Peaked Service Dress forage cap, Lieutenant Colonel Henry 'Harry' Whitehill (formerly Weisberg), City of London Yeomanry (Rough Riders), City of London Yeomanry (Rough Riders), 1900-1918 (c)

Khaki cloth cap with brown leather chin strap. At centre front, a City of London Yeomanry (Rough Riders) badge. The cap badge of the Rough Riders has the coat of arms, supporters and motto of the City of London, within a circlet bearing the title. 'The City of London Yeomanry', surmounted by a monarchial crown; all within a silver laurel wreath with scrolls bearing the title, 'Rough Riders', and the battle honour, 'South Africa 1900-02'.

The 20th and 22nd Rough Rider Battalions were formed in London for service in the Boer War (1899-1902). The 1st County of London Imperial Yeomanry (Rough Riders) was formed in 1901. The unit's name was changed to the City of London Imperial Yeomanry (Rough Riders) in 1902.

Harry Whitehill (1872-1958) changed his surname from Weisberg after World War One (1914-1918). A veteran of the Boer War (1899-1902), Trooper Weisberg (6416) is recorded in the South African Field Force Casualty List as being slightly wounded at Senekal on 25 May 1900. He was awarded the Distinguished Service Order at the end of World War One, having served at Gallipoli, in Palestine and on the Western Front, with the City of London Yeomanry and on attachment to the Machine Gun Corps. He was confirmed as a Lieutenant Colonel in 1920. Whitehill served in the Home Guard during World War Two (1939-1945).