Happy Trails Gear Guide: What to Wear Horseback Trail Riding

Trail tested, wallet approved horse riding essentials

Trail riding has been part of my life since childhood, and I’m now getting back into it as an adult with the first horse of my own. I’ve enjoyed trail rides through Midwest parks, across Arizona deserts, along the coast of Prince Edward Island, on the beaches of Puerto Rico and Costa Rica, and now in the Rocky Mountains. One thing I’ve learned: regardless of where you’re riding, what you’re wearing when you hit the trail (especially if literally…ha) is critical to your fun and safety.

If you’re going horseback trail riding and wondering what to wear:

• Wear an ASTM/SEI compliant horseback riding helmet. (I wear this western style one from Troxel.)
• Wear long pants like jeans, breeches, or jodhpurs to protect your legs from the tack and natural elements 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, like a vest, raincoat, scarf, gloves, and insulated jacket.

Now that you have a sense of the basics, we’ll dig into the details of how to dress for a trail ride, including several of my favorite “trail essentials” I never ride without. (Speaking of essentials, be sure to check out our Ultimate Packing & Horse Trailering Checklist before you hit the road.)

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Outfitted for Success

Whether you’re heading out on a casual trail ride with friends, taking a pack trip with a professional outfitter, or eager to explore the trails around your own property, it’s important to dress with the following priorities in mind:

Trail riding is a fun way to bond with your horse.

• Safety: You can’t have fun if you get hurt, so your first priority is staying safe. That means “protecting your melon” (i.e. wearing a helmet), making sure your boots are safe for riding, and avoiding clothing that could get tangled in your horse’s tack.
• Comfort: Trail rides vary in length from short beginner rides (<1 hour) to multi-day backcountry pack trips. Making sure you’re comfortable for the duration of your ride helps you focus on your horse, beautiful scenery, and friends… instead of our aching feet and blistered hands.
• Weather: How you dress depends on the weather where you’re riding (humid beach ride vs. rainforest ride). Be prepared for temperature, precipitation, wind, and other changes while you’re far from the car.
• Terrain: Trail riding between Arizona cacti brings different challenges than riding through the dense forests of Tennessee or the sun-soaked beaches of Florida. Dress for the specific terrain where you’ll be riding. (And remember terrain may vary within your ride.)
• Adjustability: Staying flexible is key when you’re trail riding, so wear clothing that allows you to add/subtract items as conditions change.

Note: We’ll talk must-have supplies you should take on your trail ride later in this article. Or go ahead and check out our Trail Riding Essentials shopping list here!

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Hitting the Trail (After You Get Dressed)

For those new to horseback riding and riders who simply haven’t done much trail riding, let’s walk through what to wear from head to toe.

Helmet

Every time, every trail ride, wear a properly fitted ASTM/SEI certified helmet. Don’t be surprised if you’re one of few (or the only one) wearing a helmet on your trail ride. (Don’t assume helmets will be available if you’re paying for a trail ride at a park or stable. Call ahead to make sure. Or, better yet, bring your own so you know it fits.)

Unfortunately, many trail riders don’t wear helmets–and there are a lot of avoidable injuries as a result. One friend 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! I wear a Troxel Sierra helmet on trail rides so I “blend in” with fellow western riders while staying safe. This helmet is really popular on the trails, at western shows, and in organizations like 4-H because of its western design and top safety ratings. (Check out the reviews on Amazon.)

If subtlety isn’t your style, head over to the Fallon Taylor Helmet Collection from Troxel. Fallon is a professional barrel racer who suffered a bad fall that made her realize the importance of wearing helmets. She’s bringing her flair for fashion into the western world, and I’m SO grateful more riders are wearing helmets because of her.

Note: Fallon also has a really inspirational (and funny) YouTube channel.

