Kalymnos made its living from the seabed. For generations the island's men sailed each spring to the waters off North Africa to dive for natural sponges, and returned in autumn; the trade shaped Pothia, the harbour town, its fortunes and its houses. Sponges are still sold along the waterfront, and the island remains a working place first. On an island that still works for its living, dressing well means dressing quietly.

Pothia climbs steeply from its harbour in tiers of houses painted in blues, ochres and pinks, with the church domes catching the light. It is one of the larger towns in the Dodecanese, busy with ferries, fishing boats and cafés where the island's own life goes on regardless of season. A linen shirt and trousers fit in here without comment. The PP Bliss linen shirt with its long sleeves rolled to the forearm, worn with the PP Trousers 100% Linen, carries a man from the ferry to a waterfront lunch of grilled octopus and on to the sponge workshops without a change.

Over the hill on the west coast, the mood changes. Masouri and Myrties look across a narrow channel to Telendos, the steep islet that faces them, and the grey and orange limestone cliffs behind the villages have made Kalymnos one of the most celebrated sport-climbing destinations in Europe. In October, the climbing season is in full swing, and the cafés of Masouri fill with people in chalk-dusted clothing at the end of the afternoon. For those who come for the view rather than the rock, this is the coast for long lunches and evenings watching the sun drop behind Telendos.

The small boat to Telendos leaves from Myrties and takes only a few minutes. The islet has no cars, a handful of tavernas along one waterfront, and pebble coves a short walk from the jetty. This is a day for the PP natural swim shorts, on the boat and in the water, and a light short-sleeved shirt for the walk between coves; at the taverna, PP linen shorts and a shirt left open at the neck carry him through lunch. For her, the ladies linen set suits the taverna and the waterfront, and the PP linen blouse in Sky Blue goes on for the walk back to the jetty.

Evenings on Kalymnos are not formal, but they are not careless either. Pothia's harbour at night is a promenade of families, and a dinner at one of the fish tavernas along the quay asks for a pressed shirt rather than a beach one. A pressed PP Cuba linen shirt with the PP Trousers 100% Linen suits the quay. She might choose the Amelia linen dress shirt in Oyster, with its walnut buttons, and flat sandals for the steep lanes.

The interior is worth a morning. The road north from Masouri runs past Arginonta to Emporios at the end of the island, through hills of thyme and rock where goats outnumber people. In the middle of the island, the old capital of Chorio and the ruined castle of Pera Kastro above it show how islanders once lived away from the coast to avoid raiders. A long-sleeved linen shirt and closed shoes are sensible for the climb up to the castle, which is steep and exposed.

Kalymnos is reached by ferry from Kos, the crossing from Mastichari being the shortest, and has its own small airport. It sits close to Leros, and many visitors pair the two; the Leros guide follows the same quiet register.

The island's sponge boats still tie up in Pothia's harbour, their hulls painted white and blue, and the scent of the sea is in the town all day.

Read more: What to Wear on Kos  ·  What to Wear on Patmos