Stickley learned basic furniture-making skills in a Pennsylvania chair factory owned by his uncle. After a time he took over the factory, and in 1884 he moved it to Binghamton, N.Y. He experimented briefly with designs in the fashionable Art Nouveau mode before introducing, about 1900, a new line of sturdy oak furniture whose virtues of simplicity, functionality, and soundness of construction were for Stickley an expression of democratic values. He established the Craftsman Workshops in Syracuse in 1901 and began publishing the monthly magazine The Craftsman to carry his ideas and designs to a wider audience. Although he owed much to the British Arts and Crafts movement, Stickley was a highly original designer who applied his ideas not only to furniture but to decorative accessories of all kinds. One of the most popular features of The Craftsman was a series of house designs intended to suit modest incomes, an interest of the Arts and Crafts movement, based as it was on Christian socialism.
The popularity of Craftsman furniture waned after a decade and a half, and in 1916 Stickley ceased publishing his magazine and gave up his bankrupt workshops to two younger brothers, who continued for a time to produce furniture from his designs. Two other brothers had for some time produced similar furniture under the name L. and J.G. Stickley, and numerous other imitators had capitalized on his work as well.
In the late 20th and early 21st centuries, there was a resurgence of interest in Stickley’s designs and ideas. Not only were some of his furniture catalogs reprinted, but illustrated books of his works and a number of monographs were published.