PONY MOMS

You won’t find "Pony Mom" in the dictionary or even on Google. But you’ll find them in Wellington, Tryon, Ocala, and Devon. These are the 40-something fashion set—once riders themselves, now living their dreams of ribbons and finals vicariously through their 8–10-year-old daughters. Stand back.

The equestrian world of show jumping can bring fierce competition and money-fueled power grabs to the ring, but it all begins with the kids: adorable and under twelve (mostly girls) in breeches, boots, and bows, navigating courses to impress a salty, sunburned judge—and maybe earn the $3.00 blue ribbon to hang proudly on their bedroom wall. Hugs from mom are optional, photos a must.

Each year, beginning in late December, young riders saddle up ponies (leasing at $30,000/year or buying upwards of $50,000) and train up to five days a week, parading around the showgrounds in search of acceptance. They travel sometimes thousands of miles to earn points, leading to the crown jewel: Pony Finals in Lexington, KY. ...but that’s not the real story.

The children don 3-button blue jackets, oversized helmets, and tightly braided double ponytails, adorned with bows that usually match their Hermès belts (yes, Hermès). The word "cute" gets thrown around as frequently as the manure in the stalls.

But behind the scenes, it’s the Pony Moms stealing the show. Many are divorced, bankrolled either by hefty child support or "family money" (emphasis on the latter). Whether chauffeured by nannies or self-delivered after pilates and tennis (or before their own continuing education in the saddle) the moms make trophy entrances at the Sunday shows for photo ops with their blue-ribbon-winning kids. Hopefully.

Hailing from Park Avenue co-ops, Greenwich estates, Ocala farms, and of course, Palm Beach, they form cliques at the barns (friendly, but not too friendly), cheer for their children's stablemates (while subtly undermining rival moms), and stand where all can see.

Pony Moms will bleed money for their children's success—because thirty years ago, they were striving for the same thing. They know the game. Some antics? Faking illnesses for sympathy, jockeying for extra trainer time, screaming at underpaid grooms, and, yes, the occasional Palm Beach affair (this sport does cost a lot and so does Mom’s outfit). Meanwhile, their children form the pure, unbreakable bonds of friendship—bonds often overshadowed by their mothers’ ambitions.

Jumping over ground poles, cross rails and fences isn’t just a hobby, it's an insanely expensive trajectory. These aren’t ballet lessons, Aspen half-day privates, or even an elite sleepaway camp—multiply those costs by twenty, and you might start to compete nationally.

One Pony Mom was reportedly floored when she saw the farrier’s bill for Daisy’s new shoes: "What?!" she cried. "That’s a good pair of Manolo’s from The Real Real!"

While Grand Prix jumpers compete for $500,000 purses, the children’s rings have the real drama. Most 8–10-year-olds are homeschooled or tutored at picnic tables outside the barns. COVID only accelerated the trend, with virtual learning freeing up even more saddle time—and racking up even more expenses. To check progress, Dad might fly in from Teterboro on the family Gulfstream or NetJets share for the weekend, kiss the blue-ribbon winner, and head back Sunday night.

Through clenched, snowy-white teeth and behind newly acquired implants, Pony Moms congratulate their kids' stablemates while privately chastising trainers for perceived slights in the flat class—where one bad score can erase a perfect round over the fences.

Growing up lower middle class outside Boston, Jody never had anything fancy. Her own mother had remarried a wealthy State Street lawyer, but Jody’s upbringing remained modest.

Her daughter, Saleena, took her first pony ride at the Topsfield Fair at seven years old, with Grandma by her side. Grandma thought it was “so cute” and quickly enrolled her in Saturday lessons. But Saleena wasn’t just cute—she was good. Really good.

Soon, Jody approached her husband—not to ask, but to tell him: their daughter needed a pony. Rather than lease one for $25,000/year, she wanted to buy one for $55,000. He refused—not just because he was highly allergic to horses (true), but because $55,000 was a significant chunk of the family’s income. So, Jody went to Grandma. Grandma wrote the check without blinking, and Saleena’s riding career took off.

