Many people have engaged in cross-dressing during wartime under various circumstances and for various motives. This has been especially true of women, whether while serving as a soldier in otherwise all-male armies, while protecting themselves or disguising their identity in dangerous circumstances, or for other purposes.
Conversely, men would dress as women to avoid being drafted, the mythological precedent for this being Achilles hiding at the court of Lycomedes dressed as a girl to avoid participation in the Trojan War.
- Epipole of Carystus was a Greek woman described by Chennos as having joined the Greek army during the Trojan War.[clarification needed]
- Achilles was a Greek hero in the Trojan War. After hearing from an Oracle that her son would die in battle, his mother, Thetis, hid him in woman's clothing to prevent him from being taken to war.
Early Middle Ages
- Hua Mulan was, according to a famous Chinese poem, a woman who joined the Chinese army in her father's stead.[clarification needed]
- Joanna of Flanders (c. 1295–1374) led the Montfortist faction in Brittany in the 1340s after the capture of her husband left her as the titular head of the family. She wore male dress at engagements such as the siege of Hennebont.
- Onorata Rodiani (1403–1452) was an Italian mercenary who served as a cavalry soldier, disguised in male clothing and with a male name, under a condottieri (freelance commander) named Oldrado Lampugnano beginning in 1423.
- Jacqueline of Wittelsbach, Countess of Hainaut, Holland and Zeeland (1401–1436) led the Hoek faction (the aristocratic faction) in Holland. Jacqueline and one of her servants disguised themselves as soldiers to escape confinement in Ghent.
- Joan of Arc (1412–1431) is a folk heroine of France and a Roman Catholic saint. A peasant girl born in what is now eastern France who claimed divine guidance, she led the French army to several important victories during the Hundred Years' War. After being captured by her enemies, she was burned at the stake for heresy when she was 19 years old. She journeyed through hostile Burgundian territory disguised as a male soldier.
- Brita Olofsdotter, widow of soldier Nils Simonsson, dressed as a man and enlisted in the Finnish unit in the Swedish cavalry in Livonia. She was killed in battle, and King John III of Sweden ordered her salary to be paid to her family.
- Catalina de Erauso (1592–1650), the Nun Lieutenant, was a semilegendary Spanish adventurer.
- Aal de Dragoner (died before 1710), served as a Dutch dragoon. After death her body was put on display in an anatomical theatre.
- Christian Davies (1667–1739), "Mother Ross", served in the 2nd Dragoons (Scots Greys).
- Louise Antonini (1771—1861) was a French woman who disguised herself as a male to join the French Navy during the revolutionary period and the Napoleonic wars.:168
- Bonnie Prince Charlie (1720–1788) dressed as Flora MacDonald's maid servant, Betty Burke, to escape the Battle of Culloden for the island of Skye in 1746.
- Chevalier d'Éon (1728–1810) fought with the French dragoons during the Seven Years' War. In 1777 d'Éon began dressing full time as a woman and lived as such until death. When d’Éon died in London in 1810, the body was examined by physicians and discovered to be genitally anatomically male.
- Francina Broese Gunningh (1783—1824) was a Dutch soldier, in service of the French, Prussian and Dutch army.
- Phoebe Hessel (1713–1821) enlisted in the British Army's 5th Regiment of Foot. She fought in the Battle of Fontenoy and was wounded in action.
- Anna Maria Lane (1755–1810) dressed as a man to join the Continental Army in 1776 and fight in the American Revolutionary War with her husband until 1781, later received a pension for her courage in The Battle of Germantown.
- Deborah Sampson (1760–1827) of Massachusetts was the first known American woman who disguised herself as a man (“Robert Shurtliff”) to enlist as an infantry soldier. She served in the Continental Army in the Revolutionary War.
- Hannah Snell (1723–1792) was an Englishwoman who entered military service under the name "James Gray", initially for the purpose of searching for her missing husband. She served in General Guise's regiment in the army of the Duke of Northumberland, and then in the marines.
- Ulrika Eleonora Stålhammar (1688–1733) was a Swedish female soldier during the Great Northern War, later put on trial for having served in the military posing as a man.
- Joanna Żubr (1770–1852) was a Polish soldier of the Napoleonic Wars and the first woman to receive the Virtuti Militari, the highest Polish military order.
- Albert Cashier (1843–1915), born Jennie Irene Hodgers, was an Irish-born woman served three years in the Union Army during the American Civil War as a male soldier, and lived the next fifty years as a man.
