Lady soldiers in drag

The USNIBlog has a list of notable women who served in the military by pretending to be a man, and the reasons why they did it: out of patriotism, out of desire to explore the world, and sometimes to accompany a husband or lover.

Not in the list: Dr James (Miranda) Barry: who actually attended medical school in the days when women were banned, and then later joined the British Navy and was sent to CapeTown:

In 1822 Somerset appointed Barry as Colonial Medical Inspector,[28] an extraordinary jump in expectations from Barry's low military rank which brought with it great responsibility. Over ten years of work in the Cape, Barry effected significant changes, among them improvements to sanitation and water systems, improved conditions for slaves, prisoners and the mentally ill, and provision of a sanctuary for the leper population...

Wherever Barry served across the British Empire, improvements were made to sanitary conditions and the conditions and diet of both the common soldier and other, under-represented groups. Barry was outraged by unnecessary suffering, and took a heavy-handed and sometimes tactless approach to demanding improvements for the poor and underprivileged which often incited anger from officials and military officers; on several occasions Barry was both arrested and demoted for the extremity of this behaviour.

heh. Trouble maker. The UKMail article about her relates that her bad temper is one reason no one suspected that Barry was a woman.

Dr Barry, left, pictured with her dog Psyche and servant John, right, while in Jamaica in 1862. Alamy stock photo.

Another troublemaker; Catalina de Erauso , aka LieutenantNun (she was a runaway nun)
more here.

she could hold her own in a fight, to say the least, although some suspect the stories in her autobiography were a bit exaggerated.

One reasons she didn't get into trouble with the Inquisition was that she remained a virgin, and later received permission from the Pope to cross dress.

In contrast, Barry might have born a child out of wedlock at a very young age (?sexual abuse) because of the appearance of a young baby in the family, officially the child was her "sister"...but the history is unclear.

A lot of this is about overcoming the limitations on the female role model in those days, not about sexual confusion per se. Some may have been lesbians, others were married, and most probably celibate.

on other famous crossdresser was not in the military, except maybe as a scout: Calamity Jane is famous in frontier history: autobiography here.
again, much of her story might be exaggerated or made up.

Ironically, she had several children, (discussion here).