Shaw studied at the Harvard School for Boys in Hyde Park Township. He was accepted to Yale University, graduating with a bachelor of arts in 1890. While at Yale, Shaw was the lead editor of "The Yale Record", the world's oldest humor magazine. He was admitted to the Massachusetts Institute of Technology (MIT) later that year. MIT was one of the few architectural schools in the country at that time, closely following the rules set forth by the École des Beaux-Arts. Shaw completed the two-year program in one year. Shaw would use the elements of Georgian, Tudor, and neoclassical design he learned from MIT in most of his later works.