He was educated at the Royal Military College, Sandhurst, and entered the Second Life Guards in 1882, becoming Captain in 1891.
[citation needed] Naylor-Leyland was returned to Parliament for Colchester as a Conservative in 1892, a seat he held until 1895 when he accepted the Chiltern Hundreds.
The latter year he was created a Baronet, of Hyde Park House, Albert Gate, in the County of London.
He was married at St George's, Hanover Square,[3] London, on 14 September 1889[3] (aged 25) to Jeanie[1][4][5] Willson Chamberlain (1864–1932),[4] daughter of Mr and Mrs William Selah Chamberlain, of Cleveland, Ohio, USA;[3][1] they had two sons:[6] His wife's beauty[1] and wit reportedly played a major role in her husband's return to politics in 1898.
They were part of the Prince of Wales's set, with their town house at 60 Knightsbridge, and their country seat at Lexden Park, Colchester.