A man in drag would be wearing a dress.
I'm assuming Walsingham is suggesting that one of the women got the position because of her good-looks, but I can't tell which one he defines as better looking. One's tall, busty with brown hair while the other one is short, slender and blonde.
Of the two, I'd say that the brunette is the better candidate, but that's because people usually evaluate tall women as being more intelligent and capable than short ones and her hair style strikes me as more business like. Shorter hair = more masculine and therefore skilled. Long, curl hair = more feminine and frivolous.
The taller one also has a more assertive pose, but it