× How to Dress for the Kentucky Derby Madras Sport Coat. Straw trilby hat. Bow tie. Khakis. Madras sport coat. Derby Casual for the Younger Man. Sport coat. Polo shirt. Pocket square. Khakis. Boat shoes. The Go-To: Sport Coat and Trousers. Navy sport coat. At the derby, accessories make the outfit, so wear a splashy tie and pocket square. Saddle shoes. Light-colored trousers. Light-colored dress shirt. Seersucker suit. Straw hat (Boater, Panama, Milan). Bow tie. Breathable fabric keeps you cool. White or light tan bucks or brogues, or go with a brown/white spectator for extra panache.

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