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Chipley was born in Columbus, Georgia, the son of Doctor William Stout Chipley and Amelia Stout Elizabeth Fannin Chipley. Chipley's grandfather, the Reverend Stephen Chipley, was one of the founding citizens of Lexington, Kentucky. William Stout Chipley was renowned for his work relating to brain diseases and held two jobs: a professor of medicine at Transylvania University and the warden of the Eastern Asylum for the Insane in Lexington.

Chipley moved with his parents back to Lexington when he was four years old, and was raised for all of his formative years in Kentucky. He graduated from the Kentucky Military Institute and Transylvania University.