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.

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.

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.