Referred to as "Britain's premier marine artist of the later Victorian & early 20th century", Wyllie composed his artistry in the face of intense observation by the established English art world. He was born into a family of London painters in 1851. His father, William M. Wyllie, was a genre painter and his brother, Charles, was also accomplished in marine art. (His own son Harold later became a success in marine art.)
Studying first at Heatherley's art school, his obvious natural talent was matched by his ambition and drive. He began to study at the Royal Academy in 1865. He was 17 when his first canvases were exhibited; one of which was purchased by the academy itself because "it was bound to acquire additional historical value", being the early work of a recognizably gifted artist.
With his love for the sea, coupled with his unconventional observations and great technical skill, Wyllie painted tugs, barges and anything else that floated before him, often sketching while in a small dinghy. In addition to painting marine narratives which show the influences of both Turner and Constable, he depicted several events of World War I. He gained wide acclaim as an illustrator and print maker as well, and he considered a large oil panorama of the Battle of Trafalgar, the exhibit of which was ceremoniously opened by King George V, as his crowning achievement. He was also involved in the restoration of the H.M.S. Victory.