Herbert Colborne Oakley was the second child of Richard Garrett Oakley and Maria Oakley. It would appear that he enjoyed the benefits of a financially well-endowed family. His father, who was listed as a "Seedsman And Fruiterer" in the 1881 British Census, became mayor of Southampton in 1908. He was apparently much respected, being referred to by a Southampton Justice Of The Peace as a man "... who was generous and kind towards every good thing in town". The Oakley family were partners in Oakley and Watling, a prestigious Southampton company that was a supplier of fruit, vegetables and flowers to amongst others, the Royal Yacht Britannia and to the Titanic prior to its ill-fated voyage. Before the Titanic left its Southampton dock, it had been supplied with 36,000 apples, 16,000 lemons and 13,000 grapefruit. All the meals on board the Titanic were prepared using fruit and vegetables supplied by Oakley and Watling.
Herbert C. Oakley received a considerable education in the arts. He attended the Hartley Institute in Southampton, (today part of the University of Southampton), where he was a prize winner in 1889. Later, he was a student at South Kensington, in London, in what was then the "National Art Training School", which evolved into the Royal College of Art in the late 1890's. In 1896, at the age of 26, he was awarded a number of prizes for his work there, as documented in the "The Studio"" and "The Artist"" magazines of that period. Having retired, in the early 1910's, he traveled extensively, France and Italy held special appeal for him, probably related to their artistic heritage. He, like most serious artists of that period, felt the need to at least experience if not immerse himself in the culture that continued to spawn the greatest artists the world had ever known. Another probable reason was his desire to travel - and to obtain some respite from winters in Britain. He was fluent in French and reasonably fluent in Italian.
Approximately a decade later, in the early 1920's, he settled in St. David's, Wales, though he would continue to visit, almost annually over the next 15 years, his favorite places in France and Italy.