- Maria Quitéria (1792–1853) was a heroine in the independence of Brazil, when she fought against the Portuguese troops in Bahia. Later, she was awarded by the Emperor Dom Pedro I.
- Jane Dieulafoy (1851–1916) was a French woman who, when her husband enlisted during the Franco-Prussian War, dressed as a man and fought alongside him.
- Nadezhda Durova (1783–1866) was a decorated Russian cavalry soldier of the Napoleonic Wars who spent nine years disguised as a man.
- Eleonore Prochaska (1785–1813) was a German woman soldier who fought in the Lützow Free Corps during the War of the Sixth Coalition.
- Friederike Krüger (1789–1848) was a soldier in the Prussian army.
- James Barry (c. 1792–1795 – 25 July 1865) was a military surgeon in the British Army who is widely believed to have been born female and named Margaret Ann Bulkley.
- Anna Lühring (1796–1866) (sometimes wrongly referred to as Anna Lührmann) was a German soldier in the Lützow Free Corps during the Napoleonic Wars.
- Nathaniel Lyon (1818–1861) General for the Union during the American Civil War, allegedly dressed as a woman to spy on an enemy encampment.
- Giuseppa Bolognara Calcagno (1826–1884) was a heroine in the liberation of Catania in support of Garibaldi's Expedition of the Thousand; she wore only men's clothing, lived like a man among the male soldiers, and was awarded the Silver Medal of Military Valor.
- Frances Clayton (c. 1830 – after 1863) was an American woman who disguised herself as a man to fight for the Union Army in the American Civil War.
- Mária Lebstück (1831–1892) was a Hussar officer during the Hungarian War of Independence of 1848 and 1849 under the name Károly Lebstück.
- Sarah Rosetta Wakeman (1843-1864) served with the Union Army in the American Civil War under the Alias of Lyons Wakeman and Edwin R. Wakeman. Her letters remain one of the few surviving primary accounts of female soldiers in the American Civil War. 
- Sarah Emma Edmonds (1841–1898) served with the Union Army in the American Civil War disguised as a man named Frank Thompson.
- Mollie Bean served with the Confederate Army in the American Civil War under the alias Melvin Bean.
- Mary and Molly Bell, cousins who both served with the Confederate Army in the American Civil War.
- Cathay Williams (1844–1892) was a former slave who became the first recorded African-American woman in the U.S. Army.
- Loreta Janeta Velazquez a.k.a. "Lieutenant Harry Buford" (June 26, 1842 – c. 1897) – A Cuban woman who donned Confederate garb and served as a Confederate officer and spy during the war.
- Rani of Jhansi (1828–1858) fought in the Indian Rebellion of 1857 by dressing as a sowar on behalf of her adopted son. Her identity was revealed when she was slain in battle.
- Viktoria Savs joined the Austrian army during World War I.
- Flora Sandes joined the Serbian army during World War I.
- Wanda Gertz (1896–1958) joined the Polish Legion in World War I to fight on the Eastern Front while posing as "Kazimierz Zuchowicz". Later she joined the Women's Voluntary Legion, and during World War II she commanded an all-woman sabotage unit of the Home Army.
- Dorothy Lawrence (1896–1964) was a British reporter who served as a man in the army during World War I.
- Zoya Smirnow (1897/98 – after 1916) was a Russian schoolgirl who along with 11 other friends ran away from their Moscow school and disguised themselves as men and joined the Russian army where they fought in Galicia and the Carpathians during World War I. After a death and number of injuries in the group, Smirnow's sex was discovered. She recounted their story to the English press.
- Frieda Belinfante (1904–1995) was a prominent musician and World War II Dutch Resistance fighter who disguised herself as a man for 6 months to avoid capture by the Gestapo.
- Henk Jonker (1912–2002) was a member of the Dutch resistance who disguised himself as a woman.
- Ehud Barak (b. 1942), the later prime minister of Israel, disguised himself as a woman to assassinate members of the Palestine Liberation Organization in Beirut during the 1973 covert mission Operation Spring of Youth.
- In J.R.R. Tolkien's fantasy novel The Lord of the Rings, the noblewoman Éowyn fights dressed as a man in the Battle of the Pelennor Fields.
- In All the Queen's Men, a 2001 comedy set during WWII, cross-dressing is a central plot device.
