This is a work in progress. The plan is to list some of the best military books I've come across. I'm going to break the books down into categories. Most of these will involve the conflict or period covered by the book.

Scottish Military

The Uniforms and History of the Scottish Regiments – Major R.M. Barnes – This is an oldie now but still one of the best and most lively of the histories of the Scottish regiments.

The Scottish Soldier – Stephen Wood – Lavishly illustrated from the National Museums of Scotland collection, this is a thoughtful look at the mythology surrounding Scotland’s fighting men.

History

Cassell’s Battlefields of Britain & Ireland – Richard Brooks – If you have this one, you don’t need any other guide to the battles fought in the British Isles. It’s comprehensive, it’s well researched and it’s well written.
Son of the Morning Star - Evan S Connell - The story of General George Armstrong Custer and the Battle of the Little Big Horn. An excellent evocation of the war between the US Army and the native peoples of the Great Plains in the 1860s and 70s.

Military Fiction

The Dead, the Dying and the Damned – D.J. Hollands – This fictional account of an unnamed English regiment's experiences in Korean War rang very true. I checked Hollands out and he won the Military Cross, the youngest winner in Korea, as a teenage platoon commander with the Duke of Wellington's Regiment. He was also apparently the most decorated National Service man of the Korean War. No surprise then that this comes across as a powerful evocation of National Service men in combat and of what it was like to face swarms of Chinese soldiers on a bleak Korean hilltop.

The Secret Battle - A.P. Herbert – Humorist and social commentator Herbert draws on his own experiences with the Royal Naval Division during the First World War to look at how a brave man can fall foul of the military system.

The General Danced at Dawn and McAuslan in the Rough – George MacDonald Fraser – The lightly fictionalised and often comic exploits of Lt. MacNeill as he serves in a  Highland Regiment in the days shortly after the Second World War. Based on Fraser's own time as an officer in the Gordon Highlanders.

Tunes of Glory – James Kennaway - The clash between two contrasting types of officer for control of a fictional Highland battalion shortly after the Second World War. One a Sandhurst man from a family which has long provided the regiment with officers, the other a product of the Glasgow slums promoted from the ranks during the war. Kennaway had been an officer in the Gordon Highlanders and knows of what he writes.

Sword of Honour Trilogy – Evelyn Waugh – A biting portrait of the life a British commando officer based on Waugh's own wartime experiences. The inspirations for several of the characters are easily identifiable. Good on how difficult it is to be a leader of men.

The Revolt of Gunner Asch – H H Kirst – Set in the pre-Second World War German Army, this tale of military subversion is classic. I won't spoil it by telling you how Asch triumphs over the system by turning it against itself.

Memoirs

 An Ordinary Soldier – Doug Beattie, with Philip Gomm – Ulsterman Doug Beattie tells the story of an army career which took him from private in the Royal Irish Rangers to Major in its successor, the Royal Irish Regiment, serving in Afghanistan. Beattie is a character, a real scrapper, and brings perspective sadly too seldom seen in military books. He certainly didn't trigger my bullshit detector.

Try Not to Cry Sergeant Major - Robert McGowan and Jeremy Hands - Among the first of the books to come out of the Falklands War and one of the best. The two journalists focuses on the stoicism and humour of the British soldier rather than the messy side of the job.

The Recollections of Rifleman Bowlby - Alex Bowlby - One of the most honest accounts of the life on the frontline during the Second World War's Italian Campaign by an ordinary soldier. Bowlby tells his tales of cowardice and bravery with a dash of humour.

Wings of the Wind – Peter Stainforth – The exploits of the 1st Brigade of the famed British 1st Airborne Division as seen through the eyes  of its squadron of Royal Engineers. Stainforth effortlessly evokes the battlefields of Tunisia, Italy and the Netherlands. A worthy companion volume for Lt.-Col. John Frost of the Brigade's 2nd Battalion’s better known, and also highly recommended,  A Drop Too Many.

With the Jocks – Peter White – An excellent evocation of what it was like to be in the meat grinder that was the war in Northwest Europe 1944-45 for the average infantry soldier. White was a platoon commander with a battalion of the King's Own Scottish Borderers. Very few of the men White led into their first battle of campaign, in the Scheldt Estuary in 1944, were still around by the time the platoon reached Germany. The book is based on White's wartime diaries.

Quartered Safe Out Here – George MacDonald Fraser – The author of the Flashman series remembers his days as a private in the Border Regiment during the Burma Campaign. Fraser brings his fellow soldiers to life before the reader's eyes.

With the Old Breed – E.B. Sledge – A college professor looks back on his days as a young marine fighting in the Pacific Theatre. Brutal and uncompromising.

Enemy Coast Ahead – Guy Gibson - The commander of the famous Dambusters raid recounts his experiences earlier in the Second World War as a bomber pilot. This book is interesting because it was written during the war and gives some feel for how a bomber pilot looked on the war.

Contact – A.F.N. Clarke – An officer in the British Parachute Regiment takes an honest look at his two tours in Northern Ireland in the 1970s. The squalor of squaddie life in province is neatly captured.

