Horse riding in The Last Best Place? Dress the part.
Horses were the first thing that attracted me to Montana on a Big Sky Yoga Retreats vacation, and they’re a big part of why I later decided to move here and get my first horse. It was the best decision I ever made, and I can’t imagine a better destination for equestrians of all levels.
Wear long pants, like jeans, to protect your legs from the tack and natural elements you may come across on the trail.
Wear boots with a low heel (preferably waterproof) so your feet don’t get caught in your stirrups and to protect your toes if you accidentally get stepped on.
Wear a fitted long sleeved shirt that protects you from the sun and tree branches.
Wear layers you can add and remove in case the weather changes (virtually guaranteed in Montana), like a vest, raincoat, scarf, gloves, and insulated jacket.
Now that you have a sense of the basics, let’s dig into the details of what to wear, including a few of my favorite “Montana essentials.”
Love yoga and horses? Big Sky Yoga Retreats offers luxury women’s yoga and horseback riding vacations in the wilds of Montana. Use Referral Code “HRcowgirlup” during registration for a special gift upon arrival!
How the West Gets Dressed
Whether you’re planning a casual trail ride with friends, taking a pack trip with a professional outfitter, or are staying at a dude ranch for the first time, it’s important dress with the following priorities in mind:
Safety: You can’t revel in our majestic scenery if you’re hurt, so priority numero uno is staying safe. That means “protecting your melon” (i.e. wearing a helmet), choosing boots that are safe for riding, and avoiding clothing that could become tangled in your tack.
Comfort: Montana horseback rides can vary in length from short beginner rides (<1 hour) to overnight backcountry pack trips. Making sure you’re comfortable for the entirety of your ride allows you to focus on your horse, the nature around you, and friends (old and new)–not on your aching feet and blistered hands.
Weather: “If you don’t like the weather in Montana, wait five minutes.” This popular local sentiment based on the fact that the state’s weather is constantly shifting. What you wear should allow you to easily adjust for temperature shifts, precipitation, wind, and other changes while you’re far from the car.
Terrain: Riding in Montana is the real deal. On a single ride, you may find yourself climbing mountains, descending into valleys, crossing rivers, and navigating natural obstacles like fallen logs, rocks, and dense forests. Your outfit should be suited to whatever challenges you may come across courtesy of Mother Nature.
Adjustability: Staying flexible is key when you’re riding horses in Montana, and I always recommend wearing clothing that allows you to add/subtract/adjust items as conditions change. I’ve been on trail rides where it’s warm and sunny when we set out only to turn into rain or snow as we gained elevation.
Authenticity: Riding horses in Montana isn’t just about the activity, it’s about the “feeling.” You want to look the part, blend in, and embrace your inner cowgirl or cowboy. This article will help you look like one of us locals–not a tourist.
Note: We’ll talk about some must-have supplies you should take on your trail ride or pack trip later in this article.
Made (to Ride) in Montana
For those who are new to horseback riding and experienced riders who simply haven’t been to Montana before, we’ll walk through what to wear from head to toe.
Helmet
Please don’t stop reading if you disagree with me on this one. I understand full-well that the quintessential western rider in your mind probably isn’t wearing a helmet
Don’t be surprised if you’re one of the few (or the only one) wearing a helmet in your group. It’s happened to me many times.
Unfortunately, many Montana riders wear cowboy hats instead of helmets–and there are a lot of avoidable injuries as a result. One of my friends had to be airlifted off a trail a few years ago after her horse tripped on some rocks and she suffered a traumatic brain injury (TBI).
Luckily, she WAS wearing her helmet, and it likely saved her life.
The point is, putting “fashion” over safety is short-sighted, especially now that you can have both. My western-style Troxel Sierra helmet fits in perfectly on trail rides so I “blend in” and have piece of mind knowing I’m protecting my melon.
When it comes to Montana horse riding, your best bet is to wear a comfortable collared long-sleeve shirt.
It not only protects you from the sun (We’re close to nature and the sun up here!), it protects your arms from tree branches, allows you to roll up your sleeves if you get too hot, or roll them down if it’s chilly.
