In 1642, at the beginning of the English Civil War, the Irish Royalist Daniel O'Neill escaped from the Tower of London where he had been imprisoned by the Parliamentarians by

tying bed sheets and a tablecloth together and dressing as a woman

Also, according to the ballad Gude Wallace, William Wallace evaded capture by dressing as a woman. Probably more historically reliable is the case of Bonnie Prince Charlie who avoided capture disguised as Flora McDonald's maid in 1746. Then there is the case of Catalina de Erauso, a Spanish woman who escaped from a convent dressed as a man in 1600.

None of these qualify, though, as all are either post medieval and / or not escapes from captivity (although one might argue a case about escaping from a convent).

Are there any documented cases of anyone in Ancient or Medieval times successfully escaping from captivity by cross-dressing?

By 'escape from captivity', I am specifically excluding cases of avoiding capture. I'm only interested in cases where someone was already being held captive, preferably in a prison or cell.

  • 3
    I assume that Achilles' failed attempt to escape going to the Trojan War doesn't fit rhe bill.
    – Spencer
    Nov 19, 2018 at 18:51
  • 2
    @Spencer Not really, but worth a mention in a comment at least. Nov 19, 2018 at 22:59

1 Answer 1


Alice Tankerfelde (also known as 'Alice Wolfe') is known to have escaped from the Tower of London in 1543 while 'apparelled like a man'.

She had been tried by the Admiralty Court having been charged with two murders (since the murders occurred on water, the Admiralty Court had jurisdiction). Once found guilty, she was sentenced to hang on the pirates’ gallows at Wapping Old Stairs.

She was re-captured after her successful escape from the Tower following an encounter with the City watch. They 'became suspicious' of a woman dressed as a man (‘a oman aparylyd lyck a man’), and took her (together with her accomplice, John Bawde) into custody.

(See case 15 in Early, Erotic and Alien: Women Dressed as Men in Late Medieval London by J.M. Bennett and S McSheffrey; State Papers, National Archives reference SP 3/3, fols. 133-134)

She was subsequently returned to the Tower, and was eventually hanged together with her accomplice.

As an aside, another well-documented example of a cross-dressing escape from the Tower of London, although in this case a post-Medieval one, is that of William Maxwell, 5th Earl of Nithsdale, who was sentenced to death for his role in the 1715 Jacobite rising.

According to the contemporary account, his wife, Lady Nithsdale, visited his cell, accompanied by two acquaintances called Mrs Mills and Mrs Morgan (not her maid, as stated in the Wikipedia article). They dressed Nithsdale up in women's clothes, and an 'artificial headdress', then caked his face in so much make-up that it hid his beard.

Dressed like this, Nithsdale was able to simply walk out of the Tower, holding a handkerchief to his face, after which he fled to Rome.

  • 1
    Thanks for this. I'm a little surprised there isn't anything earlier given how many literary references there seem to be to cross-dressing, especially women 'escaping' arranged marriages. Nov 30, 2018 at 6:56
  • 1
    @LarsBosteen Yes. There is also no shortage of stories about King John escaping various situations disguised as a woman, although none mention that he was held captive IIRC, so not worth mentioning in the answer. In any event, they're probably later calumnies anyway Nov 30, 2018 at 11:21

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