On a map, Astypalaia has the outline of a butterfly: two broad wings of land joined by a neck so narrow that the sea is visible on both sides of the road. The island belongs to the Dodecanese, yet it sits at the group's far western edge, and its white villages, windmills and cubic houses owe more to the Cyclades than to Rhodes or Kos. For anyone deciding what to wear in Astypalaia, that position matters: this is a Cycladic island in spirit, with the wind, the light and the unhurried evenings that come with it.

Chora is the reason most people arrive. The village climbs a ridge above the harbour of Pera Gialos, a line of windmills along its crest, and at the top stands the castle built by the Venetian Querini family, its houses once forming the fortification itself. The lanes below are steep and stepped, which suggests flat leather sandals rather than anything with a heel, and the wind on the ridge can be strong even on a still day at sea level. Linen moves with that wind rather than resisting it, and a shirt worn loose over linen trousers simply lifts and settles as you walk.

For a man, the day on the ridge suits a Male Linen Shirt in White with PP Trousers 100% Linen in Sapphire Blue, both from the men's linen collection. The trousers close with walnut buttons, and the combination stays comfortable on the steepest steps. For a woman, the ladies linen set in Coral Orange does the same work on the ridge.

Below Chora, the bay of Livadi opens on a long pebble and sand beach with tamarisk trees and a cluster of tavernas behind it. It is the obvious place for a first swim, and the PP natural swim shorts in Black or Vanille belong there, in the water and on the pebbles. Further afield, the beaches of Vatses and Kaminakia on the western wing are reached by dirt road, and Kaminakia's taverna is known for its slow-cooked dishes; a day there is a beach day, and the bag should hold swim shorts, a shirt for lunch and very little else. Maltezana, on the narrow neck of the island near the small airport, has quiet coves and the remains of Roman baths with mosaic floors.

Astypalaia is also an island of long lunches. Lobster spaghetti is the local dish, served at tables close to the water, and lunch can run well into the afternoon. For these tables, the Amelia linen dress shirt in Oyster, with its walnut buttons, worn as a dress with sandals, is entirely at home; so is the ladies linen set in Light Blue. A man moving from the beach to the table changes from swim shorts into PP linen shorts in Navy Blue and a Laos Short Sleeve Linen Shirt in Oyster, and nothing more formal is expected. Oyster and Light Blue both read softly against the white of Chora, and the women's linen collection holds stronger shades for those who want them.

The evening returns everyone to Chora. Dinner on the terraces below the windmills is a little more composed than lunch, and the temperature on the ridge falls once the sun goes down. A Bliss Linen Shirt in Grey, long-sleeved, is a natural choice for a man here, worn with PP Casual Linen Trousers in Vanille. For a woman, the Amelia linen dress shirt in Dubarry carries the same tone, and the walk back down the steps is cooler than the climb.

The island is reached by ferry from Piraeus, a long crossing, or by a short flight from Athens, and it connects onward by sea to Amorgos and the rest of the Dodecanese. Of the neighbouring islands, Kos is busier and more open and Leros more private, though all three share the season. Astypalaia sits between the two archipelagos and belongs a little to both.

The season runs from late May into October. In high summer the meltemi blows across the neck of the island and the bay of Livadi can turn choppy by afternoon; the shoulder months are calmer and the village emptier, and the castle can be had almost to oneself.

Read more: What to Wear in Leros  ·  What to Wear in Amorgos  ·  What to Wear in Symi