What To Wear For a Trail Ride

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So, you want to try a quick horseback ride on vacation, but you’re not a rider. What should you wear? In part, of course, this depends on the climate, but I have some basic guidelines.

A Helmet

Yes, there are places that let you ride without them and even that actively discourage it. Please wear a helmet. Find out ahead of time if the place you intend to ride has loaners. If not, you can get a cheap helmet at tack stores, farm supply stores and even big box stores in rural areas. Helmets can be had for as little as $50. Compared to the cost of your vacation and the value of your head, that’s nothing.

I don’t suggest ordering a helmet online if you have never worn one before as you need to know your size and which style is most comfortable. Your helmet should not give you a headache (if it does it’s too small), and should stay in place when you vigorously jump up and down (if it moves, make sure the harness is tight).

All helmets are made to certain standards. On the more expensive ones you’re paying for style and appearance, something that doesn’t matter for casual trail riding.

Proper Footwear

Despite being mentioned first, helmets are not the most important safety gear. They’ll help you if you’re in a bad accident.

Proper footwear will help you all the time. Obviously, the ideal is proper riding or cowboy boots, but English riding boots start at about $80 and they aren’t much use for anything else. (Trust me, you don’t want to try and walk any distance in them).

If you don’t want to spend that, then the basic rule is “Closed toe, and at least an inch of heel.” Boots are better than shoes because ankle support helps your comfort. Do not ride in sneakers, tennis shoes, or hiking boots. Sneakers specially designed for riding are available but, again, are kind of expensive. There are two things you have to think about:

  1. IF you fall off (which is unlikely on a tourist trail ride, they choose horses that half the time can’t be bothered to move), then your foot may slide through the stirrup or otherwise get stuck in it. Then you can get dragged, resulting in significant injury. Hiking boots will get stuck.
  2. Horses don’t always look where they are putting their hooves. Or if you make them mad enough, sometimes they will aim. Open-toed shoes or bare feet do not get on well with 1,000 pounds of animal stepping on your foot.

If you happen to have ankle fashion boots with a slight heel, those are ideal. Look through your wardrobe and see what you have. Don’t wear boots you are hugely fond of or ones which are hard to clean; you’re very likely to get mud and worse on them.


I recommend jeans on your lower half. Proper riding pants are better because they don’t have an inside seam, which can rub. But especially in a western saddle, jeans are fine. I’ve done multi-day endurance rides in jeans, because English breeches don’t actually get on well with western fenders.

Don’t wear your best pair, and don’t wear pairs that have holes in them. Loose jeans are better than skinny jeans, which can interfere with getting on.

If you aren’t a jeans wearer, khakis and chinos may also work. Never ride in shorts (unless it’s bareback and you’re riding on the beach and plan on going in the water). You will regret it if you try. If you wear a modesty skirt, wear leggings or similar underneath.

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Photo by Parker Burchfield on Unsplash


It doesn’t really matter what kind of top you wear for riding. If you’re going into the mountains, please wear a long-sleeved shirt no matter how warm it is. Sunburn at altitude is no fun.

Otherwise, you can ride in a regular t-shirt or button down. Again, don’t wear anything you don’t mind getting dusty or even muddy. You generally want to tuck your shirt into your pants so it doesn’t flap.

Rain Gear

You will absolutely want rain gear for multi-day trips and it’s a good idea to bring it for shorter rides.

Long coats and horses do not get on well. What you want is a short slicker and, trust me, rain pants. Rain pants are also handy for hiking and good to have in your wardrobe in general.

Make sure any jacket you wear is fairly short otherwise it will bunch up in the saddle seat and/or flap around. The first will annoy you, the second will annoy the horse.

The absolute most important thing, though, is proper footwear. I wince any time I see people even approach a horse in sandals…

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Freelance writer, freelance editor, novelist and short story writer. Jack of many trades. https://www.jenniferrpovey.com/

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