Hawkins was born in Finley, New South Wales to Jack and Jenny Hawkins. He grew up in the New South Wales region of Finley as the middle child among three children. He attended Finley High School and played for the Finley Football Club before making the move south of the border to begin boarding at Melbourne Grammar School. Hawkins' footballing ability was recognised early on when he was selected to play first XVIII football for the school whilst still in year ten, when many of his teammates were completing their final year of schooling at year twelve. Hawkins kicked four goals on debut for the school and his performances up forward soon received attention from AFL recruiting teams. By the time he had reached his final school year he was rewarded with joint captaincy of the football team alongside Hawthorn draftee Xavier Ellis. He was also selected in the Associated Public Schools (APS) team to play the Associated Grammar School (AGS) selected football team in the traditional annual clash of schools, where he won best on ground honours for his performance.