Pettiway holds a doctoral degree in urban geography, at the University of Wisconsin-Milwaukee, 1979. One of his primary research interests is the integration of geographical and criminological theories to explain patterns of crime in urban areas. He is Professor of Criminology at Indiana University, Bloomington.

His work, Honey, Honey, Miss Thang: Being Black, Gay and on the Streets documents the lives of five transgendered black gay men. It and a companion book, Workin' It: Women Living Through Drugs and Crime, were funded by a million dollar grant from the National Institute on Drug Abuse which sought to investigate the relationship betweeen drug use and urban crime.