Margaret Wood of Essendon, looks thoughtful while reading in her skimmer, highlighted by roses. Melbourne Cup, Flemington. 1964. Substantial prizes are awarded for the best dressed men and women, and the requirement of a hat or fascinator are part of the fun. In 1965, model Jean Shrimpton captured the world’s attention by wearing a miniskirt to a raceday and competition for similar attention continues to be fierce.