Guy Wiggins was born in Brooklyn, New York in 1883 but spent much of his youth in England. The son of Carlton Wiggins, an accomplished painter in the Barbizon style who had studied under the American landscape painter George Inness, Wiggins showed an early aptitude for art. When he was eight, a group of New York critics praised a collection of watercolors he had completed in France and Holland. Initially, Wiggins planned to study architectural draughtmanship and began studying architecture at the Brooklyn Polytechnic Institute in 1900. He soon enrolled in the National Academy of Design in New York City. There, he was taught by William Merritt Chase and Robert Henri.
Wiggins encountered success quickly. When he was twenty, he was the youngest artist to have a work included in the permanent collection of the Metropolitan Museum of Art. He received the prestigious Norman Wait Harris Bronze Medal from the Art Institute of Chicago in 1917 and, in 1919, was elected to full membership in the National Academy of Design in 1919. In addition, he won prizes from the Connecticut Academy of Fine Arts, the Salmagundi Club and the Art Club of Philadelphia. During the 1910s, Wiggins spent most of his time in New York City, where he specialized in painting urban winter scenes. He would become nationally-celebrated for his evocative depictions of New York in winter. He would often execute his paintings while gazing down on the city from a high perch afforded by a skyscraper.