Anguilla is low, long and pale. The island is coral and limestone rather than volcanic rock, with no mountain to speak of, and its edges are given over almost entirely to beaches — more than thirty of them, some reached by a sandy track, all of them public. That flatness sets the wardrobe: there is little to climb, little to impress, and a great deal of time spent within sight of the water.

The season runs from December to April, when the trade winds are steady and rain is scarce. Days are warm, evenings mild enough that a long sleeve is a choice rather than a necessity. The island is quiet by Caribbean standards; its resorts and restaurants are known for their food and their calm rather than their nightlife.

The island's resort coast runs along its western end. Cap Juluca sits on the long curve of Maundays Bay, its whitewashed villas facing the sea; Malliouhana stands on its bluff above Meads Bay; the Four Seasons lies between Barnes Bay and Meads. The dress at all of them is relaxed by day. A Cuba Linen Shirt in Orange or Blue, worn open over the PP natural swim shorts in Sapphire Blue, takes a man from the sunbed to the beach bar. For the walk to lunch, PP linen shorts in White and the same shirt, buttoned, are enough.

Shoal Bay, on the north-east coast, is the island's most famous beach: a long arc of powder sand and shallow water, lined with low-key beach restaurants. It is a place for a single shirt and swim shorts all day long. Sandy Ground, on the other side of the island, is livelier, with its salt pond behind and its beach bars on the bay; on a Sunday afternoon, live music drifts from the waterfront. A Laos Short Sleeve Linen Shirt in Lemon Yellow or Coral Orange suits its colour and its noise.

Evenings are where Anguilla asks a little more. Resort dining rooms that are casual at lunch often expect something smarter at night, without ever approaching formality. Long trousers are usually expected. PP Casual Linen Trousers in Vanille or Sapphire Blue, with a Male Linen Shirt in White, is the evening at its simplest; the Bliss Linen Shirt in Pink or Sky Blue adds colour without effort. The Monte-Carlo Male in Oyster, with its walnut buttons, is the shirt for the island's more serious tables.

Anguilla's national sport is boat racing, and the island's regattas, with their locally built wooden sloops, draw crowds to the shore in summer and during holidays. Watching from the beach is the right way to see them, in a short-sleeved shirt and shorts, with something to shade the eyes.

Linen suits a man on this island because of its restraint as much as its comfort. In steady heat and humidity, a loose linen shirt lets the breeze reach the skin and dries quickly after a swim; it also has a matte, natural texture that sits quietly against white sand, where shinier fabrics look out of place. The PP natural swim shorts are linen too, so the whole day can be worn in one natural fibre.

St Barts and St Martin are a short crossing away. The wardrobe travels well between them, though St Barts asks for a slightly sharper evening, as our guide to St Barts for men describes.

Read more: What to Wear in Anguilla  ·  The Best Linen Brand for Anguilla