Graduating in 1917 from Cornell’s College of Agriculture, where she studied landscape architecture, Cautley worked for Warren H. Manning and then architect Julia Morgan. She opened her own practice in New Jersey and, in 1921, designed the 30–acre community park, Roosevelt Common, in Tenafly. In 1924, she was hired by Clarence Stein and Henry Wright, the developer-philanthropists backing the Garden City movement. With them, she worked on Sunnyside Gardens, Phipps Garden Apartments, and Hillside Homes, all in New York City, and on Radburn, in Fairlawn, New Jersey. Cautley is credited with the selection of native plants for these projects, creating interior common spaces onto which homes and private gardens were oriented, and working to enhance a sense of community through landscape features.
Cautley lectured at Columbia University and the Massachusetts Institute of Technology, and worked with the Civilian Conservation Corps in New Hampshire. She wrote for numerous magazines and authored the treatise, Garden Design: The Principles of Abstract Design as Applied to Landscape Composition in 1935. She earned her M.A. in 1943 from the University of Pennsylvania, where her thesis focused on renovation methods for blighted areas of Philadelphia.