McEnany was born on April 18, 1988, in Tampa, Florida, and was raised in Tampa. She is the daughter of commercial roofing company owner Michael and Leanne McEnany. McEnany attended the Academy of the Holy Names, in Tampa. She majored in international politics at Georgetown University's School of Foreign Service, and she studied abroad at St Edmund Hall, Oxford. At Oxford, she was taught by future British Labour politician Nick Thomas-Symonds. After, McEnany spent three years as a producer on the Mike Huckabee Show.

McEnany attended the University of Miami School of Law for one year before transferring to Harvard Law School after completing her first year at the University of Miami. At the Miami School of Law, McEnany was a recipient of the Bruce J. Winick Award for Excellence, a scholarship awarded to students in the top 1% of their class. She graduated from Harvard in 2016.

Despite all this obvious attention and acclaim... there are no childhood photographs