A story attributed to Ambroise Paré describes what it considers a spontaneous change of sex of a teenaged woman to a man called Germanus Maria or Germanus Garnierus, which if true is more likely the tale of an intersex boy, initially presumed to be a girl whose testicles descended late upon adolescence.
1551-1589 Culture King Henri III of France is known to have favored wearing women’s clothing at court entertainments. He is also said to have carried on romantic relationships with men but some dispute that as being false political attacks.
Legal A number 17th, 18th, and 19th century examples of trans men or gender nonconformity involve “female husbands”, a person who was assigned female at birth, lived as a man, and married a cisgender woman. It is usually unclear if such a person was a trans man or if they were a cisgender lesbian, crossdressing in order to maintain a relationship within the social structure of the time. Records of these relationships most often exist due to court records of such husbands being tried for fraud.
1600s:Legal In Spain crossdressing was illegal, except during Carnivale
1584-1659 Culture Mary Firth/Moll Cutpurse was an English thief and criminal who crossdressed as a man, performing bawdy songs while doing so creating a distracting personality while she accomplished her thievery.
1620: Culture In Lisbon, Portugal "danças dos fanchonos" were held - which were essentially drag shows and parties
1626 - 1689 Culture Queen Kristina of Sweden may have been intersex or trans and/or lesbian but was decidedly gender non-conforming. Various descriptions of her birth and youth comment on her being mistakenly identified as a boy at birth and rejected for masculine features by her mother. There were times when she adopted a more masculine form of her name, Kristine Alexandre, and presented herself in male garb. There’s also indications she had some attraction to women and ambivalence towards men.
1644 - 1724 Culture François-Timoléon de Choisy/Madame de Sancy/Comtesse des Barres was a member of the French nobility, an abbé and an author. As a child, with the direction or support of his mother, he dressed as a girl. Upon turning eighteen, he attended the Sorbonne wearing men’s clothing but after completing his studies there he mainly wore women’s clothing. He became an abbé and in 1695, in some manner of collaboration with Marie-Jeanne L'Héritier and Charles Perrault wrote The Story of the Marquise-Marquis de Banneville a tale of a marquise who was a boy raised as a girl, and a marquis, who was a girl passing herself off as a boy, who fall in love and get married. Most writings describe de Choisy as a transvestite or crossdresser, but she may have been a trans woman.
1650s: Culture Clandestine parties for gay men and crossdressers are held in Mexico. Their participants are prosecuted.
1700s - 1800s:Culture Molly Houses in England were places where gay (or bi) men gathered to socialize, throw parties, and otherwise hang out. A number of these members wore women’s apparel and adopted women’s names while in attendance. Those doing so appear to mostly have been cis gay male crossdressers rather than trans women. A number were raided and members were convicted of sodomy.
1720 Legal John Ketson, married Ann Hutchinson (Ann Hutchingson), and having been found to have been born under the name Mary, was convicted of fraud.
1721-c.1746 Legal Charles Hamilton was either a trans man or lesbian crossdresser with the birth name “Mary”. At age 14 she used her brother's clothes to pose as a boy and apprenticed, in succession, to two different “quack doctors” before establishing her own practice. In 1746, he married Mary Price, who reported that the relationship had been consummated, but after two months accused Hamilton of fraud. Hamilton was imprisoned for 6 months and publicly whipped in multiple neighboring towns, at which point her history is lost.
https://en.wikipedia.org/wiki/Mary_Hamilton_(transvestite)
1728-1810 Culture Chevalier D’Eon The Chevaliere Lia D’Eon de Beumont is perhaps the most well known trans person from before the 20th century. She is well documented elsewhere and search engines can easily point you to more information. She served as a spy for France and Britain, assigned male at birth in France, she lived most of her adulthood in England, accepted as a woman. For a time, a pathologized condition of transvestism was called “eonism” after her.
1745-1779 Culture Casimir Pulaski, was born in Poland, became a soldier and fought on the side of the colonies during the American Revolutionary War. Examination of his remains suggest that he was likely intersex.
1759 Legal Mary Parlour was pressured by her neighbors into having her husband Sarah Paul/Samuel Bundy arrested for defrauding her into marriage and theft of her money and clothes. Mary did not show up to act as a witness at the London trial and Paul/Bundy was released but their male clothes were burned.
1776 Culture Public Universal Friend, of Rhode Island, declared their female birthself to have died following an illness and from then forward dressed in men’s or androgynous clothing and considered themselves (without using the label) agender. Raised as a Quaker, they became a preacher of a similar but different sect.
1796 Culture: Friedrich Schiller described gay men as Urning (Uranian in some English translations), a term which came to encompass transgender women as well.