Increasingly, females are taking the helm as president of colleges and universities in the United States, yet men still hold the majority of presidential positions (ACE, 2012). The Ivy League is an exception. In the Ivy League, the presidency is held by an equal number of females and males. For three of four Ivy League institutions where females are leading, it is the first time the institution has been led by a woman. This study explored the factors that influenced the career advancement and leadership styles of the four female Ivy League presidents, with insights from three of the four females' former president and mentor/advisor, Dr. Harold Shapiro, President Emeritus of Princeton University. The theoretical framework for the study includes Bass' (1999) theory of transformational leadership where leaders challenge assumptions, seek change, encourage creativity, and display behaviors of collaboration; Donovan's (2006) liberal feminist theory that suggests education engenders democracy; Chafetz' (1997) cultural feminist theory, a form of radical feminism that embraces the distinct differences between males and females; and Epstein's (1999) generativity theory, where he posits that newness is a hallmark of creativity; among others. This study used a descriptive mixed method, case study approach. The factors that have influenced the four female Ivy League presidents' careers and their insights into their leadership styles were compared from online video interviews, printed interviews, and a face-to-face interview with Dr. Shapiro. The results suggest that the four female presidents exhibit strong behaviors in transformational leadership styles; that their careers were influenced by their ability to be creative, both personally and professionally; and influences from family members, former teachers, colleagues, and their own self-efficacy, which advanced their efforts to make a difference and effect change. Females who aspire to become presidents of institutions of higher education can learn from the factors that influenced the careers of the four Ivy League female presidents. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]