Stump & Judy

My handwriting has gotten pretty bad over the years, so I'm not one to criticize, but "Stump & Judy" is a best guess on what's written on the back.

Anyway, to return to a point I've made a few times over the years, in our day and age when a man  wears women's clothing, it's cross dressing, when a woman wears men's clothing it's fashion.  My question has always been;  But what about when this photograph was taken?  The gentleman on the left is a gentleman, but the gentleman the right is a lady.  Could she have walked down the streets of an American city and not been charged with some sort of crime?  How about a more conservative small town?  Would she have been considered scandalous, daring, or both? 

And one more thing which has nothing to do with anything, is it my imagination or does she look a little like a young Diana Rigg wearing John Steed's bowler?