We’ve been counting down the days to our big trip of the summer: the better part of three weeks abroad, most of it spent by the water, moving between a few different stretches of coast and a couple of islands. On the itinerary: relaxed dinners that run past sunset, chill mornings, a lot of swimming, and afternoons where nobody checks the time.

Packing for a trip this long is a project in itself. Everything that made it into the suitcase had to be smart and intentional — dresses that pull double duty from boat to dinner, layers for days where there’s a breeze, and of course, a few statement styles that bring me joy. Find the full edit of everything that actually made the cut below!

Cristiano Marcheli Kaftan, Janesso Leone Hat, Celine Sunglasses (old, similar here and here)

There is no piece I return to more in summer than a kaftan. I wear one at home while working, pack one for every trip, and love knowing it can go from a morning by the pool to dinner later that evening without missing a beat. It has the breezy appeal of a cover-up, but the right version feels every bit as worthy of a reservation.

Natalie Martin Dress

Naturally, it’s the color and pattern that make one kaftan stand out to me over another. An all-over palm print, graphic stripe, richly colored paisley, saturated silk, or fringe that adds movement gives an otherwise casual silhouette a sense of occasion. Worn with a wide-brim hat and flat sandals, it’s perfect for an afternoon in the sun, and once it’s time to head to sunset cocktails, a sculptural earring, layered necklace, or smaller bag carries it beautifully into the evening.