Captain Harry Lawrence Oakley was born in York on 28 December 1882, the son of a chemist and alderman of the city. He showed an aptitude for art, and for paper cutting, at an early age and attended art schools in York and Leeds as well as the Royal College of Art in London.
While teaching art for London County Council and then Worcester Royal Grammar School, Oakley moved towards silhouette art. After a well-received exhibition in York and a stint running his own temporary studio in London at the Army and Navy department store, he decided on a career as a silhouettist.
Oakley joined the 8th Yorkshire Regiment (the Green Howards) during the First World War, along with two of his brothers. Early on, he designed a silhouette recruitment poster, “Think!”, which was adapted into several versions, including one for the Navy.
Oakley also began to send back charming, expressive and often humorous silhouettes depicting life at the front, which were published in The Bystander. Wounded in 1916, he was appointed ADC to the Commanding Officer of the 32nd Division. After the Armistice, he continued to send back silhouettes depicting scenes from the occupation of the Rhineland.
His post-war career was busy and varied. He divided his time between portraiture, magazine and commercial projects, designing advertisements for Selfridges and L.N.E.R. among many others. His magazine work often included a full-page silhouette for Holly Leaves, the Christmas number of The Illustrated Sporting and Dramatic News.
During his lifetime, Oakley cut literally thousands of silhouettes and captured the likenesses of many famous personalities, including the Prince of Wales and the tennis champion Suzanne Lenglen.