What unspoken messages do First Ladies send with fashion? And how did the unforgettable Jacqueline Bouvier Kennedy break the mold to present her husband's candidacy and presidency as progressive and modern? Sandy McLendon, design historian and editor of jetsetmodern.com, and former contributor and senior editor at Modernism Magazine, takes a visual tour through Jackie's strategic choices: hiring Hollywood costume designer Oleg Cassini; embracing the slim sheath dress and fuss-free pillbox hat (contrasted with Mamie Eisenhower's lacy, girlish selections); and selecting—down to the detail—trim, elegant gowns suitable for superpower diplomacy. McLendon unpacks the elements of "The Jackie Look" so desired by millions of women of the time, and influential to pop culture then and now.