After completing the Columbia School of Architecture program and internship with Santa Barbara architect, George Washington Smith, Shepherd moved to La Jolla. Examples of Shepherd homes in Hermosa and the names of the original owners include the Turner home, 391 Via Del Norte; the Searle home, 6209 Avenida Cresta; the original home of Ruth Shepherd, 301 La Canada.
Shepherd designed commercial buildings in downtown La Jolla including the award winning two story store and office building on Wall Street between Herschell and Ivanhoe, in November of 1928. Other contributions include the John Scripps residence, the Marine Room at the La Jolla Beach and Tennis Club. In 1947 Shepherd designed his own home for himself and his wife, Ruth. A tour of the Italianate structure clearly illustrates the Shepherd trademark of utilizing a variety of aesthetically pleasing features, among them the inset shuttered windows and floorplan that faces a walled-in garden courtyard.