Sidney was the younger of two children, and the only son, of William Sidney, 5th Baron De L'Isle and Dudley (19 August 1859 - 18 June 1945) and his wife, Winifred Agneta Yorke Bevan (d. 11 February 1959). The Sidney family was one of England's oldest and most distinguished families. He was a descendant of King William IV by his mistress Dorothea Jordan. He was educated at Eton and Magdalene College, Cambridge and became a chartered accountant. In 1929 he joined the Grenadier Guards Reserve of Officers. On 8 June 1940 he married Jacqueline Vereker, daughter of Viscount Gort VC and they had 4 daughters and one son.
During World War 2, Sidney served in France and Italy. While serving as a company commander in the 5th Battalion Grenadier Guards, he led a handful of men in the defence of the Anzio beachhead in February 1944, for which he was awarded the Victoria Cross. Sidney led a successful attack which drove German troops out of a gully. Later he led another counter-attack and dashed forward, engaging the Germans with his tommy gun at point-blank range, forcing a withdrawal. When the attack was renewed, Sidney and one guardsman were wounded and another killed, but he would not consent to have his wounds dressed until the Germans had been beaten off and the battalion's position had been consolidated. During this time, although extremely weak from loss of blood, he continued to encourage and inspire his men.
In later life, when asked where he had been shot, he would jocularly respond that he was shot in Italy. This was to conceal the fact that he had, in fact, been shot in the buttocks. The ribbon for the medal was made from one of his father-in-law Lord Gort's uniforms and was awarded by General Alexander on 3 March 1944 in Italy.
In 1944 he was elected as Conservative MP for Chelsea and the following year his father died, elevating him to the House of Lords as 6th Baron De L'Isle. In 1951 he was Secretary for Air under Winston Churchill and visited Australia where he met Robert Menzies. He was created Viscount De L'Isle of Penshurst in 1956 and in that title became Governor-General of Australia in 1961 until 1965. He was the last non-Australian to hold the position. He was appointed Knight of the Garter in 1968 so that his full title was The Rt. Hon. The Viscount De L'Isle VC KG GCMG GCVO PC. He died in Kent on 5 April 1991 and his son Philip became the 2nd Viscount De L'Isle.
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