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 on the beach, here’s your guide to the outfits you’ll need for your much-deserved getaway.

For the Day Out

Are you an avid planner or happy to see where a holiday takes you? Whatever the day’s schedule, a man needs outfits that balance comfort with laid-back style. The best bet? A classic button-down worn with neutral trousers or shorts and a roomy bag for the essentials. You can also layer with a T-shirt or a lightweight knit if temperatures drop – a helpful tip for the evenings. On your feet, we’d recommend a pair of trending boat shoes or comfortable sneakers. You’ll want to choose the latter if you’re walking long distances.

For Taking a Dip

What defines first-class swim shorts? Beyond comfortable fits and quick-drying fabrics, today’s best pairs are so well cut they work just as well outside the water, too. Whether you prefer cool and simple or tropical prints, you’ll find the most elevated styles from Ché, Frescobol Carioca and Vilebrequin – the latter’s signature Moorea swim shorts demand 32 steps, many of which are executed by hand.

For the Beach Party

As we wrote in our latest guide to men’s partywear, TOM FORD has long cemented its status as the ultimate in black-tie dressing – but what about for the beach? The brand’s supple shirts, cut from fine cotton and silk, work seamlessly with its tailored shorts for a sleek yet effortless look. Alternatively, you won’t go wrong with a party shirt from Casablanca, Jacquemus or Amiri. Just don’t forget the finishing touches: a pair of the best collectable sunglasses, plus understated jewellery from Tom Wood, Tateossian and The Ouze.

Trending: Print

The easiest way to introduce print? Follow a formula. If you split your outfit in two, choose a motif for either north or south, letting the other remain neutral for balance. A bright shirt is the obvious choice – look to options from Valentino, Dries Van Noten and Dolce&Gabbana. But the easiest option? Go all in with a set. Like the matching components of a suit, these outfits – from the likes of Commas and Amiri – guarantee impact and always look put together.

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