Note: If you’re riding here in peak summer heat, Kerrits makes a great long sleeve and short sleeve shirt for staying cool. I wear their Ice-Fil products all summer long because they keep me cool, are super light to wear, and come with UPF 30+sun protection.
Safety Vest
While not required, a safety vest may be a good addition if you’re new to horseback riding or will be on a particularly challenging trail. Vests provide a lot of protection for your ribcage and core (and all those important organs!). The key is to buy one with side protection (not laced sides).
I’ve had my Aerowear Outlyne for two years ago and love it. It can get pretty hot in the dead of summer though.
Gloves
If you’re going on a longer ride (2+ hours), I recommend wearing gloves to protect your hands against reins friction. For ladies, go with the SSG Hybrid Gloves. They’re super soft and flexible, and they have a lovely western style.
For gents, the SSG Rancher Glove is a solid choice.
I’ve also found Mountain Horse Crochet Everyday Riding Gloves to be great for warmer weather. The crochet backing makes them the coolest gloves for hot weather riding, and the leather palm is high-quality, flexible, and fits like a… glove.
The most popular riding pant in Montana is blue jeans, especially if you’ll be riding in a western saddle. All jeans aren’t made equal though, so the ones you’re used to wearing may or may not fit the bill for your trip.
Pick a jean with flat inside seams so you don’t rub your legs raw against the saddle and pant legs long enough not to shimmy up and over your boot while you’re riding.
If you’re going to be riding for several hours on the trail or frequently swinging into the saddle on a longer pack trip, it’s worth investing in a flexible pair of jeans specifically made for riders. Wrangler makes a suitable jean for ladies called (ta-da) The Ultimate Riding Jean.
Choosing the right underwear for your trip is more important than you might think. Chafing, pant lines (for us english riding ladies), and general discomfort can cut your ride short.
Best horse riding underwear for women: Underarmour compression shorts are a really popular choice for ladies. They’re form fitting, lightweight, wick moisture/sweat, quick drying, super stretchy, have a wide comfy waistband, won’t give you panty lines, and feature anti-odor technology. Maidenform makes a similar boyshort (non-compression) that’s a bit cheaper, too.
Best men’s underwear for horseback riding: Underarmour has a men’s compression short that ticks all the boxes for gents on a trail ride. They’re lightweight, wick moisture/sweat, quick drying, super stretchy, have a wide performance waistband, and feature anti-odor technology.
Half chaps slip on over your paddock-style boots (like these) and pants and zip up the side to just under your knee. They protect your leg from rubbing and also keep your pants protected from wear and tear.
The Ariat Terrain II is a solid option and easy to pack in your luggage.
If you’re heading out for an all-day or overnight trip, it’s worth investing in a pair of full chaps or chinks. Both can be worn over your jeans to provide greater protection from weather and natural elements.
I once made the mistake of gathering cattle with a friend in a densely forested area without my chaps, and I got poked by too many branches to count along the way.
Many riders in this area wear belts, but they don’t have to be fancy. Gents can go with something like this simple Nocona, and ladies can try the Ariat Fatbaby.
It looks great with everything and lasts forever.
Boot Socks
No need to get too complicated, but you do want to wear nice tall socks (at least calf height) that won’t slip or cut off your circulation after hours in the saddle.
Grab a few pairs of TuffRider CoolMax boot socks (warm weather) or Storm Block winter boot socks (cold weather), and you’ll be ready to hit the trail.
Since you’ll likely be wearing jeans on your ride, choose boots that’ll look great and keep you safe on and off your horse.
The most important thing is to have a distinct heel so your foot can’t accidentally slip through the stirrup, so no tennis shoes, sandals, or flip flops!
The classic riding choice out here is a cowboy boot. (Warning: It’s hard to stop at just one pair!) Tempting though it may be, don’t buy a purely fashionable boot. You need boots that are comfortable enough for riding and that you won’t freak out about if they get dirty, scuffed, or stepped on (which they will).
The Ariat Autry (ladies) and Ariat Rambler (gents) are both great options.
My personal favorites are my Merrell Captivas. I’ve worn them going on five years (3-5 times per week), though I also own a nice pair of Ariats. Both are comfy, waterproof, and look great with jeans.