Using newly acquired alimony from her second (and just ended) marriage, Grandma happily paid the $5,000 monthly barn and training bills. Now, Florida was calling. In August, Jody, Saleena, her sister, the pony, and the family dog moved to Sarasota—horse trailer in tow. Jody’s husband stayed back in Boston, "trying to sell the house" while managing his five small convenience stores. In Florida, Jody and Grandma quickly found a new trainer—but when friction arose, they pulled Saleena out overnight and moved her across town. It turned out they’d left unpaid debts at the old barns in Massachusetts too—$30,000 each.

Florida life suited Jody. Soon she was getting Botox, updating her wardrobe, and consulting plastic surgeons for a little lift (both breasts and face) Grandma paid, of course.

At barn #3, late payments caught up with them again, so they drove across the state to Wellington. After all, Wellington is where it counts. There, they secured a meeting with Mark Charles—the best children’s hunter/jumper trainer around. He didn’t need new students, he’d been doing this for decades, but after seeing Saleena ride, he offered her a spot.

Jody never mentioned they lived four hours away. What was important was Seleena’s success. For six months, they drove from Sarasota to Wellington and back—four hours each way—for 90-minute lessons, four to six days a week. Monthly barn bills (feed, boarding, tack, farrier, vet, trainer and grooms) averaged $7,000. Eventually, Mark Charles heard about previously unpaid debts (the horse world is tight) and gave them an ultimatum: settle $60,000 in back payments to fellow trainers or leave. Grandma wrote the check. They relocated permanently to Wellington. Jody celebrated with a full cosmetic overhaul.

Mary was from the UK: fit, fifty, and full of British vigor. She had married a Caribbean banker twenty-five years her senior—wherever the money came from, she didn’t ask. Their daughter, Milly, at eleven, was a rising star. Riding was her escape from a chaotic home life.

Mary was the quintessential Pony Mom: 5'7", flowing red hair, over tanned, enormous enhanced breasts, sleek white breeches, a tight H buckle affixed to her waist, custom Romitelli boots, Chanel sunglasses, $75,000 worth of Van Cleef, Cartier, Tiffany stacked on one wrist, gold Rolex Daytona on the other, and a casual Birkin bag slung over her elbow. Strangely, no wedding ring. No one dare ask.

She stayed just long enough to watch Milly’s warm-up—then it was off to her own barn for a "dressage lesson" with Emilio, the devastatingly handsome Brazilian trainer. Of course. The other moms always found it odd that Milly’s dad never appeared or that Mary always looked like she had stepped out of a Ralph ad. But around the rings at Pony Island, this was normal.

Sometimes, the expenses you see in front of you can double. In Sandra’s case, they did. Divorced from her dentist husband of twenty years, she had two children on saddle. Outfitting her six-year-old daughter and eight-year-old son was enormously expensive, but it paled in comparison to her own ambitions as an Arabian show rider.

Sandra eschewed puffed-up lips, designer clothes, coiffed extensions and over-the-top accessories in favor of frumpy tiered skirts and Birkenstocks. Her real outfits were saved for the show ring: ruffled shirts, accentuated jackets, oversized lace trimmed hats and rhinestone bridles for her $150,000 mount. Sandra would sashay her way to the kids' ring to cheer on her brood, peeking over her Walgreens sunglasses at the other Pony Moms. Sandra was Breckenridge, the others, Aspen/Vail. A-hum.

It never ends—the constant positioning and the wannabes. Some children even enter two horses in cross-rail competitions on Sundays, doubling their chance, and their expenses, at a ribbon. But don’t worry—Grandma will pay for it and Mom will look great.



Lilly Bates is a former Pony Mom. She has seen it all. She stopped riding 15 years ago and is now a grandmother. That could be trouble.