How to Dress for Winter Riding

Riding and working in the barn in the cold can really take it out of you, so it’s important to know how to dress. Dressing correctly is the difference between frostbite and slightly chilly comfort. Here are some must-haves for riding and working around horses in the winter months.

I’m a bit of a rara avis in the equestrian world; a riding instructor and horse trainer, who *insert gasp here* actively likes winter. Like Lorelai Gilmore, I wait all year for those first flakes of snow, and the quiet and calm that winter invokes.

It’s a time of reflection, when we are forced to take a step back from the bustle of our normal daily lives by the fact that it gets dark circa 4 PM. And before any of my readers shout that I’m just someone sitting on my couch with a cup of tea, I do actually own and care for my own horses (right now there are more horses on my property than I would like to admit to my husband, so we’ll just say horses and leave it at that). And while, yes, at this moment, I am firmly ensconced in three blankets with a steaming cup of Orange Pekoe tea sitting at my right shoulder, I do, indeed, do more than my fair share of de-icing water buckets and scooping frozen poop. 

So, this deep-seated love of that most hated of seasons, winter, has made me desire to spread my knowledge of how to dress warmly for the winter with my riding students. Now, when I am riding at home, I am riding out in the open — in a field, or on a road, and there is absolutely no wind break on my property. At work, we have a heated barn, and a lovely indoor riding arena, so my advice for how my students should dress is often different from how I would personally dress to ride. And how I dress to ride is very different from how I dress to teach — the riding instructors who are reading this feel what I am talking about in their souls. When you are instructing, and you are just standing in an arena hour after hour, you get cold; a deep, bone-chilling cold that even the biggest pot of hot cocoa cannot cure. 

In this article, I’m going to walk through some of the essentials for winter riding. For those of you who hate cold weather, or who, like me, ride in high winds in open fields, I’ll provide some serious options. And for those of you, like my students, who mainly ride indoors, I’ll provide some less drastic options. So, if you are just totally over the winter doldrums, and you’re desperate to warm up, grab a cup of tea, and enjoy some internet shopping. 


First up, gloves, because keeping your hands warm is essential to surviving the winter months. For those of you, who ride mainly indoors in the winter, you can’t beat these fleece-lined SSG winter gloves. They are not bulky, and feature grippy bumps that make holding onto the reins easy. 

The SSG Winter Lined Rancher is my go-to winter glove. I ride in these. I use them for barn work. These aren’t quite up to the coldest, blustery days on the farm when I’m riding multiple horses. But they are perfect for teaching riding lessons, or a winter trail ride. 

I have spent several winters riding in these Heritage Extreme Winter gloves. They are exceptionally comfortable to ride in and are not bulky. But they have the added benefit of also being comfortable to do stalls in. 

Personally, I am a mitten person when I am riding on the very coldest of days and I turn to these amazingly warm riding mittens from Ovation. They have a lovely grippy surface, they attach around your wrists comfortably, and they feature a place for your pinky. Because they are mittens, they allow your three central fingers to nestle together. And if you are really desperate, you can add hand warmers in the central location.

Hats and Headbands

Next to your hands, keeping your head warm is one of the trickiest parts about winter riding. Hats are often too bulky to wear under your helmet in the dead of winter, so I tend to favor headbands. But in this section, I’ll give you some of my favorite hats and headbands for the winter months. 

I am obsessed with the Chelonia Double-Layer Fleece Band from Turtlefur. It is warm and snug, and comes in a variety of colors at a low price point. And for you people who don’t need as serious a headband, it also comes in a single-layer fleece variety. 

When, I’m really cold, and I’m willing to swap out a headband for my riding, and a hat for my barn work, I tend to favor Carhartt Hats. I like their knit beanies that come in a variety of colors at a low price point. But if I’m spending long hours outside, and I don’t want to look like a lumberjack, I tend to favor one of their fleece-lined knit hats.