You can also go with a western paddock boot like the Ariat Heritage Lacer II (ladies) or the Ariat Quest (gents).
Note: Invest in a can of waterproofing boot spray if your boots aren’t waterproof already. Riding down the trail with soaked socks and wet feet is miserable!
Layers, Layers, Layers
Aside from wearing a helmet, this is probably the biggest takeaway when it comes to Montana riding wardrobes. Always take a vest, jacket, raincoat, or all three on your ride. (If you’re borrowing or renting a horse, you’ll probably get a set of saddlebags you can put extra gear in–or you can tie extra layers to your saddle with the attached straps).
Also, wear clothing that’s short enough in the back so it doesn’t get caught on the back of your saddle.
Choosing a true riding jacket will ensure you stay both fashionable and safe in the saddle. The Kerrits On Track Riding Jacket is currently in my cart, and I love the horseshoe stitching, ladies slim fit, and full zip.
I also ride in my Marmot vest three seasons out of the year. It’s easy to wad up in a saddle bag, throw on over a shirt or jacket for extra warmth, and it’s lasted 5+ years already. Marmot makes equivalent vests for men that are easy to pack on your ride.
This is something most new riders forget, but it’s always a good idea to bring a handkerchief or neck gaiter. You can use it as a dust mask, cooling head cover on a hot ride, or around your neck to block the sun.
I take my Mission Multi-Cool Gaiter on trail rides because it’s got plenty of fabric to pull it up over my nose against dust and wind, or I can dunk it in a stream and cool myself down.
Cowboy Hat (For Breaks)
Just because you ride in a helmet doesn’t mean you can’t bring a cowboy hat for non-riding time. (They’re also great for hiding helmet hair…) The most authentic choice would be a fur felt cowboy hat from a trusted brand like Stetson.
They’ve been making hats for more than 150 years, and they’re the most popular cowboy hat brand in (dare I say) the world. They’re crafted to last a lifetime.
Stetson also makes high-quality wool felt hats. In fact, my favorite cowboy hat is the Stetson Gallatin Crushable Wool Felt Hat. The dark sage/grey color goes with everything, and the subtle leather band is a nice touch.
Plus, as the name implies, it’s made to get smashed, stepped on, and rolled before going back to its original shape as though nothing happened. Talk about a perfect cowboy hat for traveling!
Pro Tips: Vacation Horseback Riding in Montana
Bring your own helmet
Don’t assume helmets will be available when you get to your destination. Call ahead to check, or simply pack your own helmet to ensure quality and fit. Helmets are easier to pack than you think (Troxel helmets are very lightweight).
Place it upside down in your luggage and pack small items like socks and underwear inside.
Love yoga and horses? Big Sky Yoga Retreats offers luxury women’s yoga and horseback riding vacations in the wilds of Montana. Use Referral Code “HRcowgirlup” during registration for a special gift upon arrival!
Hiking/riding combo boots
If you don’t want to pack a separate pair of riding boots or plan human and horse-powered trekking, a hiking/riding combo boot is a great option.
The Ariat Terrain H2O (gents) and the women’s version have the heel you need to ride and the comfort and structure you need to hike. (Check our shopping list for details.)
Denim breeches
Ladies, this is a tip for you. Get a pair of denim knee patch breeches you can wear on your ride or out on the town for dinner. (Though I’m vegetarian, my friends always recommend our bison burgers to visitors.)
Riding in Montana isn’t the same as riding at a local barn in the suburbs. Cell phone service can be very spotty in certain parks and remote locations, and you shouldn’t assume your phone (or anyone else’s) will work in an emergency.
If you get lost, separated from your group, stuck in bad weather, or injured on the trail, you’ll be grateful you packed a GPS satellite phone.
Knowing cell phone coverage wouldn’t be consistent, a sat phone was one of the first items I bought once I decided to move to Montana. My DeLorme InReach device is something I keep in my truck at all time and transfer to my saddle bags for trail rides.
It’s very compact, lightweight, has impressive battery life (it’s never died on me even after months sitting in the car), has built-in navigation, and can trigger an SOS request via two-way text.
