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Loft Pleated Side Tie Strappy Midi Pocket Dress ($60, originally $100)

Whether you're boarding a sailboat or eating lobster rolls at cocktail hour, it doesn't mean you can't still look chic. This tiered, strappy midi dress from Loft is a comfortable option to achieve the nautical vibe, and can easily go with any shoe — from espadrilles to your favorite white sneaker. It also comes in black for the committed minimalists.