When he was sixteen, Winkler emigrated to the United States where he worked his way across county, eventually settling in San Francisco. There in 1911, he enrolled in the Mark Hopkins Institute (now the San Francisco Art Institute). He quickly proved his facility as an artist and was soon engaged making etchings of the city. He went to Europe in 1922, visiting Paris and London, and produced over seventy plates depicting European cities.
Winkler returned to San Francisco in 1930 and soon became engaged in drawing landscape in the Sierra Nevada mountains. His love of the are soon led him to explore other art forms and in 1933 he began carving decorative boxes from the wood he gathered in the mountains. During his long career, Winkler produced over three-hundred etchings, over one-hundred carved boxes, and thousands of drawings. His works were frequently exhibited on both coasts.