In May 1908, he created a cover for the magazine that featured his first “fadeaway girl”: a figure whose clothing matched, and disappeared into, the background. Phillips developed this idea in many subsequent covers. In the 1910 example of his work displayed to the right, portions of the figure’s skirt merge seamlessly with the background, yet the edge of the skirt remains easily defined by the viewer.
Phillips’ use of negative space allowed the viewer to “fill-in” the image; it also reduced printing costs for the magazine, as “the novelty of the technique and the striking design qualities masked the fact that Life was getting by with single color or two-color covers in a day when full-color covers were de rigueur for the better magazines”. Phillips worked in watercolor and always painted from life; according to his biographer, Michael Schau, “he refused to work from photographs or to use the pantograph”. His most frequent model in his early years was Teresa Hyde, a nurse whom he met in December 1907 and married in early 1910.
Phillips produced cover art for other national magazines besides Life, including Good Housekeeping, which for two years (beginning in July 1912) made him their sole cover artist. Phillips also created many advertising images for makers of women’s clothing, and for such clients as the Overland automobile company and Oneida Community flatware. His series depicting women wearing Holeproof Hosiery products was considered daring for its time. Phillips’ works also appear in the 1921 and 1922 editions of the U. S. Naval Academy yearbook, Lucky Bag.
From 1905 until his death, Phillips lived and worked in New Rochelle, New York. His work habits were regular; his other activities included raising pigeons, a hobby he had pursued since he was eight years old.
In 1924 he was diagnosed with tuberculosis of the kidney, and he was frequently ill thereafter.In January 1927, when problems with his eyesight made painting difficult, he dedicated himself to writing.Phillips died in New Rochelle of his kidney ailment on June 13, 1927, at the age of 47.