Ringside Chat: Caroline Grosso



Caroline Grosso’s Instagram feed is a total dream. Heaping plates of spaghetti, an impossibly adorable French bulldog named Louie, and impeccably styled outfits of the day have us double tapping the like button—and screenshotting the senior fashion editor at W’s outfits for future inspiration. 


She’s also an equestrian (something you can see hinted at in her personal style) and recently starting to ride again after a ten year hiatus.

“I was craving a bit of open space, and to be honest, an excuse to put down my phone,” Grosso says. “So after toying with the idea of going back to the sport for months, I decided to go for it. It’s been about a year and a half now that I’ve been back at it, and it’s one of the most rewarding choices I’ve made.”

We chatting all things horses with her—how it’s influenced her personal style, what her best memory from riding is, and how sometimes you have to break fashion rules—below.


What first drew you to riding?

I think it may be my grandparents’ fault. They took me for a pony ride when I was very young, and I think that is where my initial interest started. But my sister and I were very much the girls who begged and begged for a pony, and eventually, my parents gave in. I loved horseback riding for the time spent with the horses as well as the close friendships that I developed with other girls my age at the stable, and getting to know the horse community at large.

How has equestrian style influenced the way you dress?

How has it not! I have a stash of things in my apartment I have collected over the years that feel more horse girl than fashion editor. For a number of years I was very much the New Yorker who dressed in head to toe black. These days I am much more open to other colors (and by color, I really just mean other neutrals—navy, browns, rust, and all shades of cream) and so those equestrian-isms have started to creep back in. It works both ways actually. Working in fashion has completely skewed what I wear to my stable, and for better or worse, I don’t know. Instead of riding in beige breeches, I really like to try out different colors - a chic navy, a burgundy. Once I got the Free x Rein Derby Riding Pant in white the perfect mustardy-brown suede knee patch, I absolutely had to wear it right away. So what if white is meant for the show ring only? I wanted to try it and it looked chic so I just wore it in a lesson anyway.

What's your fondest memory from riding?

Well there was one season in particular when I cleaned up on the show circuit and—full nerd fact—was crowned New Jersey’s Equestrian of the Year. But truly, before all that and before I had my own horse in my backyard, I leased this gorgeous black thoroughbred with a white star, named Jack. And Jack was a pain in the ass. Every time you would go and get him out of the paddock, no matter who you were, he’d pin his ears, charge at full speed, and the next thing you know all 14 horses in his paddock were galloping circles around you because as the alpha, he’d riled them all up. But once, when I had had a particularly bad day, I went to his paddock to grab him for our lesson and he walked right up to me, wrapped his neck around me, and rubbed my back, essentially giving me a hug. To this day I swear he could read my emotions, and the calming effect of being around horses is one of the reasons I picked it up again after a decade-long break.

There are so many designers who find inspiration from equestrian style. What do you think makes it so popular?

I think for an outsider looking in, the sport looks so chic and glamorous—the show outfits, the strong and sleek horses. I also think it’s a never ending source of inspiration in part because many women who are often noted as style icons were also avid equestrians—like Jackie Kennedy and even Mary-Kate Olsen, for example.


How do you like to wear your Free x Reins?

After I ride and get back into the city on a Saturday afternoon, I often have little errands to run or will meet up with friends for a quick coffee, so I always try to look relatively put together. I’ll wear my Free x Rein breeches and throw on a slide or a ballet flat (or if it’s not hot out, I’ll leave my boots on) and go about my day. It’s is so very easy to go from stable to city with these! I personally believe too many equestrian apparel brands have gone too athleisure. And many of the fits and cuts that I see at my local tack shop are quite far behind what stylish women wear in their day to day lives. It is refreshing to see a young label pushing the boundaries of what an equestrian apparel brand can be. Can’t wait to try out the bodysuits next!


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