Plus, you can use the MapShare feature to send family or friends updates on your location. These devices come with a higher price tag, but it’s well worth the peace of mind for me.
Medical bracelet
Another wise investment (albeit a much smaller one) is a medical ID bracelet. Wearing one of these while riding helps first responders identify you, your key contacts, and any medical conditions you may not be able to share if injured or unconscious.
Since I ride multiple times per week, I went with the Ride Safe bracelet. (I keep one in my trailer and one with my tack in the barn.) But, if I was only doing the occasional ride or trying horse riding on vacation, the RoadID would be completely sufficient.
Altitude adjustments
One of the most common afflictions for visitors is altitude sickness. (Here’s a good article about it if you want to learn more.) Where I live, we’re at nearly 5,000 above sea level. If you’re worried about adjusting, pack some Flygood Travel Vitamins that help prevent altitude sickness.
If you start to feel lightheaded or unusually tired, tell whomever is guiding your trip immediately.
Bring extra bottled water, too, and drink more than you normally would. It helps!
Sun protection
Here’s something most visitors don’t consider enough. Given our high elevation, sunburn and heatstroke are real concerns. Be sure to wear sunscreen, sunglasses, a helmet with a visor (and brimmed hat during breaks), as well as long sleeved shirts with collars.
Adding a handkerchief around your neck helps, too.
Bear spray
Nope, that’s not a joke. We have bears around here, and while it’s unlikely you’ll come across one, you’re better off safe than sorry. If you’re driving to Montana, you should buy it ahead of time and bring it with you.
If you’re flying, however, the TSA prohibits bear spray in carry-on AND checked baggage. So pick up a can once you arrive in Montana. All our sporting good stores carry it, as do many gas stations and airport shops.
Pro Tips: What to Wear Horseback Riding in Montana Summers
Montana summers are beautiful, but also hot. Not only can your horse get overheated, you can too. If you’re going to be riding in the heat of summer or in a spot without shade:
Soak before you go: I use soakable neck wraps, and they’re lifesavers in the summer. Dunk them in a stream or river, and they’ll keep you cool for hours.
Think breathable:Kerrits Ice-Fil Breeches are my favorite pants for hot weather rides. They’re durable but lightweight, and the Ice-Fil fabric can lower skin temperature by five degrees vs. jeans.
Stay hydrated: Bring plenty of water and carry it in a holster that easily clips to your saddle like this. Don’t assume water or holders will be provided (unless you call to check).
Heads up: If you have access to a freezer prior to your ride, toss a few mini ice packets in. I put one in my helmet before riding in the hottest parts of the summer, and it’s made a huge difference. My saddle bags also have an insulated pouch where I can put cold items that need to stay cold.
Pro Tips: What to Wear Horseback Riding in Montana Winters
Though some think I’m crazy, I continue to ride until it’s about twenty degrees. I love strolling down snowy roads and trails in the peace and quiet of winter.
But, winter riding takes some extra planning so your hands, feet, and core stay warm enough to function:
Battery heat: After a freezing cold first winter at the barn, I invested in a my first battery-heated coat. It was life changing. Now I also own a heated vest and heated gloves. I recommend these to everyone.
Insulated boots: I HATE trail riding with cold feet. Now I don’t! After trying several boots that didn’t work at all, I came across the Horze Spirit Montana insulated riding boot.
Shoe inserts: I’ve tried them all (including heated socks which didn’t work at all), and I believe Grabbers heated insoles are the best of the best. You do have to throw them away after each use, BUT they’re so effective it’s worth it. (Read more about these inserts in my monthly expense reports.)
Head heat: Most of your body heat escapes via your head, so put a stop to it. This is the only balaclava I’ve found that is super warm AND fits under my helmet. (It adjusts in the back, so it works for men and women.)
It can quickly become overwhelming to remember everything you need to bring on a ride. I made a checklist on my phone so I can quickly glance at it before I hit the trail.
Apparel
Helmet
Shirt(s)
Pants
Rain jacket or slicker
Jacket
Boots (spurs if you’re experienced)
Change of clothes for once you return
Belt
Gloves
Half chaps or full chaps
Cowboy hat / Baseball hat for rest breaks
Other Gear
Water
First aid kit (I keep this mini kit in my saddle bags.)
