Oakley began his career contributing to the alternative comics review Deadline Magazine in the 1980s, where he created Fatal Charm with D'Israeli.
Since then Oakley has contributed to several anthology titles, such as Negative Burn and The Big Book of Urban Legends, even drawing an issue of Neil Gaiman's legendary Sandman.
The series revived many long forgotten UK comic book characters such as the Steel Claw and Grimly Feendish, some of whom had not been in print since the 1950s.
In 2007 he illustrated an adaptation of Edgar Allan Poe's "The Fall of the House of Usher" written by Dan Whitehead and published in Self Made Hero's Nevermore anthology.
Studios' Cthulhu Tales #2 (published April 2008) featured a story entitled The Hiding Place written by Steve Niles and illustrated by Oakley.