin to clothing origami. In reality, you work frantically until the last minute to get everything finished, throw a random armload of stuff into a suitcase while the meter on your taxi to the airport is ticking and eventually arrive at the resort to find you’ve brought a cashmere roll neck, a cummerbund and one ski.

Or you insure against all possible scenarios by taking every garment that you own, only to give yourself a hernia lugging the bag up to the check-in desk where you’re shaken down for half your spending money and forced to put your underwear into your hand luggage in full view of your fellow passengers.

There’s a short-haul route to becoming a packing ninja, though. All that’s required is that you not only consider the kind of holiday, the climate and the activities you’ll be undertaking, but also the fact that you can cover those bases with only the barest, most multipurpose essentials. Whether you want to look cool around the pool or stylish in the sand, here’s how to take a core city break look and add to it for every beach, gym or rep-approved superclub you plan to visit.

Core Look: The City Break

Best-suited for short hops to sunny foreign cities, the constituent parts of a city break look can also be used as the base for almost any summer escape plan.

Since you’ll likely be visiting venues where chino shorts are not acceptable, it’s wise to take at least one full-length pair of khakis. Denim is relatively heavy and informal, so it’s not conducive to packing light or keeping cool, whereas versatile chinos in navy are first-class for economy. If you really want to take jeans, wear them on the plane.

Up top, not all warmth comes from the sun. Sweatshirts and hoodies are clearly casual and also thick, so take up room (unless worn in transit). A lightweight knit in cotton or merino wool is smarter and will give you more bang for your cubic inch. Similarly, a chambray shirt is a smarter alternative to a T-shirt, but can be worn open over one as an overshirt or under a knit and jacket. Layering like this is the smart way to negotiate changeable temperatures from day to day (or day to night) without exceeding the baggage allowance.

Despite many style guides describing them as ‘essential’, a suit jacket can feel a bit fuddy-duddy. Plus, whether packed or worn through check-in, it will invariably wind up more wrinkled than an unloved dish cloth, and then there’s the issue of waterproofness, or lack thereof. On the flipside, a pac-a-mac, while practical, won’t exactly go down a storm in more upmarket establishments. One space-saving alternative is to shell out for a ‘shell’ blazer in a technical fabric. Unlike wool, cotton or linen equivalents, they’re water-resistant, will happily scrunch down into a suitcase or tote and come over a little less catalogue model.

One resort wear saving grace is that there aren’t many places that you can’t go now in trainers, especially if they’re clean, white and classic. But if proper shoes are required, loafers are in the holiday spirit: they’re more laid back than lace-ups, not to mention easier to slip off in security.

Add-On 1: Beach

Even if you don’t plan on wearing much else, two is the magic number when it comes to packing swimwear: one to wear while the other airs. They don’t have to Costa packet either, but it’s worth bearing in mind that tailored swim shorts will not only look smart enough to pass as shorts away from the water, but also have proper waistbands and side adjusters to prevent you ‘hanging out’ anywhere else.

You will need to put a top on at some point, though. For maximum versatility and therefore minimal volume, T-shirts should be plain or nautically striped at a boat-push, and crew-neck, not V. Aside from being douchey, vests are effectively pointless. If you’re catching some rays, go topless; if you’re covering up, shield your shoulders.

To take stuff to and from the beach requires a bag; specifically, a canvas tote. Light and unstructured, it’ll take up minimal weight and space in the case, if you don’t use it to carry on your duty-free haul. Just make sure the straps are long enough so that it can be carried on your shoulder and not in the crook of your elbow. (Not a good look.)

Finally, to take yourself to and from the beach, you’ll also need some suitable footwear. Consider espadrilles, they’re more substantial than flip-flops so better suited for walking more than a few feet, less ‘German tourist’ than leather sandals and they keep gnarled, hairy hooves out of sight of fellow diners when out for a meal.

Add-On 2: Exercise

A holiday doesn’t always mean a rest week. After all, time and gains wait for no man. But unless partaking in a sport that requires specialist gear such as cycling, you really don’t need to pack loads of dedicated gym kit.

Your plain cotton T-shirts can double up as workout attire as well as resort wear. (Wear the one from the day before, as long as it doesn’t stink too badly.) And provided that they’re not adorned with pink flamingoes, your swim shorts can also pass as, well, shorts. Retro running styles lend themselves to this especially well, but if it makes you feel better then you can buy ‘gym to swim’ shorts that are expressly designed for this purpose.

Trainers are the sole technicality: while you don’t want to take a pair just for exercise, equally you don’t want to clump around the whole time in ugly running shoes. Flat-soled Converse All-Stars will suffice for getting a pump on, but don’t have the cushioning for a jog along the coast. Knitted trainers are the interweaving of performance, aesthetics and ventilation.

And if all your socks are secret, then it doesn’t matter whether they’re ‘sports’ or not.

Add-On 3: Lads (Lads, Lads, Lads)

This is basically just a beach holiday with added banter. But if partying, then you might want a shirt. Just not a ‘party shirt’.

Once the preserve of flight attendants, short-sleeved shirts have really taken off in recent years. For bonus fashion points, go for one with a Cuban (AKA camp or revere) collar, and a pattern that can’t be looked directly at without sunglasses. If too much of a shrinking violet to confidently rock a full-on floral, then a dark background or monochrome colour scheme can help soften their appearance.

Some trousers and sneakers wouldn’t go amiss for going out. Again, chinos will be cooler than jeans, especially in the current relaxed, cropped fit that (helpfully) will also allow air circulate. Either way, you don’t want your legs to resemble badly packed sausages being shipped to Love Island. In addition to the options previously mentioned, slip-on canvas Vans are ideal for effortlessly transitioning between beach, bar and mortally hungover breakfast.

Last, but by no means least, make sure you take plenty of protection. And we don’t mean sun.