The Renewed Appeal of Riding Aside

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It was the picture that launched a thousand riding lessons.

Lady Mary Crawley astride—or more correctly, aside—a black hunter, gazing from beneath a top hat and veil, her voluminous black apron gracefully swoop-ing toward her mount’s knees. It was, if you will, an Alfred Munnings portrait in pixels.

Women (and the occasional man) have been riding sidesaddle for hundreds of years, but the style began to die out in the 1930s as it became socially acceptable for ladies to be seen riding in breeches. It survived as a hunter-show appointment class (points off if that’s not sherry in your flask) and with English riding instructor Roger Philpot, who taught Downton Abbey’s Michelle Dockery to ride aside, as keeper of the flame. But as Philpot observed in London’s Daily Telegraph, “Downton put riding sidesaddle on the map,” reporting that he received a flurry of calls for lessons after each show.

It was two Englishwomen, Philippa Holland and Lady Martha Sitwell, who promoted the interest in riding aside. Sitwell, a close friend of Holland’s and also a sidesaddle enthusiast, began designing bespoke sidesaddle habits. In 2014, Lady Sitwell, together with her sister Clementine de Blank Chappell and son, Conor de Blank, set off on a month-long sidesaddle trek through Mongolia to benefit Mind, a mental health charity. Today, thanks in part to these two women, there are more side-saddle clinics and women riding aside than ever. And who better to unravel the mysteries of riding aside than Holland and Sitwell.

Arranging a meeting with Holland is complicated by the fact that a call to her cell phone is usually met with “Can’t talk now, I’m on a horse.” On one such occasion, the music of hounds and the huntsman’s horn resounded in the background.

Off a horse, Holland proves to be a 30ish and slender 5 foot 10. The conversation jumps between talk of hunt meets recently ridden, her eponymous line of jewelry, and the London social scene. Holland’s been riding since childhood, she explains, but the interest in riding aside blossomed when she dated a young man whose mother was a sidesaddle instructor based in Normandy. Bitten by the sidesaddle bug, Holland crossed the channel regularly for tuition. She and Sitwell met when both took lessons from Philpot.

Foregoing university, Holland completed a history of jewelry course at Sotheby’s, took a gap year to travel, and ended up buying a variety of gemstones in Jaipur, India. Inspired, she began designing jewelry. Today, her work employs a special process of coating natural objects such as seeds and leaves to create earrings, brooches, and other pieces.

It was four years ago that Holland organized the Dianas of the Chase Cup, a sidesaddle steeplechase race, last run in 1924 across the challenging Quorn hunt country. Sitwell was one of the 14 starters, but admits that she didn’t finish the race. “My horse is not very brave,” she says. However, each rider was awarded a special brooch featuring Artemis, the goddess of the hunt, designed by Holland.

Holland has also organized the first sidesaddle race on the flat at Wincanton Racecourse in Somerset, England, and twice (riding astride) won the Magnolia Cup, a five-furlong race down the homestretch as part of Glorious Goodwood, a five-day festival of horse racing at Sussex downs, England. She hunts twice a week riding aside, and in her one compromise for safety on the hunting field wears a hunt cap, which she calls a dickie, instead of a top hat and veil.

“The hardest part of riding sidesaddle, says Holland, “is getting onto the horse, which is almost impossible without a mounting block or leg up.” The saddle,she explains, has two pommels—one fixed at the top, over which the rider hooks the right leg; and another leaping, at the side, behind which lies the left leg. Once mounted, Holland promises, “You’re really quite secure.” The left leg goes into a single stirrup, and a spur is worn.

What about posting to the trot? “That isn’t a problem,” says Holland.
“A horse properly trained for the sidesaddle doesn’t trot but merely walks or canters, or gallops wildly across the hunt field.” And the problem of signaling for the left canter lead, which in English riding is most often done by dropping the right leg behind the girth? “That’s done with the seat,” says Holland, “but with a well trained sidesaddle horse, you just ‘think about it.’”

But a woman properly seated sidesaddle sits with the poker-straight posture of a lady. In many photos, this results in the rider being left behind and jabbing the horse in the mouth over fences. Holland agrees, and it upsets her. “Too many women just want to be at the meet with top hat, makeup, and a veil, and they don’t take the time to learn,” she says. “You should ride sidesaddle or not at all.”

The kit for sidesaddle differs in many ways from that appropriate for riding astride. The habit does not include skirt as commonly supposed, but rather a voluminous apron with buttons down the back. The rider leaves the apron opewhen riding so it doesn’t get tangled in the pommel when you fall and then buttoned up for modesty when on foot. Underneath the apron, the rider wears breeches that zip on the side. “The breeches should be the same color as the jacket,” adds Sitwell, “so when you fly over fences and the apron whips out and shows your bum, you match.”

“The boot is shorter than a regular riding boot,” comments Holland. “It’s to keep you from tangling in the pommel if you fall,” says Sitwell. “And the whip is long like a dressage whip, but weighted at the end, like a jockey’s bat.”

Sitwell, whose Sitwell and Whippet line of riding habits are sewn in Savile Row in central London, says there are differences in hunting coats. “The jacket on a hunting coat for a member of the hunt traditionally has three buttons,” she elaborates, “while the sidesaddle coat is shorter. Therefore, two buttons, or even one, are appropriate.” The color-matched breeches don’t have Velcro closures at the ankle, but rather old-fashioned buttons and buttonholes.

The name for her bespoke line, says Sitwell, came to her naturally: “You know, sit well on a horse, and my dog is a whippet.” In later Downton Abbey episodes, Lady Mary, played by English actress Michelle Dockery, rode sidesaddle in tweeds and a bowler, and the extras in the scene were recruited from the Dianas of the Chase cast. That gave rise to speculation that it wasn’t Michelle Dockery cantering across the finish line, but a double.

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