Before you even think about what’s going into your suitcase, it’s worth considering the clothes to wear to the actual airport. After all, until they finally pull their fingers out and invent matter transporters like on Star Trek, we’re stuck with long-haul flights and all the tedium of waiting around before you even get on the plane. Now imagine your onward-journey Venn diagram – where comfort, smart luxury and practicality overlap is your sweet spot. A versatile jacket in a neutral colour sets the tone, although bear in mind you’ll want a lightweight item that you don’t mind slinging over an arm or stowing away once you’re in the air. Likewise, slip-on shoes make going through security, or extending your toes mid-flight, a breeze. A robust steel watch will keep you present in the moment, while headphones mean you can get lost in a podcast. And your trusty, comfy sweats aren’t just for WFH days. Although, since you’re on show, keep them like your mode of transportation: elevated. TOM FORD, Loro Piana and Brunello Cucinelli are the ideal travel companions.

A vacation for us typically means kicking our feet up and cramming in the calories, but we’re equally happy to dispense our style advice to get-up-and-go types. And good news, while function always takes precedence with outdoor activities, these days you’ll find techy gear you’re not entirely embarrassed to be seen in. Take French label Satisfy, which has developed high-performance pieces with clever-sounding features but that still manage to be easy on the eye. And thanks to the rise of Gorpcore, you could very easily slot DISTRICT VISION’s bright blue nylon jacket into a weekend get-up back home. Footwear is never a laughing matter for us at MR PORTER, but when it comes to hiking and other such vigorous endeavours, we recommend getting extra serious. Splash out on a pair of Salomon XT-6 rubber-mesh sneakers and you’ll save yourself any aches in the long run.

You may be playing the role of tourist, but god forbid you actually look the part (though wielding your iPhone camera every 30 seconds could give you away). Instead, think of your sightseeing outfit as nothing too far off your usual real-life wear, albeit better equipped for a full day on the move. Realistically, you’ll be racking up the steps, so sneakers are a no-brainer, although a sleek pair by Common Projects won’t get you turned away come lunchtime. You’d also be wise to keep your bits stowed away from light fingers in a compact cross-body bag, such as this one by Berluti. Elsewhere, it’s all about striking that equilibrium between elegance and ease, and pieces such as Loro Piana’s field jacket and Barena’s drawstring trousers do exactly that. Throw in a pop of colour, plus a few carefully selected summer accessories, and chances are you’ll look so good that even your glacial walking will be forgiven.

You may be thinking: I have to put more than one second of thought into what I wear to the beach? And the answer is: yes, if you want to look effortlessly stylish and not crumpled, hot and grubby. Any man can pull on an old T-shirt and even older swim trunks. But you’re a man of taste and therefore should consider playfully printed flat-front (ie, non-elasticated waist) swim shorts with a moderate inseam. Throw on a tank top (Bottega Veneta makes an elegant option) and a contrasting abstract floral-printed shirt such as this one from 11.11/eleven eleven. Layers may seem bananas in the heat, but a tank will keep you cool without requiring you to let it all hang out, and the shirt will provide some extra warmth if the wind begins to blow. Add grown-up sandals, a bucket hat and a beach-ready tote (to hold your books, SPF, towel and a beach game or two) and you’re ready for a long stretch on the sand or by the pool (we’re thinking six-to-eight hours will do it).

Even if you plan to simply do nothing while on vacation, it’s always worth packing a lightweight suit, just in case you and your companions decide to treat yourselves to a nice dinner one night. This cotton-linen suit from A Kind Of Guise is unlined, so you don’t have to worry about overheating and the tie fastening is surprisingly beautiful in its simplicity. Just remember to take the jacket and trousers out of your suitcase the moment you arrive to stave off too much wrinkling. And, since you’re on vacation, pair this look with an upgraded T-shirt, not an Oxford shirt, to keep the whole thing looking as relaxed as you’re bound to be feeling. You could, in theory, wear your sandals from the beach with this look, but why not throw a pair of loafers into the bag just in case you want to impress. Overpacked is better than underpacked in our opinion.