American artist Jane Byrd McCall Whitehead (1858-1955) and her English husband Ralph Radcliffe Whitehead (1854-1929) are best known for co-founding the Byrdcliffe Art and Crafts school and colony in Woodstock, New York, which was active from 1903 into the present. Long before Byrdcliffe, however, the Whiteheads formulated plans for an "art convent" founded on principles of the simple life movement. A rejection of repressive social mores and materialistic behavior and a critique of social inequality in the modern world, the Whiteheads' simple life was enacted in rural places where nature served as a model for spirituality and aesthetics in art and the built environment, and where handwork in the form of art and craft and working the land were balanced with intellectual activity, leisure time and socializing in order to improve physical and psychological well being. This dissertation uses the wealth of primary source material on the Whiteheads--their personal papers, photographs documenting their lives, arts and crafts by them and their circle, built environs and landscapes--to trace the evolution of simple living as it was holistically expressed in the lifestyle and environs they constructed in their early years abroad; their first attempt at simple living as a married couple at Arcady in Montecito, California; and finally, their mature expression at Byrdcliffe in Woodstock, New York. Incorporating an interdisciplinary methodology involving a material culture approach that looks at the man-altered world as evidence for social and cultural history, this is the first scholarly effort to explore what simple living meant and looked like to these particular individuals, and the first project to look at the interconnectedness of simple living on a bi-coastal United States and trans-Atlantic scale between 1870-1930. It also seeks to restore an understanding of Jane's contributions to the simple life environs and art schools she formulated collaboratively with her husband, which were previously attributed solely to Ralph.