Stirling was a successful child model represented by Wilhelmina/New York City and Ford Kids/Los Angeles agencies. He began his modeling career at the age of 6 months old. On his first job he portrayed baby Elvis for an article titled "Cloning Elvis" in Gentlemen's Quarterly. He also modeled for Tommy Hilfiger, Matha Stewart Kids Magazine, Saks Fifth Avenue, FAO Schwartz, Disney and numerous other publications and advertisements.