“Rails Happen”: Talking Ponies, Fashion, and Wine with Top Ammie Rider Joey Wölffer

Joey Wölffer is a full-time mom, jewelry designer, boutique clothing entrepreneur—not to mention a top, amateur jumper rider in her own right. She also owns and manages the Wölffer Estate, her family’s Hamptons winery and a sponsor for the Longines Masters of New York.

In honor of #WineWednesdays, PonyApp caught up with Joey to learn more about the faces in her stable, training with Quentin Judge, and why, in horses and in life, sometimes, rails just happen.

Let’s start with a hard one. Tell us about your horses.

JW: I have one horse, Antonov, who I like to call, ‘the King of the Medium Amateurs.’ If I ride well, he can win every class. He’s turning 13 and he’s a Dutch warmblood. [He’s basically] a big, grey unicorn with a fat belly! I also have a new horse who’s name is Sagg Main after the beach where I live [in the Hamptons]. He came over from Germany in January, and I showed him at the end of the [Winter Equestrian Festival]. My goal on him is to do the High Amateur [jumpers].


Joey Wölffer

(c) Kaitlyn Karssen Photography

Have you always been a rider?

JW: When I was six, I started riding, that’s really when we started getting into horses on the farm. My mom got me my first pony when I was 15, but before that, I kind of rode whatever was available. Honestly, it’s made me appreciate later on in life—buying my own horses and learning the value of a nice horse. [But] I feel kind of lucky that I had that early [experience].

I’ve had Antonov since he was six, so I also really like that process of getting to know a horse and learning and growing together. When my dad passed away, I moved out here [to the Hamptons] to take over the business with my brother, and I really ended up getting back into the sport in a different way. Now, it’s like my lifeline out of work. It’s my therapy.


You’re a mom in addition to being a jewelry designer, boutique and winery owner, and a rider. What does work-life balance look like to you and what advice can you give the rest of us?

JW: It’s funny, when my business was small and I was doing everything on my own, it was a stressful time. But I didn’t have kids at that point. I was hungry, and I knew I didn’t want to go back to the corporate world, so I kind of killed myself to start that business. It really set the tone for how I’ve learned to work going forward.

With my kids, if there’s something I really want to do with them mid-week or mid-workday, I plan for that and make that happen. I also have an incredible team of people and, without them, I wouldn’t be able to do anything.

The good thing for me is that because we’re a seasonal business, winters are slower, and that’s my Florida time. I’m actually very focused then on my family and my riding and more on the Florida store. I do make sure I have that winter down time—I couldn’t sustain what I do nine months of the year all year long!

 Joey Wölffer Double H Farm

What’s your proudest career accomplishment?

JW: I’ve not done this on my own—it’s been alongside my husband and my brother and my team—but really, the growth that we’ve accomplished with the winery is incredible, and totally unexpected. We didn’t have anything to compare it to, but we just knew that we wanted to do better than we had done [in the past]. There is this feeling you have for branding, and I just knew, if we stayed true to who we were, and didn’t try to be anyone else, and stayed original, that we would be successful. We all believed in that, and I think that’s what I’m most proud of.

 Joey Wölffer

Okay, let’s talk clothes. How would you define your personal style?

JW: I hate the word Bohemian, but it is Bohemian—sophisticated Bohemian, you know? I used to dress like a bag lady, it was layers and layers upon everything, and I looked enormous, and that was my look. I’ve kind of refined it. Now, it’s a lot of mixed patterns, and I’m not afraid to mix a leopard [print] with a flower or a stripe. But it’s just me. When I’m out here [in the Hamptons], and it’s not summer, I’m in jeans and a sweater. Right now, I’m in riding pants. 


I think, as women, we’ve all had that moment of looking in the mirror and having that feeling of insecurity and asking ourselves, Am I really walking out of the house in this? Do you have any advice for how to handle that moment?

JW: If anything, we’re learning that in this day and age, you’ve got to be who you are in everything you do. If you’re a follower, or you’re insecure, people will walk right over you. You have to be confident in what you’re wearing and what you’re doing. Everybody has a different life and a different [budget], but the nice thing about fashion is, you can kind of buy it at every level. I love [lines like] Zara, and I love vintage. I think it’s about owning who you are, and owning your style, and if that’s what makes you feel good, then that’s what you should wear.

 Joey Wölffer

What piece or pieces are you most excited about in your spring line?

JW: We just started a line of re-worked pieces, because I got tired of looking at old inventory and trying to sell it for nothing. I’m like, These are beautiful fabrics, why can’t we re-use some of them? It’s working, and that makes me really happy, because it’s also sustainable.


You train with Quentin Judge at Double H Farm. What’s the most important lesson he’s taught you in your riding so far?

JW: I think the big thing I’ve learned this year is what happens with your horse outside of riding. My horse goes in the walker every day, and that’s been amazing for his fitness and his colic and ulcer issues. It’s appreciating the importance of what goes on behind the scenes, and Quentin is really open [about that] and that’s something I love.

On a personal level, I’m so competitive, and that’s what has made me successful in work life, but that sometimes gets the better of me in riding. Quentin makes me laugh, and makes me take myself less seriously. [He’s also] such a good teacher, and every time we go in the ring, I have a very specific plan. Maybe it won’t work out, but at least I have a plan!


As a New Yorker, what excites you most about having the Longines Masters of New York in your own backyard?

JW: I’m just so excited that they make riding feel so special. Because I’m an amateur, no one ever watches me, you know? It’s kind of fun that it feels like a spectacle, and I don’t think we get that all the time at shows—it’s like I’m performing. 

It’s also fun that it’s all about the spectators, and the experience, and the food and the wine. [Wölffer] is sponsoring the show, and I love that it’s such an event—that’s something that I’m really looking forward to.


What lessons have you learned from show jumping that can be applied to other areas of your life?

JW: Things rarely ever go exactly as planned. You have to improvise, and your ego is constantly being deflated in riding—and I love that! Someone is always better and there’s someone that’s always more successful and smarter, and that’s just how it goes. That’s the key thing about being a successful business person, [too]. Guess what? You might get a lawsuit, things are going to fly in your face, and the way you deal with it is the way you get out of it. You can’t take it all personally.

One day, I had waited all season to ride my amazing horse in the International Ring [at WEF]. I put so much pressure on it that I literally stopped counting, and he ended up stopping, which he never does. I was devastated, and it was all because I’d had a rail early on, and was so disappointed in myself. But guess what? Rails happen. Mistakes happen, and it’s fine. No one cares. There’s no need to beat yourself up about it.

Joey Wölffer

(c) Kaitlyn Karssen Photography

Last question: as it is #WineWednesday, what’s your favorite way to enjoy a glass of your favorite Wölffer wine?

 JW: It’s with a combination of family and close friends. Our Wine Stand is on Fridays and Saturdays in the summer, and we have tons of families that attend and live music, and we just kind of celebrate with our kids and enjoy the sunset and the summer. That’s what I’m all about. I like how our wine reminds me always of that experience: summer with friends and family. 

Wölffer Estate Rosé
All photos courtesy of Joey Wölffer 

Great article, Wölffer Estate is my favorite spot in the Hamptons!

Wonderful article!! Keep them coming!

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