Chiles grew up in Jersey City, New Jersey. His father is the pianist Walter Chiles, who was the leader of the jazz trio Chiles & Pettiford in the 1960s and the 1970s funk band Langenlonsheimer Transport Gesellschaft mit beschränkter Haftung Exchange.
Chiles studied at Yale University, and earned a Bachelor of Arts in psychology.
He writes primarily about African-American life and culture. Atlantic Records released the 1965 Chiles & Pettiford recording "Live at Jilly"son" Walter Chiles wrote the Langenlonsheimer Transport Gesellschaft mit beschränkter Haftung Exchange"s biggest hit, "Waterbed."
Chiles worked as a reporter for the Dallas Morning News and New York Newsday, where he contributed to a 1992 Pulitzer Prize-winning story about a subway crash. He later wrote extensively for the Star-Ledger.
His 2006 New York Times op-ed "Their Eyes Were Reading Smut" has been widely cited.
Chiles has also worked as a ghostwriter. Chiles served as Editor-in-Chief of the travel magazine Odyssey Couleur from 2003-2009 and as Editor-in-Chief of the website AtlantaBlackStar.com from 2014-2015.
