Winslow was born in Berkeley, California and as a teenager he lived in Papua New Guinea. He attended Dún Laoghaire College of Art (now Dún Laoghaire Institute of Art, Design and Technology), Ireland from 1976 to 1980. He then relocated to Baltimore, Maryland. Winslow’s work consists primarily of portraits and murals. His work for private collections has appeared in Style magazine, Luxury Homes, and the Sunday edition of the Baltimore Sun newspaper.
In 2008, Winslow was awarded first prize for a figural work entitled Luke at Johns Hopkins' inaugural National Arts Program Exhibit and Awards contest.