Winslade was born in Surrey in 1965 and spent a lot of time indoors as a child because of a heart murmur. His main source of entertainment were Marvel Comics such as Howard the Duck and Deathlok. After he attended Birmingham Polytechnic, to study art, he had the idea of working in the comics industry. Here he met Steve Pugh who was already active in comic art.[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.[1] Before that project started he worked on Crisis and Revolver as well as inking Steve Dillon's work on Car Warriors for Epic. 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.