Winifred Phillips attended the Liverpool Art Sheds from 1902 to 1905 along with her sister Mary 'Bee' Phillips, after previously earning a degree from Liverpool University in 1902. After the Liverpool Art Sheds, Phillips continued her studies at the Slade School from 1906 to 1909 where she won the Slade painting competition in 1908. During her studies, she took classes in life drawing, modelling and decorative design. Phillips exhibited at the New English Art Club from 1909 to 1915 and taught in London. During World War I, she joined the Voluntary Aid Detachment (V.A.D.) and served in France and Egypt. Winifred and Bee were friendly with the Macnairs and lived on Rodney Street, from where they could easily access the art 'sheds' at the Liverpool School of Art and the Sandon Studios (now the Bluecoat).