For women, sitting aside on a horse dates back to antiquity. For the main part, men rode horses; women were merely passengers, sitting behind the men, either holding the man around the waist or sitting on a small padded seat or pillion. This was partly due to their long, heavy skirts; it was impractical to ride astride. Also riding side-saddle was seen to preserve the ladies’ modesty.
The idea of it being indecent for a lady to ride astride can be traced back to 1382, when Princess Anne of Bohemia rode side-saddle across Europe on her way to marry King Richard II. Riding side-saddle was seen as a way to protect her virginity. Soon it was considered vulgar for any woman to ride astride.
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