For many centuries, side-saddle was considered the only way for a lady to proceed 'properly' on horseback. The art is depicted in early editions of The Canterbury Tales, while a recent find in the Isle of Man suggests that it was already practised before 1000 AD. Very popular in the 1920's in Britain the emphasis was as much on elegance, style and 'propriety' as on technique, horsemanship and courage. Ladies' grooms rode side-saddle to train and keep their ladies' horses fit.
H.I.M. The Empress of Austria, rode sidesaddle regularly with the Pytchley. She helped set the pace in saddle design, by demanding the same, or indeed greater, durability and security for the side-saddle rider, whether hacking in a London park or keeping up with hounds.
World War II led to shortages of clothing materials, of trained saddlers and other staff, and the emergence of a not-so-affluent society. With a few hard-core exceptions, side-saddles, habits, veils and silk hats remained in the attics where they had lain throughout the War. Many now chose to ride astride. Some could see no further use for them, and destroyed them.
With equestrian sports becoming a growth leisure pastime, riders and spectators alike missed the beauty and elegance which had contributed to the pre-war equestrian scene, in and out of the hunting-field. But rarely was a horse seen ridden side-saddle.

In 1974 Valerie Francis and Janet Macdonald formed the Ladies' Side Saddle Association — now The Side Saddle Association — to regenerate a skill and an art that many wished to preserve and foster. Hundreds of well-preserved side-saddles and habits have now come back out of storage, with many shows having demonstrations of side saddle riding.