Bloomingdale's is where I go for the affordable end of this without it looking cheap. The AQUA Watercolor Guest of Maxi Dress at 118 dollars has the right kind of print for golden hour, and the FARM Rio Rococo Flowers Maxi Dress at 132 dollars is bold in a way that photographs well against sand and water. If you want something quieter, the Eileen Fisher Striped Cotton Gauze Maxi Cami Dress at 92.12 dollars is soft, breathable, and forgiving if dinner runs long and you are still in it at midnight.

Saks is where the fabric upgrade actually shows. The STAUD Allyson Printed Strapless Maxi Dress at 297.5 dollars holds its shape without ever feeling stiff, and the Ulla Johnson Ida Gathered Seam Maxi Dress at 650 dollars has the kind of gathered seam detail that hides a post dinner second plate. The Self-Portrait Gathered Jersey Maxi Dress at 650 dollars is the one I would pack if the trip includes more than one event, since jersey travels without creasing, and it still looks dressed even after a long flight in a carry on.

My honest take is that strapless maxi dresses are the easiest silhouette here, but they are also the ones most likely to need a slip underneath if the fabric is thin, so check the lining before you buy either the AQUA or the Acler options. The mistake people make with beach cocktail dressing is going too formal, structured bodices and boning have no place near sand, they just look uncomfortable in every photo. Spend the money on fabric that drapes rather than on beading or hardware, since neither survives salt air well. If you take one thing away, buy for movement first and print second, everything else is secondary.