Born in New York City into a family long active in the arts, Woolf was a portrait artist and printmaker. He studied at the Art Students League and at the National Academy of Design under Kenyon Cox and George deForest Brush. He is best known for his portraits, some commissioned by Collier's magazine, and others paired with interviews that appeared in The New York Times in the 1920s. Wolf served as an artist-correspondent during both World Wars I and II. His work was widely exhibited and resides in the permanent collections of numerous public and private institutions. He died at New York City.