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With its historic harbor, cobblestone streets, and a steady breeze off the Chesapeake Bay, Annapolis is the ultimate summer destination for coastal lovers. The town’s signature blend of classic prep and nautical charm isn’t just a vibe—it’s a lifestyle. Whether you’re setting sail, sipping cocktails, or strolling Main Street, here’s your ultimate style and city guide to looking (and feeling) right at home.

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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.

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There’s something about a day on the water that calls for style that’s easy, polished, and just a little bit playful. Whether you’re hosting friends on the boat, heading out for a quick cruise, or relaxing dockside, your outfit should feel effortless and look put-together. From flowy dresses to crisp polos, these are the looks we’re loving for every kind of boat day! 

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There’s something magical about a true American summer—the kind filled with sunscreen, laughter, and timeless traditions. At The Lucky Knot, we believe the best moments happen when you’re doing the simple things in style. Here’s how to embrace the season, the classic way:

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Summer style is all about ease—but easy doesn’t have to mean boring. When you’re reaching for that go-to white sundress or your favorite linen set, the difference between “casual cute” and “chic and polished” often comes down to your accessories.

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