While this year’s lucky snowbirds prepare to fly the coop, those who stand their ground and do battle with Old Man Winter are beginning to get organized as well.  At OR headquarters in New York, the hayloft has been filled to the rafters, the John Deere has received its dose of Diesel 9-1-1 (we learned that one the hard way), and the quarter sheets have been hung in the tackroom with care.

Now, with the barn and horses fully prepped for chilly weather, the time has come to think about tactical gear for winter riding. In New York, this means layers of down, windproof outerwear, scarves, and glove warmers, but even in more temperate climates (like Aiken, South Carolina, where half of Team OR spends each winter), a few warm pieces are a necessity. Even the Florida-bound shouldn’t count their chickens, as we seem to recall a few near-freezing days in Wellington last year.

So…what to wear when one wants to stay warm and look good doing it? Ask and ye shall receive.

Redingote Equestrian Jumper – $278

If you haven’t heard of Redingote Equestrian, you can thank us later. Right now, behold the new brand’s one-piece jumper designed to be worn over riding gear (boots and all!). Slip into this cozy, fleece lined suit between rides, while grooming, or standing ringside. It’s insulated and waterproof, with pockets specifically dedicated to things like treats, spurs, and even a crop. It was designed by an actual horse trainer, so it functions as promised.

Ruespari Surcingle Belt – $75

For us, this is a game changer. Gone are the days of wide, stiff leather belts refusing to mold to the contours of the waist, and cursing the absence of a hole in exactly the right place. Thanks to Ruespari’s line, we no longer have to deal with gaping, pinching, or bulky buckles protruding from beneath our show coats.

Dreamers & Schemers Boobie Boot Socks – $18

These all-weather boot socks are a fall staple at OR. Why? Because they’re functional, comfortable, and five dollars from the purchase of each pair is used to fund breast cancer research, which is a cause that is near and dear to our hearts. Breast Cancer Awareness month may be over, but the battle is not, and we can’t afford notto wear these boot socks daily!

Equiline Magdalena Breech in Tobacco – $279

Colors of breeches this season: Bordeaux, bloodstone, wine, cherry, chocolate. Seems like rust could be on the horizon, doesn’t it? We’re still holding our breath, but in the meantime, we are seriously coveting this tobacco hued pair by Equiline.

MaKeBe Lucy Bomber – $275

We love bombers for their versatility. Over a t-shirt on a warm autumn day, or paired with a techy thermal, this ultra soft jacket is an easy staple in any rider’s closet.

Aztec Diamond Equestrian Tech Base Layer – $52

A slim, black base layer is like an old schoolmaster; it does the job for just about anyone. Stock up on this inexpensive version that also comes in many additional color variations.

Patagonia Capilene Air Hoody – $149

A blend of Merino wool and recycled polyester makes this wicking thermal warm and quick-drying. With a snug fit and a seamless design, it’s the perfect base layer for frigid temperatures. This “Arrow Red” one is a very current color and is manufactured by Patagonia, which makes it a no-brainer.

California Dreamin’ Sweater – $299

A perfect layering piece for transition days, and given its adherence to today’s retro fashion trends, this sweater is what we like to call “street to stable,” as opposed to the other way around. Plus, it’s made of ethically sourced Merino wool, and we feel good about that.

FUTI Boot Covers – $20

Okay, maybe these aren’t the most stylish item on our list, but we are anti-frozen toes. These fit over a variety of boot styles, and we recommend buying them a size too large to help trap warm air (it works!).

Lulu Lemon Cross Chill Earwarmer – $28

Fits under a helmet. Enough said.

Drunk Elephant Lippe Balm – $18

Because a wind-whipped pout is no fun. This buttery balm contains a plethora of antioxidants to combat aging, and there are claims that it even plumps and defines the lip line.

Horze Avalanche Quarter Sheet – $40

What kind of horsewomen would we be if we didn’t consider the warmth of our horses? We love our custom Blue Ribbon Blankets quarter sheets for chilly show days or hacks out in public, but for everyday riding, this Horze sheet is a go-to. The nylon material sheds dirt, prevents rubbing, and blocks the wind, while a small amount of insulation traps heat, because everyone knows a warmer horse is a safer horse!

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