Besides Vogue, he contributed covers to House & Garden magazine (another Condé Nast publication) around the time of the Great War, before moving to Paris. He also painted North African scenes that fail to impress me. You can Google on his name to locate some of these if you are curious.
Woodruff was not a great fashion illustrator, but was good in the context of his times.
House & Garden cover - June 1917
A nice composition in synch with the architectural style.
House & Garden cover - November 1917
Sketch of Chanel costume - 1923
Vogue cover - March 1926
Interesting minimalist concept.
Wedding dress by Jean Patou - 1926
Fashion illustration - 1926
Vogue cover art - January 1928
Woodruff's best-known work.
Pen & wash illustration - Vogue - May 1929
Franklin Simon hat - Vogue - December 1931
By the 1930s, Deco geometry was out and flowing lines were in.









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