Drawing upon his interest in both modernist literary movements and medieval architecture and pageantry, Winkfield has collaborated with many contemporary poets and writers, including John Ashbery, Harry Mathews, James Schuyler, and Ron Padgett.
Born in Leeds, England in 1944, Winkfield had an early interest in medieval heraldry and pageantry that had a major influence on his later work.
At the age of sixteen, Winkfield enrolled at Leeds College of Art, which he has described as "a second kindergarten, with no classes to attend (or at least very few) ... everyone was very friendly, a real community.
"[1] Winkfield has described himself as a "self-taught" painter, viewing his painting as a reaction against the Bauhaus-inspired orientation of the school at the time.
Described as a “connoisseur of the original, spare, and strange,”[2] Winkfield has collaborated with John Ashbery, Harry Mathews, Kenward Elmslie, Barbara Guest, Ron Padgett, and John Yau.