There’s nothing quite like a day spent on the water in Annapolis—the heart of sailing culture and a coastal dream come to life. Whether you’re hopping aboard a yacht for a sun-soaked cruise or dockside with friends, Yacht Day in Annapolis is all about elevated ease and classic American style.

At The Lucky Knot, we like to think of this as our version of a runway. Crisp stripes, windblown white dresses, breezy linens, and nautical accessories make every look feel intentional yet effortless.

For Her: A navy dress, gold hoops, and boat-ready espadrilles (or even better, barefoot).

For Him: Tailored shorts, a fresh polo, and leather boat shoes. It’s about looking sharp, but never overdone.

And let’s not forget the layers. Annapolis evenings can bring a little chill—so a crewneck sweater with anchor embroidery or a quarter-zip in soft cotton belongs in every boat tote. Add aviators, sunscreen, and a good attitude, and you’re ready to take on the bay.

For Her: When the breeze picks up, reach for a classic cable-knit or a soft striped pullover. Perfect over a sundress or with white denim—it’s the layer that ties it all together.

For Him: A crisp quarter-zip or lightweight crew keeps him polished as the sun goes down. Toss it over a polo for a sharp, laid-back look built for boat decks and beyond.

Yacht Day isn’t just a day—it’s a mood. Classic, coastal, confident. Annapolis brings the charm, and you bring the style.