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Portrait by Henry Raeburn of Alasdair Ranaldson MacDonell of Glengarry in 1812.

Soldiers of the Scottish Division wearing the glengarry on the formation day of the Royal Regiment of Scotland

Glengarry (also Glengarry bonnet or Glengarry cap) is a type of cap which Alasdair Ranaldson MacDonell of Glengarry invented and wears in the portrait to the right: a boat-shaped cap without a peak made of thick-milled woollen material with a toorie or bobble on top and ribbons hanging down behind.

In his "Dictionary of Military Uniform", W.Y. Carman notes that that first recorded military use of the Glengarry may have been that of a piper of the 74th Foot. It is not clear whether earlier pictures of civilians or fencible infantry show a true Glengarry or simply a folded highland bonnet.

Capable of being folded flat the Glengarry became a characteristic part of the uniform of the Scottish regiments of the British Army. By 1860 the Glengarry, without a diced border and usually with a feather, was adopted by pipers in all regiments except the 42nd (Black Watch), who retained the feather bonnet. By 1914 all Scottish regiments were wearing dark blue Glengarries in non-ceremonial orders of dress, except for the Cameronians (Scottish Rifles) who wore dark green, and the Scots Guards who wore peaked forage caps. The diced bands were usually in red and white but the toories could be red, Royal blue or black according to regiment.

For a period from 1868 to 1902 the Glengarry was adopted as an undress cap for ordinary duty and walking out dress for most British soldiers. A cap described in a 1937 amendment to the Dress Regulations for the Army as "similar in shape to the Glengarry" became the Universal Pattern Field Service Cap of the British Army in World War II.

The Glengarry continued to be worn in dark blue or rifle green by all regiments of the Scottish Division up to the amalgamation of all Scottish units into the Royal Regiment of Scotland, as an alternative to the tam o'shanter, particularly in parade dress (when it is always worn, except by the Black Watch, who wore the Balmoral bonnet) and by some regiments' musicians (who wear feather bonnets in full dress). The current type of blue Glengarry worn by the Royal Regiment of Scotland is with a red 'tourie', red, black and white dicing, black silk cockade and the regimental cap badge surmounted by cockfeathers, a tradition taken from the Royal Scots and King's Own Scottish Borderers. Other Commonwealth military forces, who also have Scottish and Highland regiments, also make use of the Glengarry. The Irish Defence Forces also employ the Glengarry and it has been issued since 1922 to all units of the Cavalry Corps and Reserve Army officers. The Irish Glengarry differs somewhat to its Scottish forebear in that the Irish is more akin to a Caubeen with tails. The Glengarry is also commonly worn by civilians, notably civilian pipe bands, but can be considered an appropriate hat worn by any males with Highland casual or evening dress.

In the 1930's, Percy Sillitoe, the Chief Constable of the City of Glasgow Police, replaced the traditional police helmet with peaked caps featuring black and white chequered cap bands based on those featured on the military's Glengarry headress, popularly known as the 'Sillitoe Tartan'. The diced band was subsequently widely adopted by British police forces on their peaked caps.

The correct method of wearing the Glengarry has changed since the end of the Second World War. Prior to 1945, Glengarries were generally worn steeply angled, with the right side of the cap worn low, often touching the ear, and the side with the capbadge higher on the head. The trend since the end of the war has been to wear the Glengarry level on the head.

• British Glengarries - British Army Uniforms and Equipment of World War Two. Brian L. Davis, Arms and Armour Press, London 1983 ISBN 0-85368-609-2
• Canadian Glengarries in the First World War - Khaki. Clive M. Law, Service Publications, Ottawa ISBN 0-9699845-4-5
• Canadian Glengarries in the Second World War - Dressed to Kill. Michael A. Dorosh, CD, Service Publications, Ottawa, 2001 ISBN 1-894581-07-5
• "A Dictionary of Military Uniform". W.Y. Carman. ISBN 0-684-15130-8
• The "Uniforms and History of the Scottish Regiments". R.M. Barnes.

• Clan MacDonnell of Glengarry

See House of Labhran for details on military glengarries. http://www.houseoflabhran.com