Completing his undergraduate training by the end of 1929, Oakes submission for the annual Tite Prize, conducted by the Royal British Institute of Architects, drew an honourable mention.

[5][6] Under the stewardship of former student, British archaeologist Ian Richmond, Oakes would thrive in Rome and be granted an extension to his stay for an additional year.

In 1933, Oakes returned home to a work alongside his father at the Middlesex County Council, whilst also teaching part-time at the Architectural Association.

That same year he was awarded first honorary mention in the Croydon Civic Centre Competition in collaboration with Maxwell Allen, and received the Arthur Cates prize for his design for The Promotion of Architecture in Relation to Town Planning.

[7] Within two months of arriving, he took on the acting Government Architect role, on account of his predecessor taking ill. During his time in Bengal, Oakes actively designed and administered numerous public projects ranging from the expansion of Dum Dum Jail, the Custom House in Calcutta, Technical Colleges in Dacca and Chittagong along with hospital wings, postal and police stations throughout West Bengal.

As a member of the Royal Artillery, he was attached to the 72nd Indian Infantry Brigade of the 36th Division, under the overall command of the 14th Army, led by Field Marshal William Slim.

It would take two years of intense fighting in the jungles and mountainous terrain, culminating in the Battle of the Ngakyedauk Pass by 3 May 1944 to stop the march on Delhi by the Japanese.

Within two months, upon the recommendation of Sir Frederic Kenyon, Oakes would take up an appointment as Advisory Architect to the Imperial War Graves Commission.

And over the next seventeen years, he oversaw a modernist architectural program of numerous office buildings, laboratories, retail outlets and factories throughout the United Kingdom.