Rommel?Gunner Who? and Mussolini: His Part in My Downfall - Spike Milligan – Two of the funniest and, surprisingly truest, accounts of life in the field available. Milligan's memories of the whole “camping and heavy equipment” experience never fails to bring a smile. The other books in the series aren't so good, though Hitler: My Part in His Downfall is not bad.

Happy Odyssey – Adrian Carton de Wiart – The memoirs of a much wounded British general and favourite of Winston Churchill. De Wiart is very recognisable as the basis for the fictional General Ben Ritchie Hook in Evelyn Waugh's Sword of Honour trilogy who was always taking about “biffing” the enemy. As with many senior military men De Wiart has a way with words (or the sense to work with a top-notch ghost writer) and this book covering his rise from cavalry trooper to general is an excellent tale well told. It takes all sorts to make a world and De Wiart struck me when I first read this book as someone from a different planet. I found him fascinating.

Soldiering

Morale – John Baynes – A fascinating look at pre-First World War infantry battalion, the 2nd Scottish Rifles, which attempts to explain why it “went over the top” to face almost certain destruction in 1915 at Neuve Chappelle. It went into battle with 900 men and came out with 150 effectives. Baynes was a major in the Cameronians/Scottish Rifles after the Second World War and his father served with the 2nd Scottish Rifles in 1915. As a serving soldier, Baynes knew of what he wrote and as a member of the regiment at the heart of this 1966 classic he knew many of the people of whom he wrote or people who knew the men involved.

Above All Courage – Max Arthur – Arthur does a brilliant job of capturing the mood and atmosphere of the Falklands Campaign. He interviewed more than 200 of the men and women who were honoured for what they did in the campaign and selected 29 to focus on. The tales they tell are varied and often capture the selflessness and humility of the truly brave.

The Anatomy of Courage - Lord Moran – A look at morale; how to break it, how to maintain it. Moran was a front line medical officer during the First World War and later became Winston Churchill’s personal doctor.

The Sharp End – John Ellis – A classic of the “personal experience” genre. Ellis uses first hand accounts of the Allied troops to weave a realistic and thought-provoking look at how the Second World War was fought.

The Psychology of Military Incompetence – Norman Dixon – Not a text book, but a highly readable treatise on why incompetents can thrive in a military environment.

Mr Kipling’s Army – Byron Farwell – American Byron Farwell takes an affectionate but not uncritical look at the British Army in the late Victorian and early Edwardian period. An excellent collection of military anecdotes.

Blindfold and Alone - Cathryn Corns and Col. John Hughes-Wilson - A sober and insightful look into Britain's 346 military executions during the First World War.This book cuts through much of the ill-informed hysteria which usually surrounds this controversial subject.

The Sharp End -Tim Cook – The first of two-volume history of the Canadian Army in the First World War. Cook expertly weaves the big picture with telling first-hand accounts to create one of the best books about the conflict I’ve seen.

Dead Men Risen – Toby Harnden – One of the best and most balanced books to come out of the British campaign in Afghanistan. Harnden puts the Welsh Guards operations in 2009 under the microscope to create well-rounded account of the modern British Army at war.

Prisoners and Escapes

Boldness Be My Friend – Richard Pape – This must be one of the classic Prisoner of War stories of the Second World War. Pape was a journalist before joining RAF Bomber Command and this is a superb evocation of his life as a PoW, both in camp and on the run during his numerous escape attempts. His eventual return to the UK is ingenious.

The Naked Island – Russell Braddon – I used to take this account of being a prisoner of the Japanese during the World War II with me when I knew my living conditions were going to shit. No matter how bad things got, they were never as awful as what was going on in this book.

If This Be Man – Primo Levi – Heartbreaking stuff from an Italian Jew about his time in a German death camp during the Second World War. Levi survived, in way. The title says it all, how could human beings behave in the way they did, both guards and prisoners.

Special Forces

The Real Bravo Two Zero – Michael Asher - A brave attempt to unearth the truth about on of the most documented missions in British military history. Former paratroop regiment private Mike Asher went to Iraq and spoke to many of the local people caught up in the events surrounding the botched mission. He makes it clear that he knows that he could be being used as a tool of Iraqi propaganda. But the account he gives is far more credible than most. I have heard that some of the incidents recounted in the best known first-hand accounts weren’t mentioned at the debriefings. I’ve always said that to inflict the number of Iraqi casualties sometimes claimed, the SAS men must have been pulling handcarts filled with 5.56mm ammunition with them. Asher perhaps benefited from having a publisher who wasn’t demanding the story be “sexed” up.
 
Sleeping With Your Ears Open - Gary McKay –– An excellent little account of the Australian Special Air Service Regiment from its formation in the 1960s through to its service in Vietnam. McKay, a former infantry officer, did an excellent job in getting members of the regiment to speak to him frankly. The book details some thought provoking differences between the British and Australian approaches to selection procedures. This is not a definitive history but rather a blend of “typical” experiences and some of the highlights of the unit’s time in Borneo and Vietnam.
 

Espionage

A Spy Among Friends - Ben Macintyre - A fascinating look at the world of British arch-traitor and Soviet spy Kim Philby.