The assumption that this is a 'prate flag' is not that correct as it seems to be. Although heavily popularized by the books and movies, the 'white skull and crossbones on the black flag' does not seem to be popular choice among pirates, and it possibly became synonymous with piracy only after the mainstream presence of the history of Edward 'Blackbeard' Teach who was most likely using this design as his personal flag . Charles Johnson uses the term 'Jolly Roger' in his book A General History of the Pyrates published in 1724, but the flags he refers to were nowhere close aforementioned design, suggesting that the term 'Jolly Roger' was an already a common name for the pirate flag. It is often pointed out that the term itself is a bastardized French joyeux rouge (merry red) suggesting that the pirate flags in 17th century, when the large number of pirates were French rather than English were red rather than black, what was later adopted also by the English pirates.

We have the accounts of the expedition across the Panama Isthmus in 1680 that was undertaken by the crews of seven pirate ships that eventually attacked city of Santa Maria. The one under captain Bartholomew Sharp used red flag with white and green ribbons, crew of Richard Sawkins used a red flag with gold stripes, two crews under captain Peter Harris had green flags, another two crews under Jon Coxon carried red flags and the crew of Edmund Cooke used a flag with alternating red and gold strips and a white hand holding a sword. Thus, out of seven flags, there were not a single black one, but five were either red or at least partially red.

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Tradition of wearing white or silver skull-and-crossbones emblem in the military traces back to mid-18th century. In 1741, Frederick the Great formed the 5th Hussar Regiment under Mjr. von Mackroth. This unit wore distinctive black uniforms and quickly adopted the skull symbol as its regimental emblem. This tradition was continued after the regiment was expanded and then divided and renamed to 1st and 2nd Lifeguard Hussar Regiments in 1808, at least partially due to their successful exploits during the Wars of Austrian Succession and Seven Years War. In 1813, after the death of Federico Guillermo, Duke of Brunswick-Wolfenbüttel, his soldiers, already wearing distinctive black and green uniforms also started to wear a skull patch on their uniforms, as a remembrance of their commander.

This symbol, was also common among Russian troops, usually light cavalry, where it has been commonly known as the 'Adam's head' (rus. Адамова голова). It could have been adopted from Prussian units, but it could have also evolved independently, as it has also been used by e.g. 17th Lancers (Duke of Cambridge's Own) as a commemoration of its former commander, James Wolfe who was mortally wounded in a victorious Battle of the Fields of Abraham in 1759. Similarly to its Prussian usage, it tended to represent the indifference in the face of death or even acceptance of the mortal threat. It is quite telling that in the Central and Eastern Europe, the practical usage of term 'death' was not unusual among military troops, usually in the names of the units (like 'Zouaves of Death' under François Rochebrune who fought in the January Uprising in 1863-1864) or various mottos, usually along the lines of 'Victory or Death'.

Skull and crossbones has been used during 1812 campaign by one of the Voluntary Petersburg light cavalry regiments. A century later, Nicholas II established the 'crossbones' as an official symbol of the newly formed 5th Alexandrov Hussar Regiment. It also has been used by 17th Don Cosssack Regiment and 4th Mariupol Hussar Regiment. The former gained almost legendary status in pre-Revolutionary Russia due to its exploits under the command of Gen. Yakov Petrovich Baklanov in the Crimean campaign of 1850s. Legend has it that when stationing in Groznoy Fortress (now Grozny, Chechnya) Baklanov received a package from an unknown sender. The package contained a small black regimental flag adorned with the silver skull and crossbones and the closing phrase from the Nicene Creed ('I look for the resurrection of the dead, and the life of the world to come. Amen'). Several other Cossack units were also using a similar flag, notably the cavalrymen of starshina (later Lt. Gen.) Boris Vladimirovich Annenkov who fought under Gen. Kolchaks during Russian Civil War.

The symbol of 'Adam's head' was also quite common among storm units (also commonly known as 'Death's units') during the Great War, that were Russian equivalent to german Sturmtruppen or Italian Arditi who, especially after the Februrary Revolution sometimes took the tasks of barrier troops preventing mutiny and desertion. The best known of these units was the 1st Storm Regiment of the 8th Army, later known as Kornilov's Regiment that took part in the Russian Civil War on the 'White' side, although this particular unit used the skull over crossed swords rather than bones not unlike the actual flag used by a pirate Jack Rackham). 'Adam's head', along red chevrons was also worn by the soldiers of another 'White' unit, 1st Independent Siberian Brigade (similar to this one). Another one is the Revel Marine Storm Regiment formed in Revel (now Tallinn, Estonia) on 18th June 1917 of the sailors from the ships 'Rurik', 'Oleg', 'Bayan' and 'Bogatyr' that used red sleeve chevrons and black shoulder pads with 'Adam's head' as the identifying symbols.

Of note is also the use of the skull and crossbones as the symbol of sacrifice, as was the case of the 2nd Detachment of the invalid volunteers. The red chevron on the left sleeve and the letters 'уд' (rus. 'ударный') indicate that it was a shock (stromtrooper) unit. With the morale slowly decreasing, the idea of forming volunteer line units of crippled but still capable soldiers as well as all-female units were proposed by Gen. Aleksei Alekseyevich Brusilov and Lt. Maria Leontieva Bochkareva. Many of of such units used skull-and-crossbones as the symbol of sacrifice or courage, adopted the name 'Units of Death' and officially pledged to die rather than to withdraw.

The symbol was quite common in Germany also in 20th century. For example, it can be seen on the armoured vehicles used by the anti-Revolutionary units (or 'Troops loyal to government' as they were calling themselves) fighting the Spartakist Uprising in 1918-1919 in Germany. These vehicles included armoured cars, heavy armoured cars, tanks and its equivalents (the latter is a copy of A7V tank with no armamanet mounted). Interestingly, a Kokampf Freikorps Unit used four cars (Austin II and III) that were captured on Russian troops by German army during the war. In Italy, a skull-and-crossbones or, alternatively, a skull with the dagger held in teeth was a common adornment of the 'Black Brigades' or Corpo Ausiliario delle Squadre d'azione di Camicie Nere (Auxilliary Corps of the Black Shirts Action Squads), a paramilitary organization created by the Republican Fascist Party in July 1943 that can be compared with WW2-era German Freikorps. The gold skull-and crossbones, worn on the shoulder pads was used by the 5th Cavalry Regiment of the Reichswehr, and later by the 1st, 5th and 11th Cavalry Squadrons that were again refitted into 5th Cavalry Regiment in 1943.