Somewhat interesting...the WOB is depicted riding sidesaddle in every picture. (Except perhaps #13? hard to tell...) For most of European history it was considered immodest for women to straddle the horse when they rode. Some of the artists probably just reflected the reality of the time without thought to why women rode sidesaddle, some perhaps painted to the sensibilities of their viewers / patrons.
(Slide...) Does any woman in Modern America rides sidesaddle? Dubious. although pretty sure Amish women always use a carriage and not a saddled horse.
Anna Morgan, AQHA | American Quarter Horse Association.