Andros was built on shipping money rather than holiday money, and it still carries itself that way. The neoclassical houses of Chora were raised by captains and shipowning families, the town keeps a maritime museum and a museum of contemporary art founded by one of those families, and most visitors come from Athens, about two hours across the water from Rafina, for long weekends of walking and eating rather than for nightlife. What to wear in Andros has less to do with heat than with three surfaces: a mule path in the morning, a village terrace at lunch, a marble street after dark.

It is also the exception among the Cyclades. The northernmost island of the group and one of its largest, Andros has springs, plane trees, streams that can still be running in autumn and valleys terraced in dry stone. The village of Menites is known for water pouring from marble lion heads; Apoikia bottles its spring water under the Sariza name. Where its neighbours to the south are bare and wind-scoured, Andros is green in places, and in October it becomes a walker's island: the meltemi has usually eased, the days are expected to be warm rather than hot, and the waymarked network known as Andros Routes is at its most comfortable.

The paths decide the trousers. Andros Routes crosses old mule tracks, stone steps and the low, thorny scrub of the Cycladic hillside, which catches bare legs within the first kilometre. Long linen is the sensible choice: the PP Casual Linen Trousers in Sapphire Blue or Oatmeal, worn with walking shoes and a Laos Short Sleeve Linen Shirt in Mint Green or Light Blue from the men's linen collection. A walk on Andros often ends at a cove and begins again after a swim, and a linen shirt pulled on over damp skin is soon comfortable again on the path. For women, the PP linen blouse in Sky Blue does the same work with trousers of her own; on the open ridges between Chora and the eastern villages there is little shade, and its sleeves are welcome.

Chora itself asks for a little more. The town runs out along a narrow ridge into the sea, its main street paved in marble and lined with mansions, cafés and the two museums, and it ends at a square with the statue of the Unknown Sailor and a stone arch to the ruined Venetian castle of Kato Kastro. Evenings here are quiet and well dressed. A Monte-Carlo Male shirt in Vanille, with its walnut buttons, sits easily with the PP Trousers 100% Linen in Sapphire Blue; the Bliss Linen Shirt in Dark Blue has long sleeves for the cooler nights October can bring. For her, the Amelia linen dress shirt in Dubarry or Oyster, from the women's collection, belongs at a harbour dinner as a dress on its own.

Some of the island's most visited places ask for covered shoulders and knees. The monastery of Panachrantou, on the mountainside above the village of Falika, is one; village churches during a service are others. On those days the Amelia linen dress shirt stays at the hotel and the blouse comes out again, with a long skirt or loose trousers. Men need nothing more than the long trousers already worn for the path.

The sea comes at the end of the day rather than the start. Achla, on the east coast, is reached by a rough track or by boat; the smaller coves along the west coast near Batsi are easier. Swimming is done in PP natural swim shorts, in Vanille or Sapphire Blue. On land, the PP linen shorts in Beige or White carry a long lunch at a beach taverna. For anyone taking the ferry on south to Tinos and Mykonos, the wardrobe does not need to change; linen for island hopping works through why it travels so lightly.

Late in the evening the main street of Chora is almost empty. The marble has been polished by a century and a half of footsteps, a few café chairs are still out, and at the far end of it the only sound is the sea against the rocks below Kato Kastro.

Read more: What to Wear in Tinos  ·  What to Wear in Kéa  ·  What to Wear in Syros