Windley began his career as a journalist and in 1861 formed the Midland Free Press. He was elected to the Borough Council in 1872 and in 1876 became Chairman of the newly formed Sanitary Committee. His leadership was responsible for introducing many public health improvements in Leicester. Windley became an Alderman in 1878 and a Justice of the Peace in 1896. He was Mayor of Leicester in 1899. He was a member of the Leicester Municipal Technical and Art Schools Committee and then the College of Art and Technology Committee. In 1924 he gave £900 to the College of Art to form a scholarship.
The portrait was modelled in 1906 by his daughter Maude Windley, a teacher at the School of Art.