 She stayed on at Bowman for two years under John Brand, specialising in labour law and land rights and representing COSATU, NUM, NUMSA and the Black Sash.In 1985, O'Regan went to London to do a PhD at the London School of Economics on interdicts restraining strikes.On her return to South Africa in 1988, she worked at the Labour Law Unit and then became an associate professor at the University of Cape Town.