Few islands in the Cyclades make the case for packing light as plainly as Sikinos. It lies between Ios and Folegandros, with a few hundred permanent residents, one small port at Alopronia and a Chora strung along the ridge above it, and a list of what to wear in Sikinos could be written on the back of a ferry ticket. The island is walked more than it is driven. The garments that serve it are the ones that can climb a stone path at noon and sit at a taverna table an hour later without needing to be changed.

Arrival sets the pattern. A road climbs from Alopronia to Chora in a long series of bends, and the local bus is timed, loosely, to meet the boats; the alternative is the old stepped mule path, slower and with the better view. Either way the day begins with a climb, and the port and the ridge feel like two different climates: the harbour sheltered and still, Chora open to whatever wind is crossing from the north.

Chora is really two villages. Kastro, the older quarter, was built as a closed ring of houses whose outer walls formed its defence, with a small square and the church of Pantanassa at the centre. Chorio spreads up the slope beside it. Above both, the fortified monastery of Zoodochos Pigi stands on a crag reached by a long flight of steps, and from its terrace the view runs across open water to Folegandros on one side and Ios on the other. The steps are steep, the stone holds the heat by midday, and the monastery, like the island's churches, is a place where covered shoulders are expected and a hem below the knee is the respectful choice.

For him, the day starts in short sleeves. A Laos Short Sleeve Linen Shirt in Light Blue, worn loose over PP linen shorts in Beige, sits well against whitewash and does not cling on the climb, and enough colour to avoid the uniform look of a fortnight in white is easy to find in the men's linen collection. For the walk to Episkopi, on the western side of the island, where a church was built into a Roman-era funerary monument, long trousers make more sense than shorts. The path is lined with thyme and low, thorny scrub, and the PP Trousers 100% Linen in White keep the legs covered while letting the air through.

For her, the Amelia linen dress shirt in Dubarry belongs to Alopronia, where lunch is taken a few steps from the water and a single dress is all the afternoon asks. It is cut to the thigh, so it stays down at the port. For the monastery and the churches of Kastro, the PP linen blouse in Sky Blue, worn with loose trousers that cover the knee, meets the custom without looking like a concession, and a ladies linen set in Mint Green covers the days spent between beach and village.

The swimming is at Alopronia itself, at Dialiskari, a short way along the coast from the port, at Agios Georgios on the north-east coast, and at coves further along that are easier to reach from the water than from the land. PP swim shorts in Sapphire Blue go into the sea; the shirt stays folded on a warm rock, ready for the walk back up.

Evenings belong to Chora. The few tavernas set their tables in the lanes and small squares of Kastro, the menu follows what the island produces, and nobody dresses for effect. A Vibes Linen Shirt in Dark Blue with PP Casual Linen Trousers in Vanille is as far as he needs to go. The ladies linen set in Sky Blue reads just as well by lamplight, with a light wool layer for the walk home along the ridge, which is always cooler than the port once the sun has gone.

In antiquity the island was known as Oinoe, a name tied to wine, and vines still grow on terraces above the western cliffs. That older, agricultural Sikinos is the one October shows. By the second half of the month the ferry timetable thins and some tavernas close for the winter, and the island returns to its own, slower rhythm. Sikinos is often one stop on a longer route through the southern Cyclades, and the habits of island hopping in linen apply here with a single adjustment: allow for the climb.

From the terrace of Zoodochos Pigi, the afternoon ferry shows first as a white point off the coast of Ios, and there is still time to walk down.

Read more: What to Wear in Folegandros  ·  What to Wear in Ios  ·  What to Wear in Andros