Charles White Whittlesey was born January 20, 1884 in Florence, Wisconsin. He was the eldest son of Frank R. and Annie Whittlesey and had three younger brothers: Russell (b. July 1887), Elisha (b. February 1892) and Melzar (b. July 1893). All of the children were born in Wisconsin but, sometime between 1893 and 1900, the family relocated to Pittsfield, Massachusetts where Frank was employed by General Electric Co., first as a Purchasing Agent and later as a Production Manager.
Whittlesey attended Pittsfield High School and after graduation entered Williams College. While at Williams, he was a member of the Delta Psi fraternity and the Gargoyle Society. He was Editor- in-Chief of the Gulielmensian (the College yearbook), and Editor of both the Williams Literary Monthly and the Williams Record. He contributed to these publications frequently and, perhaps as a result of this prolificacy, was asked to write the essay on the "Literary Enterprises" of the Class of 1905 for the Class Book. His classmates, who nicknamed him both "Count" and "Chick", voted Whittlesey the third brightest man in the Class of 1905.
After his graduation from Williams, Whittlesey attended Harvard Law School, from which he graduated in 1908. He then went into law practice in New York City with the firm of Murray, Prentice & Howland from 1908 to 1911. In 1911, he entered practice with his friend and classmate, J. Bayard Pruyn, at 2 Rector Street, New York City. He remained with Pruyn & Whittlesey until August 8, 1917, when he was placed on active duty and asked to report to Camp Upton in Yaphank, Long Island. Here he received three months of training prior to his term of service in Europe. One year prior to this, in August 1916, Whittlesey had graduated from the military training camp at Plattsburgh, New York.