27 Female to male cross dressers

Agnodice or Agnodike is a legendary figure credited as the first female midwife or physician in ancient Athens. Her story is told by the Roman author Gaius Julius Hyginus in his Fabulae. Agnodice is not generally believed to be a historical figure, but her story has been frequently deployed as a precedent for women practising midwifery or medicine, or as an argument against either of these.

Jeanne Baret was a member of Louis Antoine de Bougainville's colonial expedition on the ships La Boudeuse and Étoile in 1766–1769. Baret is recognized as the first woman to have completed a voyage of circumnavigation of the globe, which she did via maritime.

Elizabeth Williams Berry, who became known as Mother Berry some time after 1900, was an Australian-born jockey who rode in multiple nations disguised as a man, using the name Jack Williams. After moving to the United States about 1900, she married, and gained the nickname "Mother" after being granted custody of a runaway boy. She retired from jockeying to become a horse trainer. Berry and her husband settled in Helena, Montana, where, at age 111, she was declared the oldest person in Montana at the time. She lived to see women ride as licensed jockeys in 1969 and died at age 114.

Amy Maud Bock was a Tasmanian-born New Zealand female confidence trickster and male impersonator, whose trials and cross-dressing interlude have made her a subject of perennial historical interest in her adopted country.

Anne Bonny was an Irish pirate operating in the Caribbean, and one of the most famous female pirates of all time. The little that is known of her life comes largely from Captain Charles Johnson's A General History of the Pyrates.

Charlotte Charke was an English actress, playwright, novelist, autobiographer, and noted transvestite. She acted on the stage from the age of 17, mainly in breeches roles, and took to wearing male clothing off the stage. She assumed the name "Charles Brown" and called her daughter "Mrs. Brown." She suffered a series of failures in her business affairs after working in a variety of trades commonly associated with men, from valet, to sausage maker, farmer, pastry chef, and tavern owner, but finally achieved success under her own name as a writer, ending her life as a novelist and memoirist.

Lillie (Elizabeth) Hitchcock Coit was a patroness of San Francisco's volunteer firefighters and the benefactor for the construction of the Coit Tower in San Francisco.

Ellen Craft (1826–1891) and William Craft were American fugitives who were born and enslaved in Macon, Georgia. They escaped to the North in December 1848 by traveling by train and steamboat, arriving in Philadelphia on Christmas Day. Ellen crossed the boundaries of race, class, gender, and physical ability by passing as a white male planter with William posing as her personal servant. Their daring escape was widely publicized, making them among the most famous of fugitives from slavery. Abolitionists featured them in public lectures to gain support in the struggle to end the institution.

Isabelle Wilhelmine Marie Eberhardt was a Swiss explorer and author. As a teenager, Eberhardt, educated in Switzerland by her father, published short stories under a male pseudonym. She became interested in North Africa, and was considered a proficient writer on the subject despite learning about the region only through correspondence. After an invitation from photographer Louis David, Eberhardt moved to Algeria in May 1897. She dressed as a man and converted to Islam, eventually adopting the name Si Mahmoud Saadi. Eberhardt's unorthodox behaviour made her an outcast among European settlers in Algeria and the French administration.

Saint Euphrosyne of Alexandria, also called Euphrosynē, was a saint who disguised herself as a male to enter a monastery and live, for 38 years, as an ascetic. Her feast day is celebrated on September 25 by the Greek Orthodox Church and January 16 by the Roman Catholic Church. Euphrosyne was born to a wealthy family in Alexandria; her father Paphnutius was a devout Christian and her mother died when Euphrosyne was twelve. When she was 18, her father wanted her to marry, so she escaped, disguised as a man, and entered the same monastery he often visited for spiritual counsel. She spent most of her years as a monk in seclusion because her beauty tempted the other monks. During the final year of her life, Euphrosyne became her father's spiritual director, comforting his grief over losing his only daughter. Eventually, she revealed her identity to him and they reconciled. After she died, he entered her monastery and became an ascetic himself, living in her cell until he died ten years later. There has been discussion about how Euphrosyne's story fits into issues of homosexuality, gender identity, and gender reversal in same-sex communities in monastic times.

Mary Hamilton was the subject of a notorious 18th-century case of fraud and female cross-dressing, in which Hamilton, under the name of Charles, duped a woman into a supposed marriage.

