Harry (Hilary) Douglas Clarke Pepler was born on January 14th, 1878. His father, George Henry Pepler, who came of an old Wiltshire family, was a partner in Messrs Diplocks, Brewers, of Eastbourne. The family were Quakers, and Hilary and his brother (now Sir George Pepler) were educated at Bootham School, York. At the age of fourteen Hilary was apprenticed to Sir Reginald Hanson, Bart., as a Merchant Taylor in London; but after a time he entered the tea trade. Then followed a post with a firm of wholesale grocers in Cannon Street. With £250 inherited from his grandfather, he next bought a pewterer’s business and set up as a maker and caster of pewter, employing eight men. But his machines were out of date and eventually he sold the business to a competitor from the United States. During this time he shared rooms in London with Harry Mennell (one of the Quaker branch), through whom he became very friendly with the children of Wilfrid and Alice Meynell at Palace Court, where he often saw Francis Thompson.

In 1903 Pepler met Clare Whiteman, who was studying art under Herkomer at the Bushey School of Art, and they were married in the following year. For some reason, he then decided that his vocation was land surveying, and after his marriage he spent a year at Tunbridge Wells learning this business. His own comment, in some manuscript reminiscences, is: ‘Good heavens, I was a rolling stone’.