After serving in the military during Second World War, Woolf settled in the Los Angeles area where he worked at a local decorating store. He met John Woolf in 1948 and together their homes created a distinctive style using Mansard roofs, Doric columns, oval lead windows and shutter-framed French doors. Inside, the space was typically as glamorous as it was a play on illusion with circular hallways and mirrored pool pavilions.
Their clients included many of the leading entertainment personalities of the day including George Cukor, Katharine Hepburn, Ira Gershwin, Judy Garland, Bob Hope, Fanny Brice, Cary Grant, Lillian Gish, Ray Milland and Loretta Young.
Shortly after his death in 2004, the lives of all four men were featured in a major article for Vanity Fair.