Bowles was born in Greensboro, North Carolina. His parents are Jessamine Woodward Boyce Bowles and Hargrove "Skipper" Bowles Jr.. Bowles grew up in Greensboro and graduated from Virginia Episcopal School. Then he studied at University of North Carolina at Chapel Hill, where he was a member of the Zeta Psi fraternity. He graduated with a business degree. He was in the United States Coast Guard for a short time. Next, Bowles studied at Columbia Business School. He earned an MBA. After graduation, Bowles worked for the financial firm Morgan Stanley in New York City.