Neck gaiter
Chapstick
Cell phone
Sunscreen
Sunglasses
Snacks/food
Fly spray
Bug spray
Cell phone holster (This is the one I use and LOVE.)
Horse riding vacations can be a great way to explore a new place without all the hiking. There are options available in many countries and for all levels of riders.
While some offer lodging along the way, the best horse vacations are an immersion into nature and involve camping along some strikingly scenic routes.
You can choose something rustic such as learning to herd cattle or go to Europe and explore old mountain trails. On a budget?
Many local places offer trail rides for anywhere from 1-3 hours. Wherever you choose, call ahead to make sure they have horses suitable for your riding level.
Q: Is Montana a good place to vacation?
Definitely! It’s not known as Big Sky Country for nothing. You can have your pick of national parks and lively cities, all with a little Western flair.
If you’re a history buff, check out the Little Bighorn Battlefield National Monument where Custer’s Last Stand occurred in 1876.
More of a city person? Plan a stop at Helena, the state’s capital, or Missoula. Water lovers will enjoy a trip to Flathead Lake or Great Falls.
Then, there’s always the classic option to visit Yellowstone or the beautiful Glacier National Park. Plus, there are options for trail riding or dude ranch stays across the state.
Q: What shoes to wear horseback riding?
Good riding shoes can make or break your ride (and your feet). Check out these articles for guidance:
Q: What should you wear if trail riding or horse riding at night?
All of the apparel advice in this article still applies to night riding, but there are a few extra items you’ll want to take along:
Light Source: Horses can see just fine at night (even better if you don’t shine a flashlight in their eyes…), so don’t feel like you need to bath the trail with light. Even your eyes will adjust if you give them a little time. Regardless, you should bring a flashlight in your saddle bags and a headlamp in case you need them during the ride. (Here’s the headlamp I have, and it’s super comfortable and has four lighting modes.)
Reflective Clothing: Wearing reflective and light colored clothing is a must for night riding. It can be as simple as buying an inexpensive reflective vest (this one comes with arm/ankle bands). If you want to go a step further, pick up reflective leg bands, reflective bridle tubing, and/or a lighted breast collar for your horse.
Love yoga and horses? Big Sky Yoga Retreats offers luxury women’s yoga and horseback riding vacations in the wilds of Montana. Use Referral Code “HRcowgirlup” during registration for a special gift upon arrival!
Welcome to Montana, pardner!
Prepare to be wowed by Montana!
Whether you’re riding in Glacier National Park, touring Yellowstone National Park, enjoying one of our any state forests, or trying a dude ranch, Montana’s many wonders look even more magical by horseback. I can’t wait for you to experience them yourself.
When riding in Montana, dressing appropriately for the terrain and weather is essential. Given the diverse landscapes, it’s crucial to be prepared for various conditions. In summary, I’ve learned that a few staple items are key. For starters, I always opt for jeans—ones that have flat inside seams to prevent chafing during long rides. For comfort and safety, investing in good cowboy boots with a distinct heel to prevent my foot from slipping through the stirrup is a must. Layering is crucial due to unpredictable weather changes. Wearing a comfortable collared long-sleeve shirt provides protection from the sun and branches while allowing for temperature adjustment by rolling up the sleeves. Additionally, I often wear a durable jacket, considering the sudden temperature drops. Carrying a waterproof one is a smart move, too.
Helmets are a non-negotiable safety measure, regardless of the varying practices among riders. For longer rides, I wear gloves to protect my hands and ensure a better grip on the reins. I also consider wearing a safety vest, especially if the trail presents challenges or steep paths. When packing, essentials like a neck gaiter, sunscreen, and sunglasses are always in my kit. Footwear and clothing should be practical and comfortable, allowing freedom of movement.
Understanding the environment and the ever-changing conditions while riding in Montana has taught me the value of being adaptable with my attire, focusing on safety, comfort, and flexibility.
From the tender age of six, I embarked on a journey that would weave horses into the very fabric of my existence. Over 35 years have passed since I first mounted a horse, and my love for equestrian sports is stronger than ever before.
