Winnie was raised in Clifton, Bristol, one of 8 surviving children. One of her siblings Victoria (later Lidiard) became a prominent suffragette - and much of what we know of Winnie comes from biographies of Victoria.
Their father was a furniture dealer and traditionalist. He was unable, however, to combat the influence of his progressive wife. Mrs Simmons was frail - she had 12 pregnancies, but assertive. All the Simmons sisters became suffragettes, after hearing Annie Kenney speak in Bristol in 1907. They were motivated not only by the prospect of the vote but also better education for women and an end to the white slave trade. Victoria remembered being educated in a Dame School and 'asking too many questions.'
Winnie may have joined Victoria on protests and campaigns in Bristol. This included chalking pavements, selling the Suffragette newspaper and making speeches. During one event, a docker told Victoria to get back to the kitchen and bedroom, where she belonged. In March 1912, Victoria and Winnie travelled to London. Victoria took part in the WSPU window smashing campaign and was arrested and imprisoned in Holloway. Every night, Winnie stood on the street outside the prison and shouted encouraging messages to her sister.
Winnie planted a Holly on 5 March 1910.
It is possible that Winnie went to London with her sister during World War I to run a guest house with Victoria in Kensington, catering for professional women. They spent the weekends making shells in Battersea.
Both Winnie and Victoria lived long lives. Winnie was alive in 1979 when she wrote the foreword to Beatrice Wilmott Dobbie's book A Nest of Suffragettes in Somerset and Victoria lived to the age of 102, dying in 1992, the last suffragette.