5 Outfits Every Man Should Pack for a Winter Sun Holiday

Words by Tony Wilkes


For many residents of the northern hemisphere, winter brings dark, cold and often wet weather. While there are ways to deal with the seasonal blues – staying active and eating healthily helps no end, as does throwing an all-out party – an alternative route is to up sticks and seek balmier climes. But what to pack? Whether you’re the kind of person who wants to explore or simply plans to stretch out by the pool, here’s your guide to the outfits you’ll need for your much-deserved getaway.

Seeing the Sights

You chose your destination with the greatest care; you know exactly what there is to see, and you planned it all in a detailed itinerary. For staunch explorers, we’d recommend some holiday heavy-lifters: a lightweight field jacket and cargo trousers or shorts. These pieces come equipped with plenty of pockets, though it’s still best to carry a hold-all or cross-body bag if souvenir hunting is the aim. Practical sophistication can be achieved through similar neutral tones – lighter shades are best for the heat – alongside a pair of refined yet comfortable trainers, primed for racking up the steps.

By the Pool

Can a winter-sun holiday be truly such without winding down by the pool? You won’t go wrong with swim shorts from Ché, Frescobol Carioca and Vilebrequin – the latter’s signature Moorea pair requires no less than 32 steps to construct. Complete the look with a classic bowling shirt and a selection of trending men’s jewellery. Tom Wood and Le Gramme offer minimalist styles everyone can pull off, as does The Ouze – a new brand arrival – which hand-makes each piece in its Brighton studio.

In the Town

Perhaps you’ve found, in a place tucked away, the best spot for lunch or a coffee. On these laid-back outings, this is your chance to have fun with print. The safest bet – paradoxically – is to go all in with a matching set. This way you’ll avoid any potential clashes. When working with one printed piece, it’s best to balance it with something plain in a colour that’s similar. Commas, Ché and Casablanca offer some of our favourite no-brainer combos – and make getting dressed a breeze.

Out to Dinner

Packing a lightweight suit is among the best decisions you’ll make before your winter-sun getaway – essential fare for any impromptu restaurant discoveries. Team a relaxed blazer and trousers, preferably linen, with a classic polo to keep things refined but relaxed. Corneliani, Canali and Pal Zileri offer some of the best summer options. Based in Italy, these world-class tailors deliver suits that are soft, unstructured and easy to wear – and can be expertly fitted to you. Simply book an appointment with a made-to-measure expert in-store.

At the Party

Whether you’re dressing for a night out at home or abroad, the same advice applies: get out that head-turning shirt. This may mean a print (look to the likes of Jacquemus, Casablanca and Amiri), or ornate embellishment. When it comes to your lower half, opt for trousers of sophisticated simplicity underpinned by an equally restrained pair of loafers or sandals. You want your outfit to be loud – not deafening.

Holidays

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