How to holiday: a men's style guide

We say: dressed the part but young at heart – that’s the way to holiday.

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When you first see the pool and regress to a childlike state

Saturday, 9pm. The first day of holiday. 

What better way to shrug off thoughts of work emails and that two-hour flight delay than bombing straight into the pool? Of course you’ll be doing so in your new runway-worthy swim shorts (Gucci? Kenzo? Orlebar Brown? Take your pick). Last one in the pool has to make the margaritas!

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When it’s happy hour every hour

Sunday, 6pm. The hotel bar. 

Where is Club Tropicana? And are the drinks really free? While we may not be able to answer such pressing questions in this style guide, we can introduce you to the ultimate item to be seen in while sipping your sundowners: the Hawaiian shirt. From Paul Smith to Prada – this season’s styles are more colourful and captivating than your mid-afternoon mai tai.

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That smug feeling when your look’s hot, but you’re super cool

Monday, 7.30pm. Heading out to dinner.

How to dress smart when the mercury’s rising? Go for an unlined blazer or smart bomber jacket over a linen shirt – and don’t forget to ditch the flip-flops in favour of a smart pair of espadrilles or simple white sneakers. The perfect outfit to save for that blow-out holiday meal.

Holiday packing essentials

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When you don’t even know what day it is

Day unknown. The sunny spot.

Nap. Read. Sunbathe. Repeat. With holiday routines as strenuous as this, we think it’s only right to keep holiday outfit choices easy. So pick out some easy-going pairings you can mix and match: from chino shorts to casual shirts that will work well with everything.

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When the walk to your sunlounger becomes a runway

Wednesday, 11.30am. The sun terrace.

Did someone say pool party? When the chlorinated waters of the pool are shaking from the sound system and the day extends from breakfast to dancing with strangers, a simple vest and your gym towel just won’t cut it. So give your look some careful consideration with playful prints (thanks, Prada), a retro pair of sunglasses (yes, the aviator is back) and shorts as short as you dare.

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When you’re living the Gianni dream

Thursday, 2.30am. Your holiday Instagram spot…

If there’s one thing we learnt from the recent American Crime Story TV show – except that Ricky Martin is as an accomplished an actor as he is a leather-pant wearer (bravo, Ricky) – it’s that no one does fun holiday style like the house of Versace. This season the brand is celebrating its most iconic archive prints and luckily for you, we’ve got all the Medusa-emblazoned styles you need to stop onlookers in their tracks – including this exclusive T-shirt. 

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