Yoshiko Kawashima was a Qing dynasty princess of Manchu descent. She was raised in Japan and served as a spy for the Japanese Kwantung Army and Manchukuo during the Second Sino-Japanese War. She is sometimes known in fiction under the pseudonym "Eastern Mata Hari". After the war, she was captured, tried, and executed as a traitor by the Nationalist government of the Republic of China. She was also a notable descendant of Hooge, eldest son of Hong Taiji.

Margaret King (1773–1835), also known as Lady Mount Cashell and Mrs Mason, was an Irish hostess, writer, traveller, and medical adviser. Despite her wealthy aristocratic background, she had republican sympathies, shaped in part by having been a favoured pupil of Mary Wollstonecraft. In Italy in later life, she reciprocated her governess's care by offering maternal aid and advice to Wollstonecraft's daughter Mary Shelley and her travelling companions, husband Percy Bysshe Shelley and stepsister Claire Clairmont.

Marina, distinguished as Marina the Monk and also known as Marinos, Pelagia and Mary of Alexandria, was a Christian saint from part of Asian Byzantium, variously said to be Syria or Lebanon. Details of the saint's life vary.

Mathilde de Morny was a French aristocrat and artist. Morny was also known by the nickname "Missy" or by the artistic pseudonym "Yssim", or as "Max", "Uncle Max", or "Monsieur le Marquis". Active as a sculptor and painter, Morny studied under Comte Saint-Cène and the sculptor Édouard-Gustave-Louis Millet de Marcilly.

Pelagia, distinguished as Pelagia of Antioch, Pelagia the Penitent, and Pelagia the Harlot, was a Christian saint and hermit in the 4th or 5th century. Her feast day was celebrated on 8 October, originally in common with Saints Pelagia the Virgin and Pelagia of Tarsus. Pelagia died as a result of extreme asceticism, which had emaciated her to the point she could no longer be recognized. According to Orthodox tradition, she was buried in her cell. Upon the discovery that the renowned monk had been a woman, the holy fathers tried to keep it a secret, but the gossip spread and her relics drew pilgrims from as far off as Jericho and the Jordan valley.

Zelma Rawlston was an American singer, comedian, and vaudeville performer, specializing in male impersonation, born Zelma Stuchenholz in Germany. She was billed as the "American Vesta Tilley."

Mary Read, also known as Mark Read, was an English pirate. She and Anne Bonny are two of the most famed female pirates of all time, and among the few women known to have been convicted of piracy during the early 18th century, at the height of the "Golden Age of Piracy".

Mary Reibey née Haydock was an English-born merchant, shipowner and trader who was transported to Australia as convict. After gaining her freedom, she was viewed by her contemporaries as a community role model and became legendary as a successful businesswoman in the colony.

Victoria Mary Sackville-West, Lady Nicolson, CH, usually known as Vita Sackville-West, was an English author and garden designer.

Theodora of Alexandria was a saint and Desert Mother who was married to a prefect of Egypt. In order to perform penance for a sin she committed, she disguised herself as a man and joined a monastery in Thebaid. Her true identity as a woman was discovered only after her death.

Anne Jane Thornton (1817–1877), also spelt Ann Jane Thornton, was a 19th-century adventurer from Donegal who in 1832 posed as a boy to go to sea, in pursuit of a lost lover who had gone to the United States. She continued her career as a seaman until her arrival in London in 1835, when she was interviewed by the Lord Mayor of London. She later wrote a book about her adventures.

Isabel Vargas Lizano, better known as Chavela Vargas, was a Costa Rica-born Mexican singer. She was especially known for her rendition of Mexican rancheras, but she is also recognized for her contribution to other genres of popular Latin American music. She was an influential interpreter in the Americas and Europe, muse to figures such as Pedro Almodóvar, hailed for her haunting performances, and called "la voz áspera de la ternura", 'the rough voice of tenderness'. The Latin Academy of Recording Arts & Sciences, presented her with a Latin Grammy in 2007.

Catterina Vizzani, alias Giovanni Bordoni (1719–1743), was an Italian woman who became famous after her death for living life as man.

Dr. Hjelmar von Danneville (1860-1930) was a prisoner in New Zealand suspected of being an imposter during World War I due to her gender non-conformity.

Lena Waithe is an American screenwriter, producer, and actress. She starred in the Netflix comedy-drama series Master of None (2015–2017). She became the first black woman to win the Primetime Emmy Award for Outstanding Writing for a Comedy Series in 2017 for writing the show's "Thanksgiving" episode, which was loosely based on her personal experience of coming out to her mother.

Paula (Paola) Rosa Wiesinger was a pioneering Italian alpine skier and mountain climber.