Fifty years ago, President Kennedy created the President’s Commission on the Status of Women (“Commission”) to conduct a comprehensive analysis of the status of women in America and produce recommendations for advancing women in the workplace and throughout society. Significantly, the Commission began its report with the topic of education. At the time, women were a minority of students on college campuses and a small fraction of students in business, law, and medicine. Educating women was viewed as a logical way to effect change and open doors for women in the workplace. Today, women make up a majority of college students and nearly half of students at professional schools. Yet in some areas, including women’s inclusion in science, technology, engineering, and mathematics, we still fall short. As a participant in the 1963 Commission, the American Association of University Women (AAUW) is especially pleased to participate in this retrospective of the Commission’s work. This paper begins with educational conditions in the 1960s and then focuses on the most notable educational gains and shortfalls of the past five decades. The impact of women’s educational gains on occupational choice and pay are explored, followed by a discussion of the role of public policies in these educational advances. The paper concludes with new and old challenges facing girls and women, including the rising costs of higher education and the underrepresentation of women in science, technology, engineering, and mathematics.