Shirt

When it comes to trail riding, you’ll want to wear a comfortable collared long-sleeve shirt. This not only protects you from the sun, it protects your arms from tree branches (I’ve been hit many times!), and it allows you to roll up your sleeves if you get too hot or keep them down if it’s chilly. Find all our top choices on our Trail Riding Essentials Shopping List, including:

• Ariat Lottie Snap (Ladies)
• Panhandle Slim Blue Arrow Print (Ladies)
• Cowgirl Up Vintage Washed Plaid (Ladies)
• Ariat Classic Button Down (Gents)
• Ariat Fitted Button Down (Gents)
• Rodeo Clothing Co. Cowboy Pearl Snap (Gents)
• Cinch Modern Fit Plaid (Gents)

Note: If you’re riding somewhere especially hot (e.g. the beach) Kerrits makes a great short sleeve option for staying cool called the Breeze Ice-Fil. I wear these all summer long because they let the breeze through and look good with my english breeches and western jeans. (Tank tops don’t provide any sun coverage or protection if you fall off.)

Safety Vest

While not required, I do recommend a safety vest if you’re new to horseback riding (of if you’ll be doing a particularly challenging trail with steep drop offs or jumps along the way). They provide a lot of protection for your core (all those super important organs!) and your ribcage. The key is to buy one with side protection (not just laced sides). I bought the Aerowear Outlyne two years ago and love it.

There are also inflatable equestrian air vests, and I got the Hit Air SV2 for jumping and cow work. I wrote an article about my first fall in my air vest here.

Gloves

If you’re going on a longer ride (2+ hours), I recommend wearing gloves to protect your hands from the reins. I’ve found Mountain Horse Crochet Everyday Riding Gloves to be the best. 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. I also prefer not having a tight velcro closure on the wrist when I’m riding, so these are perfect.

Ladies can also try the SSG Hybrid Gloves. They’re super soft and flexible, and they have a great western style. For gents, the SSG Rancher Glove is a nice choice.

Find them all on our trail riding shopping list.

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Jeans

The most popular trail riding pant is jeans, especially if you’re riding in a western saddle. All jeans aren’t made equally though. You want flat inside seams so you don’t rub your legs raw against the saddle, as well as pant legs long enough not to shimmy up and over your boot while you’re riding. (See our top choices here.)

If you’re going to be riding for several hours on the trail or routinely swinging into the saddle on a long pack trip, it’s worth investing in a pair of jeans specifically made for riders. Wrangler makes a great jean for ladies called (appropriately) The Ultimate Riding Jean. They also make a Retro Jean for Men that’s designed for riding and gets great reviews. I also wear my everyday Flying Monkey skinny jeans on trails because they’re suuuppper soft and stretchy with low-profile inner seams.

If you’re heading out with a group of english riders instead, you may prefer a comfy “riding tight.” I like riding in my Kerrits Ice Fil Tech Tight, especially in warmer temperatures, because they’re lightweight, have grippy knee patches, and have a really comfy wide waistband I can wear all day.

Note: Equestrian Vlogger and horse trainer Shelby Dennis also includes her favorite Wrangler jeans in her Horse Rookie Equestrian Gift Guide. 

Non-Chafing Underwear

Choosing the right underwear for your trail ride is more important than you might think. Chafing, pant lines (for us english riding ladies), and general discomfort can cut your fun short.

• Best horse riding underwear for women: Underarmour compression shorts are one of the most popular choices 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 on your bum, 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.

See our Trail Riding Essentials shopping list for details.

Full or Half Chaps

If you decide to trail ride in shorter cowboy boots or paddock boots, you’ll want a good pair of half chaps. These slip on over your boots and pants and zip up the side to just under your knee. They protect your leg from rubbing and also save your pants from wear and tear. The Ariat Terrain II and Ovation Ribbed Suede are great options. Half chaps are also easy to pack in your luggage if you’ll be riding on vacation.

If you’re riding closer to home, or for an all-day or overnight trip, you may want to invest in a pair of full chaps. These can be worn over riding tights or jeans and with paddock or cowboy boots. They provide the fullest protection from weather and natural elements as they span the entire leg from waist to ankle.

I got a used pair a few years ago, but they no longer fit. (Too many riding muscles?) So I’m back in the market and considering either the Tough 1 Show Stopper Equitation Chaps or ProChaps Athletic Full Chaps.

You can also get full Custom Chaps from Dover Saddlery, but they’re pretty expensive. Unless you’ll be riding a lot, there’s no reason to spend this much. The other chaps above are a better buy.

See our Trail Riding Essentials shopping list for details.

Belt

Many trail riders wear belts, but they don’t need to be fancy. Gents can go with something like the simple Nocona, and ladies can try the Ariat Fatbaby. It looks great with everything and lasts forever. (Both are on our shopping list here.)

