This year, choose between traditional brimmed hats and quirky vintage finds reminiscent of Blair Waldorf in Gossip Girl. No matter your choice, be bold—after all, this is the time of year to make a statement.
Derby Princess If high style is your game, this hat has your name on it. The price isn’t cheap, but the bright color and intricate detailing make this “stargazer” hat an investment piece. Hats in the Belfry, Annapolis; $440.
Black Beauty A simple black style looks classic and chic when paired with a sophisticated sheath dress in a single color. Hats.com; $48.99.