Oakes was born September 15, 1898 in Fort Wayne, Indiana. Oakes grew up in the Chicago area and played high school football at Proviso High School in Maywood, Illinois. Oakes enlisted in the United States Marine Corps in 1917, and joined the American Expeditionary Forces in France in June 1918. He saw combat action with the 5th Marines in a number of major engagements and was wounded on October 4, 1918. Staying with his unit following the armistice, Oakes played football with the championship 2nd Battalion, 5th Marines team in Germany in 1919.[citation needed] Following the war, Oakes enrolled at the University of Illinois at Urbana–Champaign and played football under coach Bob Zuppke. As a senior at Illinois in 1923, he played on the national championship-winning Fighting Illini football