Montauk over Labor Day asks for less than you think, and the mistake is packing as though it were the rest of the East End. The town runs on surf, sand and a short walk between the water and wherever you are eating, so the pieces that work are the ones that do not mind getting wet, sandy or sat on. Early September is still warm in the sun, but the wind off Ditch Plains is genuine and the temperature drops fast after seven. That means one real layer, not three optimistic ones. The shape of a good Montauk bag is a black jersey dress that goes over a swimsuit, a flat sandal, a raffia hat that stays on your head, and a linen shirt you can button when the light goes. Everything below is in stock now and can reach you before Friday, which matters more than anything else this week. The last consideration is timing rather than taste. Shops out there are thin on stock over the holiday and the highway west is not a rescue plan, so what you order this week is what you wear.

Start with the swimsuit, because in Montauk it is not just a swimsuit. A cut-out one piece in black reads as a bodysuit the moment you pull jeans or a jersey dress over it, which removes the entire problem of changing. Layer the dress on top: ribbed jersey with side slits dries fast, does not crease in a duffel, and survives a wet suit underneath without announcing it. For the hat, choose a bucket over a wide brim. A wide brim is a liability in that wind and you will spend the day holding it. Keep the shoes flat and keep two bags in rotation, one raffia tote that is allowed to get destroyed and one better bag for dinner. On sizing, jersey here runs close to the body, so size up and let it skim. Order by Friday morning and choose expedited. On stripes, this is a beach town and the stripe is the local uniform, so a striped shirt, a striped suit and a sarong tied at the hip will look at home in a way a busy print will not. Vary the stripe widths across the pieces so they sit together instead of competing.

Montauk is the one trip on this list where spending a lot can actively work against you. Nobody is looking at your shoes on a deck at Duryea's, and a delicate sandal will be ruined by the parking lot. If the budget is tight, put it into the dress and the tote and let everything else be cheap cotton. We would skip the flip flop as an evening shoe, which sounds practical and photographs like you gave up. A low flat sandal with an ankle strap does the same job and holds the outfit together. The one piece we would genuinely fight for is the linen shirt, because it is the difference between leaving the beach at five and staying until eight. If you take one thing away, buy the black jersey dress and try it on over your swimsuit before you pack, because that single combination is the whole weekend. We would also leave the second bag behind if you are travelling light. The raffia tote can do dinner if you are honest with yourself about where you are eating.