Deborah the Judge.  Deborah can be found in the book of Judges, she is a judge appointed by God and the Israelites to help settle matters of disagreements of all sorts.  She was know for being wise, kind and compassionate but also her most notable contribution was being a leader and not just a leader but a military leader, one might say a general.  Deborah led an army to defeat the Cannanites that were planning an invasion of sorts.

So what make this story so significant or it should be significant.  Well, for one, Deborah was the only female judge whish was very unusal of the time since the society itself was a patriarchal society and the fact that the men respected Deborah decisions as a judge.  Secondly, A military general came to Deborah and asked that she lead the armies to defende the city-state.  Again a role for men only but here was this woman of some note leading, but there is just one small problem with this story.  Deborah probably put on some sort of body armor and carried a sword or pike (long spear with a steel point for piercing) or other weapon of war.  But doesn't Deuteronomy 22:5 say that women should not wear the garments of men?  And wouldn't that include girging up for war?  Yes to both questions.  But, it would not be a violation of Hebrew law since there is some reabbinical debate over a woman taking up arms in the line of self defense but Deborah's actions step outside of those lines so one would have to go back and re-examine Deuteronomy 22:5 on the grounds that Deborah, a chosen leader by God, would dress in armor, take up a weapon and go to war.  

Circling back to a few ideas of Deut. 22:5.  Establishing is it not about forbbing cross-dressing in terms of gender expression but more about licencious and lisivous behaviors given to pagan rituals and idolatry.  The forbibbing of either gender disguising themselves to enter spaces reserved only for men or only for women and using that disguise as a deciption to engage illicit carnal acts.  That is to say if a man dresses a woman and enters a womans only space just so he can find a woman to have sex or perhaps a women disguised as a man only to have sex with a man or the other theories are that men would cross-dress to decive other men into having a homosexual encounter or the same with the women.  And finally the idea of avoiding conscription into service.  

When you read the story of Deborah and try to make sense of how does that not conflict with the laws laid out in Deuteronomy because it seems to that very thing, its the seen versus the unseen.  The understanding of cultural norms of the time period.  

One other idea on cultural norms, the Scottish.  The men wear Kilts, although less common now and use more for ceremonial than everyday dress, but they an everyday norm in the Scottish highlands as it was very cold, so what separates a kilt from a skirt other than names?  Because the Scottish women wore kilts as well...food for thought.

Deborah the Judge should be looked as a stroung woman who was a leader that was wise and honorable.