Natalie Finegar grew up in the Buffalo area of Western New York until she moved to Carroll County, Maryland while in High School. She graduted from the College of Notre Dame of Maryland (now Notre Dame University of Maryland) in 1990.

Natalie attended the University of Maryland School of Law from 1990 to 1993. She received the Hoffberger Clinical Law Prize for her work on criminal defense.

From 1993 to 1994, Natalie clerked for the Honorable Elsbeth Levy Bothe of the Circuit Court of Baltimore City. She then joined the Office of the Public Defender of Maryland where she served in the Baltimore City District for 23 years.