At an early age, the Estes family moved to Chicago where he studied fine arts at the School of the Art Institute of Chicago between 1952 - 56. He frequently studied the works of realist painters such as Edgar Degas, Edward Hopper, and Thomas Eakins, who are strongly represented in the Art Institute's collection. After he completed his course of studies, Estes moved to New York where for the next ten years he worked as a graphic artist for various magazine publishers and advertising agencies in New York and Spain. During this period, he painted in his spare time. He had lived in Spain since 1962 and by 1966 was financially able to give up the day job.
Beginning around 1967, he began to paint shopfronts and buildings with glass windows and more importantly, the reflected images shown on these windows. The paintings were based on colour photographs he would take, which trapped the evanescent nature of the reflections, which would change in part with the lighting and the time of day. Estes' paintings were based on several photographs of the subject. He avoided using famous New York landmarks. Though called a photorealist I personally think that his paintings have an edgy feel. He uses the language of Edward Hopper - often a deserted urban environment, free of litter, but stuck in another time dimension – I think of them more as photo-surrealist.