We’ve all had those moments when either a horse—or a rider—really catches our eye. And sometimes, on special occasions, they both do. This happened to me recently, when I found myself a spectator at a U/25 Division event. A beautiful bay and a poised young rider were in the International Ring at WEF, and it looked effortless (an impressive feat, considering how competitive the U/25 division is, and how talented the next generation of top show jumpers are). They were a delightful pair to watch, and it was the kind of trip around the ring that makes you smile, full of grace and dynamism. The horse clearly enjoyed what he was doing, and the rider was largely to thank for it. Intrigued, I stopped to watch the rest of the course—a lovely clear. It turns out the jockey was Caitlyn Connors.
While it was my first time watching her in person, I was no stranger to her name. Caitlyn has been quietly collecting top accolades in the U/25 division, where she’s also been turning heads with her signature stylish aesthetic.
Since witnessing her trip around the ring that stopped me where I stood, I’ve been lucky enough to have a few conversations with Caitlyn. And I’ve learned that this elegant young rider is one to watch both inside and outside the arena. It turns out her noticeable sense of style is not just a function of her keen eye for fashion. It’s due to her keen eye for business, as well. Caitlyn proudly sits in her bespoke Hermes saddle and wears her tailored Hermes jackets for a reason. While Caitlyn has been developing young horses with her trainer—international grand prix rider Roberto Teran—she has also established the partnership of her dreams with global fashion leader, Hermes, and this partnership is expanding beyond the show ring.
HD: Caitlyn, you are a young professional in an increasingly challenging sport while juggling your courses at University of Miami. What does your current day-in-the-life look like? What about an ideal day?
CC: Currently my typical day is quite hectic. I wake up, ride my three horses, do homework, go to school for a few hours and come home later that night after classes. It’s the same if I am showing. I wake up, show, then go to school. A dream day for me would be waking up, riding my horses, coming back to my house, going on my computer, and checking my messages to see if there are any emails containing fashion content for me to go over.
HD: As I told you on the phone, your poise in these hectic days and schedules is remarkable. I think it must serve you well in the ring. Has your management of your busy schedule helped you in the ring? Does it translate into your daily life? For example, I have found that my experience as a young professional and college student has helped me manage being a new mom. It’s helped me in the workplace. Have you had any experience like that?
CC: I for sure think that learning to deal with my busy schedule has helped me to deal with the pressure in the ring, and my outside life as well.
I’m a big believer in all things in life relating to one another and helping us with the big picture. Maybe school doesn’t directly relate to my riding, but the lessons I’m being taught—of having to balance travel, riding, and school—has helped me deal with the pressure of having to compete while also having a big class to worry about. It all comes together somehow.
HD: Did you have any Devon Horse Show experience growing up? If so, what was your fondest memory?
CC: Devon Horse Show has been a huge part of my life growing up. For two weeks out of the year, I lived at the show grounds. I would wake up, go to the show, and I would not leave until the last class was over. I live not far from the show, so a lot of my school friends and family would come watch the horses or walk around the fair which was exciting for me. I loved that people I knew from the “normal world” were able to see what the horse world was like. I started showing at Devon when I was young. I did the family class and the pony jumpers when I was around 10-12 years old. Winning the Style Award in the pony jumper division in 2012 was a huge accomplishment for me, but my fondest memory was finishing top 3 in the High Junior Jumper Classic under the lights with my long-time partner Bink-A.
HD: Favorite thing about or to do at Devon?
CC: Devon is like no other show in the country. It isn’t just riding people. People from the surrounding community come to watch too, and everyone in the crowd is jumping your round with you. If you have a rail, you will know because everyone at the show grounds says “Aw” and gets emotional with you. Of course, I also love walking around the show seeing the shops and eating the food. There is something for everyone to do.
HD: You are sponsored by Hermes and going to work for them come summer— a dream partnership! How did this come to fruition?
CC: I am blessed to be able to work with a company such as Hermes. It has been a dream of mine since I first started riding in their saddles when I was 12 years old. A trainer I worked with previously was partnered with Hermes, so I always rode in her saddles and eventually I started wearing their jackets. Everything in their equestrian line is so beautiful it was hard not to fall in love with their products. Their pieces truly belong in a museum. I was very lucky that one of their employees was someone I had known since I was competing in lead line. He knew how hard I worked and how dedicated I was to the sport, so he really supported me and got me the opportunity to work with them. I have been working with them ever since!
HD: Do you have advice for young riders aspiring to turn professional and acquire sponsorships and/or partnerships?
CC: This sport is so difficult at times because of the uncertainty of each day. The best advice I have is to keep pushing. Be dedicated to your work and stay patient. If you use a product and you love it, reach out to the company and see if there is any way you can work together. Show them that you are representing their brand and would love to work with them further.
Young professionals balancing riding and demanding collegiate careers strike a chord with me—I’ve been in her shoes (and her boots). But my fondness for her isn’t just because of the personal parallel. She stands for something, too. And as I talked with her about the fellowship and charm of the upcoming Devon Horse Show, I realized what it is. Caitlyn embodies the fusion of local community-based warmth with ambitious global reach which is what the equestrian industry is, at its best.
A local gal who once did leadline next door at the Devon Horse Show, Caitlyn is now a professional, her business partner is international superstar Roberto Teran, and her next big step for the future is with none other than the globally renowned design house, Hermes. She’s excited to see what the future holds, and rightfully so. I am, too. I’ll be eagerly following her journey and cheering her on along the way.