Gladys Windsor Fry and Harry Windsor Fry first met when he was her art teacher in 1906. They married 16 years later. She was a student at Hammersmith School of Art. She also studied with the Horsham-based artist, Florence Davey and with G. H. Catt in Chichester. Fry was a King's Prize winner for design and gained City & Guilds embroidery honors. She wrote two publications and exhibited at the RBA Walker Art Gallery in Liverpool at Festival of Britain in 1951 and in the provinces. She lived for many years at Hove, Sussex and later in Brighton.