Nantucket in early September is the one destination on this list where you will actually be cold, and packing for it as a beach weekend is the standard error. The days are bright and the water is not, and by eight o'clock on a harbour deck you will want cashmere or a proper cardigan rather than a wrap that photographs well. Town is cobblestone from end to end, which quietly rules out anything narrow or heeled and makes a flat leather loafer the most valuable shoe in the bag. The palette is the easy part: navy first, then white and straw, with almost all the accessory work done in straw. Build the trip around the layer instead of the dress and everything else falls into place. Everything below was in stock this week, most of it arriving within a few days, and a good amount of it is on sale. The other reason to plan this one properly is that the island empties its shops over the holiday and the ferry timetable is not on your side, so anything you forget stays forgotten. Order by Friday morning and pick the fastest shipping offered at checkout.

A navy printed cotton dress is the single most useful daytime piece here, because it works for town, for a lunch and for the ferry without changing. Underneath it, a lined one piece in a blue and white print. Over it, when the wind turns, the navy cashmere that is genuinely the hero of this trip. For shoes, skip anything cushioned and soft looking and buy the leather loafer instead. It is stable on cobblestone, it takes a beating, and it is the reason you will still be walking at the end of the day. Straw carries the accessory story: a raw edge sun hat you are allowed to lose, a structured bucket bag that can sit on a restaurant floor, and a striped tote for beach gear. Two notes on sizing. The navy knit trousers pull on and run close, so take your true size, and the printed dress is cut short, so check the length before you commit. One last thing on the layers. Everything here is built to sit under the navy cashmere, so buy that piece first and let the rest of the bag answer to it.

The boots are not a joke. A low black leather Chelsea boot on a windy September night in Nantucket is more comfortable, more stable on cobblestone and better looking than a sandal you are visibly cold in. If that feels like too much, bring a closed shoe of some kind rather than defaulting to a strappy heel you will not wear twice. We would skip the second straw bag if the budget is tight, because the navy cashmere and the printed dress are what you will actually reach for, and buying accessories to complete a theme is how a suitcase gets heavy. The sale pieces here are real but thin on stock, and the straw tote was down to one when we checked, so treat the discounts as a reason to move rather than a reason to browse. If you take one thing away, pack the navy cashmere first and build the dresses around it. We would also not bother with a second hat. One straw sun hat is enough for three days, and the wind decides how long you keep it anyway.