Skyler was born and raised in Perth, where he discovered the joy of entertaining a live audience whilst pretending to be a drunk defendant in court during a Year 5 Drama class improvisation. It was from this point of making his classmates laugh that planted the seed of performance. Due to sporting commitments, this was left behind until Year 12, when Skyler had to make the decision of either representing W.A. at the National Basketball Championships for the third time or playing a lead in the high school musical, How To Succeed In Business Without Really Trying. He chose the latter.
After graduating, Skyler quickly became involved in the Perth theatre circuit, starting with Away, where he received a Finley Award nomination for Best Supporting Actor in a play. He also went on to study Contemporary Performance and Theatre Studies in a unique WAAPA and ECU combined course. After completing his second year, he successfully auditioned for NIDA.