Sir Reginald MacLeod of MacLeod was born on 1 February 1847. He was the son of Norman MacLeod of MacLeod, 25th chief of Clan MacLeod and his wife Louisa Barbara St. John, only daughter of the 14th Baron St John of Bletso. He was educated at Harrow and Cambridge. On 17 April 1877, MacLeod of MacLeod married Lady Agnes Mary Cecilia Northcote, the daughter of Sir Stafford Northcote, later 1st Earl of Iddesleigh, and Cecilia Frances Farrer. They had two daughters. In the 1885 General Election he stood unsuccessfully for the Conservatives in Inverness-shire losing the seat to an Independent Liberal. In 1889 he became the Queen's and Lord Treasurer's Remembrancer, an office of the Court of the Exchequer which was originally concerned with the recovery of dues, penalties and debts owed to the Crown. In February 1900 he was appointed the fourth Registrar General, and in this role he presided over the 1901 census. Two years later, he was in August 1902 appointed Permanent Under Secretary for Scotland. He was knighted in 1905. After a further unsuccessful attempt to be elected to Parliament in 1911 he retired from public life and became a director of Shell, the first of several directorships he held. Sir Reginald became 27th chief of Clan MacLeod in 1929 on the death of his elder brother Norman Magnus and died six years later in 1935. His daughter Olive was noted for her journey of 3,700 miles into the heart of Africa to visit her fiancé's grave. The MacLeod waterfalls on the Moa Kabi river are named after her. The famous Fairy Flag of the MacLeod's was mounted by Sir Reginald. An expert from the Victoria and Albert Museum discussed with Sir Reginald the possible origins of the flag, avoiding reference to the supernatural. The chief listened and said, "You may believe that, but I know that it was given to my ancestor by the fairies." Sir Reginald was the laird of the islands of St Kilda in 1930, when the last inhabitants left the islands. In 1931 he sold the islands to Lord Dumfries, later Marquess of Bute.
Succession of the chiefship after his death
Sir Reginald's elder brothers had both died without male issue and his younger brother's only son Iain Breac had been killed in the sinking of HMS Goliath in 1915. As there were, therefore, no immediate male heirs, he was succeeded by his eldest daughter DameFlora MacLeod of MacLeod, 28th chief and first female chief of the clan