At first glance, Margaret Thatcher and Lilly Pulitzer are worlds apart. One was a grocer’s daughter who became Britain’s first female prime minister and earned herself the nickname the Iron Lady; the other, a Palm Beach doyenne famous for kicky and colorful cotton print shifts worn by Jacqueline Kennedy and C. Z. Guest. Peel away the surface, however, and you realize they’re really cut from the same cloth; both shared a common thread of imagination, determination and drive mixed in with unwavering guts, grit and heart. As leaders, albeit in their own ways, these women embodied true entrepreneurial spirit. Today, we tip our hats off to them and the legacies they leave behind.

Ronald Reagan and Margaret Thatcher, 1986, photographed by Jim Hubbard
Photograph from