Floyd entered into partnerships with criminals in the Kansas City underworld after his parole. He committed a series of bank robberies over the next several years, and it was during this period that he acquired the nickname "Pretty Boy." Orville Drake gave him the name because he would wear a white button-up dress shirt and slacks to work in the oil fields. The men on the rig began calling him "Pretty Boy" which was later turned into "Pretty Boy Floyd." According to one account, a payroll master whom Floyd had robbed described him as "a pretty boy with apple cheeks." Floyd despised the nickname.