Neck Warmers

For me, the key to being able to spend long hours outside in the winter is keeping my neck warm. The idea of riding a horse while wearing a long scarf has always kind of freaked me out — maybe it’s the fact that my riding instructor used to warm me about wearing necklaces when riding, or my grandmother’s fascination with Isadora Duncan, but either way scarves are a big no for me. But, as an alternative, I do love cowls, wild rags and neck gaiters.

Wild rags are both functional and beautiful. They add a little pizazz to every outfit. And you know the English riders out there, are just waiting to get their hands on one to try to up their matchy-matchy game. Winter is the perfect time to add one to your outfit and keep your neck and chest a bit warmer. I particularly like these wild rags from the Thrifty Cowgirl

When it comes to neck gaiters the tube style is my favorite and I especially love fleece-lined option, like the Pipe Dream Performance Fleece Neck Gaiter from Turtlefur

Wool cowls are a beautiful, functional option for those of you who spend serious hours in the saddle in the winter. Like these available from Etsy and made with Pendleton fabric


For keeping your core warm, there is nothing like a vest. And you can layer them under a jacket, so if you’re riding in an arena, you can easily remove a layer.

For warmer days, I like a nice, lightweight fleece vest, like this one from Kerrit’sAs the temperature drops, I move to a quilted vest, like the Piper Down Vest by SmartPak.

And for those of you, like me, who spend many hours in the cold, a heated vest is an absolute must. Ororo makes wonderful heated products.

Boots and Socks

Keeping your extremities warm is one of the most important parts of staying warm in the winter. Frozen feet are especially unpleasant. So, we’ll move on to socks and boots. 

For barn chores and riding instruction, I am a big fan of Dry Shod boots. I am hard on boots and mine have lasted me many seasons. For my serious winter rides, I tend to favor Mukluks. They can be waterproofed to keep your feet dry, and are comfortable to ride and walk in. These Ariat Extreme Tall H20 Insulated Boots are also wonderful for both winter riding and for winter horse chores.

For long hours outside in the winter standing around, nothing beats the heated socks from Ororo. Trainers and riding instructors know what I’m talking about. 

I have what my mother affectionately refers to as “muscular legs” so, when I’m riding in the winter, I like socks that are wide enough to cover my calves, like these Darn Tough Mountaineering Over The Calf Winter Socks


And lastly, let’s talk about outerwear: jackets, bibs, skirts, capes, and bodysuits. 

Trainer’s coat: I have a couple of go-to barn coats, but when my current favorites die, I already have my eye on this beauty from SmartPak. It’s called the Hadley Down Trainer’s Coat, and it looks as soft and comfortable as a day spent lounging wrapped in multiple blankets writing this article. It has several features to make it comfortable to ride in, and is also oh so easy on the eyes.  

My favorite winter-riding purchase is my Arctic Riding Skirt. It keeps me warm in the winter but also repels rain and works as a quarter sheet for my horse. The Arctic Skirt brand is currently in hibernation, but similar riding skirts can be found on Etsy, or with my friends at Kin’s Customs.

Speaking of Kin’s Customs, they make the coolest riding cloaks, and my next purchase is definitely going to be a riding cloak, because it’s like a riding skirt and a coat had a happy little baby. And who doesn’t like staying warm while looking like a Disney Princess in the process?

And now for the times when I decidedly don’t look like a Disney Princess, when it’s too cold outside for me to contemplate going outside without freezing, I bundle myself up in either my Carhartt body suit or my Carhartt bibs (depending on the severity of the cold). Bibs mean it’s not that bad out. My breaking out the body suit means that even I am cold. I buy the men’s version. And they are big and bulky on me. They are lined and warm. The fawn colored canvas does nothing for my complexion, and an added bonus is that they make me look no less than 20 lbs heavier than I am. So, come spring, everyone thinks I look great.   

What are some of your tips for staying warm in the winter? Do you have favorite winter riding outfits? Drop them in the Facebook comments!