Brrrrr! It’s chilly outside! I guess that’s what happens in the fall. I mean the days are shorter, and well, wintertime means colder riding weather. But this time of year I spend a lot more time riding because it’s November. And I’m riding in not one but TWO No Stirrup November challenges.

Which means cold weather or warm weather, I will be spending a lot more time outside. And I don’t know about you, but I like to stay warm. So there are a few pieces of clothing I find essential in the colder temperatures. And I thought I would share my favorites with you in case you were looking for some tips on how to stay warm while you are riding during the winter months.

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Dressing In Layers

In Colorado the weather can go from winter, to spring, to summer in 3.5 seconds. So I find it best to dress in layers. That way, if it does get warm, I can remove a layer (or two) of clothing without having the police called on me for indecent exposure.

And the layers help this. The bottom layer is the first layer. And typically I wear a slinky style t shirt. Sometimes it’s short sleeved, sometimes it’s a tank top. But something soft against the skin is nice, especially if you are layering.

Next I will wear a long sleeve short, sometimes a sweater. Ok, most of the time it’s a sweater!

And I found this sweater at Old Navy for $12.00!

How To Stay Warm While Riding -Cold Weather Riding Favorites

While I do like ‘equestrian’ clothing, it can be stupidly expensive. So if I can find something that is comfortable, I feel good about myself in, and it’s affordable, I’ll opt for that.

How To Stay Warm While Riding -Cold Weather Riding Favorites

This sweater reminds me of my most favorite Italian riding shirt. But unlike that Italian riding shirt, this one didn’t cost me $118.00! Why is it if it says ‘equestrian’ it is so expensive?

Well this sweater is just the right weight for cooler weather riding, it looks nice, and it’s affordable! You gotta love Old Navy. So this covers layer number one and two on the top. So how about the bottom?

And while I was writing this article , and searching through Amazon I found a GREAT deal on this sweater:

This Kerrits brand Double Diamond sweater was only $27.00! Talk about a deal! Now I bought it in blue, but it also comes in purple for the low price. If you want the tan color, well that is more expensive at $69.00. But I have found Kerrits brand to be very sturdy, and they look so nice! And this will be perfect for layering over the month of November.


I do wear breeches in the winter too. But not the super lightweight kind that many wear during the summer months. No, during the winter I opt for a heavier pair. And these Celebrity Slim breeches by Ovation are my go to cold weather breeches.

I bought them in a bigger size to accommodate an additional bottom layer if needed. But I’m not riding in a cold indoor arena (ever) and I am mostly riding during the day, so typically I am ok with just the breeches. The material is thicker, and keeps my legs warm.

I also like that they are a full seat breech, for extra sticking power. This is especially beneficial when I am riding without my stirrups.


I like riding with a vest when I can. And I found this one at Goodwill for $6.00.

How To Stay Warm While Riding -Cold Weather Riding Favorites

That’s a good deal right? And I do like the faux fur hood. It makes me feel fancy. And if it gets dirty, it’s not a big deal because I only wear this for riding.

I like the vest because my arms are free, and I don’t feel like the little boy from A Christmas Story.


But when the weather gets even colder, I do opt for a heavier coat. It’s not a parka or anything, but it is definitely heavier than my vest.

How To Stay Warm While Riding -Cold Weather Riding Favorites

I got this from Dover Saddlery when they had a sale. But they still have it. It’s made by Riding Sport, just like my new tall boots. And the quality is pretty good. The coat is also lightweight, but it keeps me really warm. Definitely a plus when it’s really chilly.


For me, this is really important. My toes get so cold! So I like to have a heavier sock.

I found these on Amazon, but I think you can find them anywhere you buy riding apparel. They are a wool blend, so they really keep your feet warm. And they are a boot sock, which is perfect for tall boots, and also adding a layer of warmth to your legs.


Now most days, I do just wear my tall boots. But when it gets really cold, I break out my winter riding boots.

I’ve had these for 2 years, and they have held up very well. I wear these whenever there is snow on the ground. And not only for riding, but for all my barn chores. They are thick, and very warm. But they are fashioned after a traditional tall boot. So I can wear them for riding, and they are comfortable enough to wear for long periods of time just being outside.

How To Stay Warm While Riding -Cold Weather Riding Favorites

These are the Horze brand Nome Neoprene boots and I love them. They are waterproof, warm, and I can ride while I’m wearing them.

I leave them zipped up all the time, and just slide them on, which works just fine when I’m wearing my scrubs (for feeding before work) or while I’m wearing my breeches. And with a price tag of around $60.00, they are an affordable winter boot.


I wear gloves about 90% of the time, regardless of the season. But I find them especially important during the winter. My fingers just get so cold! So I have a rather large collection of winter gloves.

I do have a few favorites, but for winter riding I really like the SSG Soft Touch Winter Riding Gloves.

They are comfortable, and I can still use my fingers and feel the reins, or even tightening a girth or changing holes on my stirrups.

How To Stay Warm While Riding -Cold Weather Riding Favorites

The outer layer is a synthetic leather outer layer and lined with silk. They are incredibly soft. And keep my fingers warm while I’m riding without the added bulk of a thick glove.

Ear Warmer

For some, this might sound like an unnecessary extra, but for me, it’s a winter riding staple.

How To Stay Warm While Riding -Cold Weather Riding Favorites

Just like my hands, my ears get cold. Especially if I have my hair pulled back into a pony tail for riding. And I have found that even just a wide headband will work. But I really like the headband I found at Riding Warehouse.

But this year they have some really cute ‘newer models’ and they are adorable! Like this one from Kerrits:

I mean how adorable is this? And Kerrits have some very nice pieces of season specific clothing. But I can tell you about mine, I don’t have this one (yet).

It’s thin, comfortable, and it fits nicely under my helmet without compromising the fit of my helmet. And it keeps my ears warm, and when I take my helmet off, it keep my hair under control too. I call that a multipurpose piece of riding attire that is an important part of my winter riding wardrobe.

How To Stay Warm While Riding -Cold Weather Riding Favorites

Well that about covers my winter riding wardrobe. What about you? Are the things that you wear that keep you riding when the temperature drops? What are your favorites? Please share, because I am always looking for something that keeps me warm, and riding even when it’s cold outside.


I am horse crazy and love DIY projects, and finding great deals on everything horse related. When I have a new idea, or find a great deal I love sharing this information with you........AND just to have FULL Disclosure:Affiliate Disclaimer: Some of the blog posts on my site will allow you to purchase different products and services online provided by other merchants, and not myself. Some of the links that I post on my site are “affiliate links.” This means if you click on the link and purchase the item, I may receive an affiliate commission.* I am a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for me to earn a commission by linking to and affiliated sites. *Disclosed in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

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