They don’t tell you how to dress or pack in the guide books and, depending on your destination, shorts and a T-shirt won’t always cut it when you’re on holiday. Which is very much the inspiration behind today’s Style Question, where one man, headed for Greece, reached out to us for some travel advice of a sartorial nature.

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I need a cool evening outfit for an upcoming trip to Mykonos, can you help?

From @hazzcoxy, via Instagram

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The curious occasional phenomena, Politicians On Their Downtime On Holiday, perfectly underlines just how adrift some men can feel when out of their comfort zone while on their downtime. There’s no dignity in a 50-something man who spends his day in corporate suiting coyly flashing a slab of white thigh flesh because he’s found himself next to a pool in Capri. Holiday dressing for men is a fine line between looking at ease and looking appropriate; all too often the answer is shapeless polo shirts, cargo shorts and shoes better suited to a correctional facility.

But your query is a specific one, @hazzcoxy – nighttime attire that’s suitable for the bohemian party-hard idyll of Mykonos. It’s a wardrobe conundrum that applies across the length and breadth of a European summer, from drinking in the sunset at the island’s famous beach club Scorpios to drinking an Aperol spritz overlooking the rest of the Cyclades. First of all, don’t be fooled by the Instagram contingent; leave the tight, bright attire for reality TV contestants. A fresh, sleekly cut white shirt might look good with a Lark filter but it’s less so on a balmy summer night that shows up every sweat patch and crease.

Mykonos – and its counterparts across the Amalfi Coast, Côte d’Azur and Costa Smeralda – is undoubtedly glamorous, but the dress code is low-key louche rather than done up. White to match the shades of those higgledy-piggledy Aegean homesteads will offset that tan nicely but keep it breezy and softly structured; a pyjama-collar shirt from Officine Generale should do the trick. Similarly, a grandad-collar style is a great halfway point between the smartness of a shirt and the ease of a T-shirt, especially a variety in breathable, flyaway linen. There are camps that have called time on the tropical-print shirt, but if you can’t wear a pattern as the caipirinhas circulate and the waves gently lap, when can you? Just stick to more muted, less garish variants that hit the right laid-back, bohemian note.

Call me puritanical, but shorts are for the beach and pool bar only. When the sun dips, it’s time for some coverage, either loose and breezy, or cropped (a combination of both can look disconcertingly like culottes). When it comes to evening footwear, all too often men can veer towards loafers, which, on paper, sound on point, but in practise can be too hard and heavy for the tropical climes, and too slippery for those lethal cobblestone streets. Which is where the elevated espadrille steps in; it’s more formal than a sandal but much more freeing than a loafer, and a backless or pattern style will certainly add a touch of vim. And finally, don’t be romanced into adding some woven bracelets to your accessories roster just because you’ve relaxed into island life. What looks artisanal in some quaint back street looks painfully gap year at the bar; a discreet cuff should be the only trinketry you’ll need. Just add an ouzo cocktail…