James Steel Maitland was born at Strone, Argyllshire, on 27 August 1887, of a well-connected family, his mother Kate Coats Steel being an adopted sister of the thread magnate George H Coats.
Maitland was educated in Greenock and then Glasgow High School. He had hoped to become an artist but parental disapproval resulted in his being articled to William Leiper, then practising in partnership with William Hunter McNab, in 1903, and was Leiper's last apprentice. McNab was then gradually taking over the practice c.1905-06 as Leiper went into semi-retirement, but Maitland continued to enjoy Leiper's friendship and was frequently invited to stay at Terpersie. During his time at Leiper's, Maitland attended Glasgow School of Art, from 1904 under Eugθne Bourdon. At the School, then in Rose Street, his particular friends were Andrew Noble Prentice and the sculptor Albert Hodge, but the latter moved to London c.1903.
At the end of his apprenticeship in 1909 Maitland went to London where he worked on the British Museum as an unpaid assistant for two years. From there he moved on to a practise in Canada.