Packing for the Cyclades or Cornwall? How to dress for every holiday mood

Telegraph

21-07-2025

It's that time of year when everyone is giddy with excitement for summer holidays. For some of us, part of the anticipation is planning what to wear. It doesn't matter how many cotton voile kaftans or linen shirts you own, it's almost impossible to resist scouring early summer sales for new swimsuits, sundresses and sandals – a kind of retail 'holiday goggles', if you will.
Perhaps we do it because different holidays call for different aesthetics. Take my upcoming stay with relatives in the south of France: for weeks, I've been trawling Vinted for exactly the right kind of dress for strolling around Provençal villages – my efforts were rewarded when I stumbled across a white cotton Dôen number with just the right degree of 'milkmaid' appeal.
If Cornwall or Devon is more your speed, a degree of meteorological prep for all eventualities is required. Chunky cotton knits are ideal for throwing over shorts and swimsuits if temperatures drop, along with a waterproof in case the heavens decide to open. Beyond the practicalities, a subtle nod to nautical style also feels appropriate.
A Spanish holiday might call for a more bohemian feel, with embroidered blouses and handmade espadrilles, while a Greek island escape suits a wardrobe that shares the same unfussy, minimal appeal as a port-side taverna at sundown.
It's a literal take on holiday dressing – a bit like wearing florals to the Chelsea Flower Show or crisp whites to Wimbledon – but it's also part of getting into the spirit of wherever you're going. Eating your bodyweight in gelato in Italy or having a pastel de nata at every opportunity in Portugal isn't something you can't do elsewhere – it's just more fun in the right context.
Of course, curating your holiday wardrobe is only half the challenge. Fitting it all into a Ryanair-approved carry-on is quite another. Succeed, and you've won the holiday season before you've even set off.
French girl summer
This look takes its aesthetic cues from Brigitte Bardot and Jane Birkin in the 1960s. Tie a scarf around your hair, toss your belongings into a wicker basket and, very quickly, you'll start to resemble the sort of person who knows their mer from their mère.
Nobody understands this better than Morgane Sezalory, founder of Sézane, who likes to escape to Cap Ferrat with her family. 'I always gravitate towards simplicity – timeless, essential pieces that I can mix and match throughout the season. A crisp white shirt or a well-cut pair of shorts are staples for me,' she says.
Accessories help these wardrobe staples transition into evening: 'A beautiful pearl necklace like the Morgane or a statement belt like the Selena can completely transform an outfit from day to night, especially when worn with a pair of heeled sandals,' she adds.
Greek island goddess
Silk Astrea dress, £350, Hansine
Pared-back and effortless should be the watchwords when it comes to dressing for the Greek islands – the sartorial equivalent of crystal-clear water lapping at a pebbled beach. Think sun-bleached linen, traditional leather sandals, or one of Hansine's billowy silk dresses, loved by Kate Moss and Sadie Frost.
The label's founder, Hansine Johnston, was born in Greece and created her collection with island summers in mind. They make for wonderfully lightweight packing: 'I always say that when you're in the Greek sunshine and light, you see colour in a completely different way,' she says. 'I pack five or six Rhodes dresses, some in neutrals and darks, and others in super-light colours. As the dresses fold up so small, I can honestly fit almost two weeks' worth of looks into one hand-luggage suitcase – with a bit of room left to bring back treats. Since I often visit the Cyclades islands, which are really windy, I love how our fabrics and prints on the silk cover-ups move in the breeze.'
'Dolce vita' dressing
Gingerbread cotton-blend midi dress, £790, La Double J x MyTheresa
In Italy, maximalism is the order of the day – at least, if you ask JJ Martin, the American-born, Milan-based founder of La DoubleJ. Martin's collection is a celebration of colour and print that truly comes into its own in the land of pizza, pasta and la dolce vita.
Different parts of the country call for different moods, though. 'I just spent a weekend in Como where we had lots of very chic meals with Comasco families – very classic Italian – and there I was wearing a classic printed shirtdress, but very tidy and neat,' she says. 'When I'm spending my weekends in Forte dei Marmi I'm on the beach most of the time. The Salt'n'Vinegar knit set is super chic and easy – the perfect beach day look.'
Martin is something of a master when it comes to the myriad ways to dress for the heat: 'I'm heading to Stromboli in August where it's going to be blazing hot. There, I'll be bringing a lot of cotton pieces – we'll essentially be sitting on a volcano, after all... At my ten-day Vipassana retreat in Tuscany, it'll be hotter than Hades so I'll just be living in the new Meditation tee in terrycloth.'
Nautical by nature
When it comes to a British holiday, you have to be prepared for all eventualities, advises Pip Durell, the former Vogue stylist and founder of women's shirting brand With Nothing Underneath. Durell grew up in Devon and returns as often as she can. 'The unpredictability of the weather is actually what I love,' she says. 'Taking a brisk dip is obviously preferable in golden sunshine, but an unexpected downpour? Well, that just justifies a fish and chips lunch – the Winking Prawn in Salcombe is my choice of shelter.'
Naturally, her wardrobe is dominated by her own designs, chosen for their practicality. Shirt and shorts sets, along with a cotton knit for tying around the waist, just in case. '[Seersucker] is perfect for the heat, and in a pre-crinkled material that can be pulled out of a case and worn straight away, no ironing required. The other set I always reach for is our hemp... in a slightly weightier material that gets softer with every wear. Hemp is thermodynamic, which means it keeps you cool when it's hot and warm when it's cold – ideal by the coast. I like to mix up my blues and pair them with Birkenstocks. That's my summer uniform.'
Spanish señorita
For some, summer isn't complete without a visit to Spain – whether it's the blustery Atlantic coastline of the north, the bohemian party vibes of Ibiza, or the sandy beaches of the ever-popular south. 'It's a season of joy and vibrant energy, and I like to reflect that in my clothes,' says Montserrat Álvarez, founder of accessories brand Heimat Atlantica. 'Galicia – where my roots are – is always part of my summer. I love the northern coast in summer, especially the small islands scattered across the Rías Baixas. There's something magical about their wild beaches and quiet charm.'
For her, a holiday wardrobe includes quintessentially Spanish staples, like rope-soled shoes. 'A crisp white cotton dress, flat espadrilles and silk cotton bandanas for the head are my go-to. And I like to add playful touches with one of our handmade bags.' There's always an element that reminds her of happy holidays past, too: 'A unique souvenir that no one else has, and that instantly transports you back to a special moment.'