Charles Gilbert Joseph Holiday was born in London in 1879. He was the son of Sir Frederick Holiday, and nephew of artist Henry Holiday, a painter and stained-glass designer. His mother was a watercolourist. He attended Westminster School, and it may have been during his time there that he observed at first hand the horses and troops of the Royal Horse Artillery, where he would later serve. Holiday studied at the Royal Academy of Art (1897–1902) and was distinguished for his ability to capture expression and movement, using an array of mediums such as charcoal, pencil, oils, pastels and watercolour. He began to produce commercial illustrations for magazines such as The Strand, The Tatler and The Graphic at the start of the twentieth century, whilst still producing works on canvas with oil paint.