A former White House aide to President Bill Clinton, Boykin was raised in St. Louis, Missouri, and attended Countryside High School in Clearwater, Florida, before graduating from Dartmouth College.
After leaving Dartmouth in 1987, Boykin spent a year and a half working for Michael Dukakis' presidential campaign and then entered Harvard Law School, where he was a leader in the campus diversity movement and general editor of the Harvard Civil Rights-Civil Liberties Law Review.