You might find some useful leads in an essay I wrote on female cross-dressing 
in the SCA's period (and in the SCA). While about half the essay is more on the 
"interactional theater" aspects of women cross-dressing in the SCA, the first 
part is an exploration of the motifs and evidence for cross-dressing women in 
history and literature up through the Renaissance. And there's an extensive 
bibliography for further reading.  The article is here: 
http://www.heatherrosejones.com/gender/scacrossdressing.html

Heather

On Oct 6, 2013, at 6:06 PM, Elizabeth Jones wrote:

> Does anyone have SCA period (i.e. medieval to 1600) images or
> documentation referring to cross dressing. I am in the early stages of
> trying to organise a Bob and Kate feast around this time next year
> (for those unfamiliar with the concept the name comes from the episode
> of Blackadder II episode 'bells' in which a young woman named Kate
> disguises herself as a boy called Bob to become Blackadder's
> manservant http://en.wikipedia.org/wiki/Bells_%28Blackadder%29 so
> obviously it's about cross dressing). It has to be in October as it's
> supposed to be a fundraiser for the Ovarian Cancer foundation's
> 'Frocktober' campaign (www.frocktober.org). A year's lead time means I
> hopefully have enough time to get people OK with, or maybe even
> excited about, the idea of cross dressing my two basic strategies are
> telling people that it's for a good cause and showing them that it's
> period (at least in certain circumstances). The 'it's period' part is
> where I need the help of you lovely people to dig out all of those
> obscure sources you have tucked away.
> 
> Thanks for your help in advance,
> Elizabeth
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