Winslade was born in Surrey in 1965 and spent a lot of time indoors as a child because of a heart murmur.
After he attended Birmingham Polytechnic, to study art, he had the idea of working in the comics industry.
[1] He produced commercial artwork after college before showing his portfolio to Garth Ennis at a comic convention in Coventry, where he got the job drawing Goddess.
During this period he also worked on Elaine Lee's Skin Tight Orbit and was pencilled in as the artist for The Red Seas, with writer Ian Edginton, when it was going to be run by Epic, but he was too busy with Goddess.
He was nominated for the 1996 "Best Cover Artist" and "Best Painter" Eisner Award for his work on Vertigo's Goddess and Vamps: Hollywood & Vein.