There’s something reassuringly human about the inability to pack efficiently for a holiday. We’ve all been there: suitcase laid open in anticipation – while you’re busy deep-diving into the darkest corners of your wardrobe to retrieve garments you’d never dream of wearing on home turf. But as you prepare to jet off to sunnier climes, distant shores or ragged festival turf, what should you be packing to make sure you look your best? Cabin baggage allowances were sent to try even the most seasoned travellers among us. But with a little forward planning, functionality, sophistication and style needn’t go flying out of the window.

Camping isn’t what it used to be. Microlight tents and compact camping stoves mean there’s more room in that rucksack for serious festival attire. Combine playful and practical with a capsule wardrobe that screams hazy hedonistic afternoons spent milling from beer tent to sound system. (Def) Leopard-print shorts from KAPITAL guarantee the volume, with Bottega Veneta’s yellow ankle boots providing splash-proof protection from the rain. The logo T-shirt from Sorry In Advance harks back to the glory days of Woodstock, especially teamed with the rainbow chain from NYC-based Fry Powers. Sleep isn’t top of the bill at these events, so sunglasses are a must to disguise those dark circles – these sky-blue Gucci numbers do the trick nicely. Finish the ensemble with an Acne Studios crossbody bag, proportioned to fit all your party essentials. When your phone battery dies, and you’ve lost all your friends, these bold colours and upbeat prints mean you’ll still stand out in the crowd.

Why go on holiday to tune out when you can work out instead? What’s the point in lounging when time away from your desk presents a rare opportunity to smash your daily step-count record? This is a holiday wardrobe for the man who puts sport before Sangria. Breathable, sweat-wicking base layers are non-negotiable – and even better if they’re as eye-catching as lululemon’s digital-print shorts. And Wander’s activity waistcoat gives you pockets-a-plenty for protein bars and a compass (or room to stash the fruits of your foraging, depending on the terrain).

Visualise the middle ground between a youthful Mr Jack Nicholson and Mr Hunter S Thompson in his prime to decode the sartorial script on this elegant beach-bum combo. You can rely on London-based Orlebar Brown to hit the right notes on the shorts scale and teaming them with a timelessly authentic Ikat shirt from print aficionado Erdem will ensure you’re the brightest dresser on the beach. A smattering of jewellery won’t hurt either – éliou and Miansai are both a good shout to bring a touch of Beat generation panache to a summer look.

Exploring new urban pastures requires dedication and sensible footwear, so for a stress-free city break, we recommend starting your outfit from the bottom up. A sturdy suede slip-on from Yuketen should give you the breezy support you need – they’ll work either with or without socks. Knee-length chino shorts will help straddle the smart/casual conundrum without issue and the unfinished hems of these sand-coloured ones from Beams keep things feeling modern. When it comes to fending off the windchill when the sun goes down, King Kennedy Rugs has created a boxy denim jacket that looks 100 per cent holiday but feels entirely practical.

Speed boat? Private jet? A helipad landing for a two-night stay on a pint-sized Greek island where an entry is via invite only? If five-star luxury is the standard, you want clothes that are knowy rather than showy, so go for colours that are muted, contemporary and interchangeable. Subtle multi-layered detailing gives Le 17 Septembre’s short-sleeved shirt just the right amount of understated design features. Combined with Umit Benan B+’s drawstring-waist shorts and the deceptively simple vegan leather sliders from OAS, this is Scandinavian minimalism seasoned with a side order of Succession sophistication.