- Terry Pratchett's novel Monstrous Regiment is a satirical look at the phenomenon.
- I Was a Male War Bride is a comedy where the male French officer, played by Cary Grant, must dress like a woman to return as a war bride of his American military wife.
- One of the running gags of the TV series M*A*S*H is Klinger's attempts to get discharged from military service by crossdressing.
- In the Disney film Mulan, which is based on the story of Hua Mulan, Mulan dresses as a male to save her father from being drafted.
- In Tamora Pierce's The Song of the Lioness quartet of books, Alanna of Trebond disguises herself as a boy to train to become a royal knight, a position only given to noble-born boys.
- Genesis Climber Mospeada was perhaps the first anime series to feature a regular crossdresser, Yellow Belmont, amongst the main protagonists.
- H. E. Bates's novel The Triple Echo is about a World War II army deserter who cross-dresses to avoid arrest. This was made into a film in 1972.
- Mary "Jacky" Faber does this as the titular heroine of the Bloody Jack series of novels, fighting in the Napoleonic Wars.
- Leviathan by Scott Westerfeld, a steampunk novel in which Deryn "Dylan" Sharp disguises herself so she can join the Royal Air Service.
- In the manga and subsequent television series The Rose of Versailles, Lady Oscar François de Jarjayes acts as the head of the Versailles royal guards and the personal bodyguard of Princess, later Queen, Marie Antoinette during the years leading up to the French Revolution. What is unique about her cross-dressing is that, while Oscar wears men's clothing full-time and conducts herself as a man, she is open about being female.
- The Shadow Campaigns novel series by Django Wexler has a female main character rise through the ranks of an army while disguised as a man.
- Spector, Peter (2016-03-01). The Wiley Blackwell encyclopedia of gender and sexuality studies. Naples, Nancy A. Malden, MA. ISBN 9781118905388. OCLC 933432480.
- "Achilles among the Daughters of Lycomedes (Getty Museum)". The J. Paul Getty in Los Angeles. Retrieved 2019-03-15.
- 1834-1900., Clayton, Ellen Creathorne (1879). Female Warriors : Memorials of Female Valour and Heroism, from the Mythological Ages to the Present Era. Tinsley Brothers. OCLC 963750555.
- Vaughan, Richard. Philip the Good. pp. 34–49.
- The Wiley Blackwell encyclopedia of gender and sexuality studies. Naples, Nancy A.,, Hoogland, Renée C., 1960-, Wickramasinghe, Maithree,, Wong, Wai-Ching Angela, 1959-. Malden, MA. 2016-05-09. ISBN 9781405196949. OCLC 933386043.CS1 maint: others (link)
- Davies, Christian (1740). The life and adventures of Mrs. Christian Davies, commonly called Mother Ross. London.
- Dall, Wells Healey Caroline Wells Healey; Dall, Caroline (April 2010). The College, the Market, and the Court. Applewood Books. ISBN 9781429043441.
- "Charles Edward Stewart: The Young Pretender". The Scotsman. UK. Retrieved 5 September 2012.
- Wakeman, Sarah Rosetta; Burgess, Lauren Cook (1994). An Uncommon Soldier: The Civil War Letters of Sarah Rosetta Wakeman, alias Pvt. Lyons Wakeman, 153rd Regiment, New York State Volunteers, 1862–1864. The Minerva Center. ISBN 0963489518. OCLC 30933373.
- "Hispanics in the Military". Valerosos.com. Retrieved 2013-10-22.
- "The Hispanic Experience – Contributions to America's Defense". Houstonculture.org. Retrieved 2013-10-22.
- "Kvinnorna som klippte håret, tog på sig manskläder och tog värvning", Studio Ett , Sveriges Radio, 7 October 2016. Retrieved 9 October 2016.
- Hirschfeld, Magnus (1930). The Sexual History Of The World War (revised edition 1946). Cadillac Publishing. Page 100.
- Jones, David E. (2000). Women Warriors: A History. Washington D.C.: Brassey's. p. 134 ISBN 1-57488-206-6
- Salmonson, Jessica Amanda (1991). The Encyclopedia of Amazons. Paragon House. Page 236. ISBN 1-55778-420-5
- Liepman, Ruth (1997). Maybe Luck Isn't Just Chance. Northwestern UP. p. 66. ISBN 9780810112957.
- "Profile: A trusted leader". news.bbc.co.uk. January 27, 2000. Retrieved 2008-06-12.