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.

Note: Check our shopping list for details, or read about vlogger Shelby Dennis’ favorite boot socks in her Horse Rookie Equestrian Gift Guide. 

Boots

Since you’ll likely be wearing jeans for your trail ride, you should wear 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 trail riding choice is a cowboy boot. Tempting though it may be, don’t buy a purely fashionable boot. You need one that’s 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 starter options.

My personal favorites are my Merrell Captivas. I’ve worn them going on five years (3-5 times per week), and I can’t remember the last time I wore other boots on the trail. They’re 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).

See our Trail Riding Essentials shopping list for details.

Pro Tip: Invest in a can of waterproofing boot spray if your boots aren’t waterproof already (or if you want to give them extra protection). Riding down the trail with soaked socks and wet feet is miserable!

Layers, Layers, Layers

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 saddle straps). 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. (Find both on our shopping list.)

Handkerchief or Gaiter

You can’t go wrong bringing along a good handkerchief or neck gaiter on your trail ride. You can use it as a dust mask if you’re galloping along in the desert, a 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.

What Else to Pack: Horse Trail Ride Checklist

Getting to the middle of nowhere and realizing you forgot something important is a sinking feeling.

If you’re anything like me, it can easily become overwhelming trying to remember what to bring on a trail ride. I made a checklist on my phone so I can quickly glance through it and make sure I have everything.

(Some of these items won’t apply if you’ll be using someone else’s horse/tack or riding in non-mountainous locations.)

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

Tack

• Halter (ideally a trail halter like this that fits under the bridle or in a saddle bag)
• Saddle
• Saddle pad (check out the best trail riding saddle pads here)
• Saddle cushion (I love love the Tush Cush for english and western saddles!)
• Bridle
• Breast Collar
• Saddle bags (I have these Cashel saddle bags, and I love the insulated side for my drinks and lunch.)
• Grooming tote
• Fly mask

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
• Hay net / Hay bag
• Cell phone holster (This is the one I use and LOVE.)
• Safety whistle
• Pocket knife
• Bear spray
• Satellite phone (See the 7 best satellite phones for horse riders)
• Solar charger for cell phone
• Medical ID bracelet
• Helmet cooling inserts
• … And your horse!

Bonus: What to Wear Horseback Riding on Vacation

Horse riding on vacation makes your trip unforgettable.

If you’re going on a horseback riding vacation soon, I’m envious! I love riding on vacation and have ridden across the U.S. and overseas. Here are a few additional pieces of advice, and you’ll find all these items on our trail riding shopping list:

• 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 (and Troxel helmets are super light). Place it upside down in your luggage and pack small items like socks and underwear inside.
• Consider hiking/riding combo boots: Ariat makes great hiking/riding boots that are a versatile choice for vacation. If you don’t want to pack a separate pair of riding boots, this 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.
• Try 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. Goode Rider makes a popular jean breech, and I’ve got my eyes on this dark wash pair from Horze.
• Think about your phone and keys: It’s easy to forget about where you’ll keep your keys and phone while riding on vacation. I got this cell phone leg holster from WoofHoof, and it’s amazing. (The magnet closure doesn’t spook horses like velcro.) Put your keys on a simple carabiner you can clip to your belt buckle or get a slightly bigger water bottle/pocket carrier like this.

Read our entire article about Packing for Paradise: What to Wear Horseback Riding on Vacation.

Not sure where to go? Find a horseback riding vacation through Equitour. 

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Bonus: What to Wear Horseback Trail Riding in the Summer

Summertime riding takes preparation

Trail riding in hot weather is no joke. Not only can your horse get overheated, you can too. If you’re going to be riding in the heat of summer or on the beach without shade:

• Soak before you go: I own several of these soakable neck wraps, and they’re lifesavers in the summer heat. 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 and beach rides. They’re durable but lightweight, and the Ice-Fil fabric is designed to lower your skin temperature by five degrees.
• Stay hydrated: Bring your own water and carry it in a holster that easily clips to your saddle like this. Don’t assume water or holders will be provided.
• Bye-bye bathing suit: Don’t try riding in your bathing suit bottoms or shorts. You’ll rub your legs raw unless you’re riding bareback. That doesn’t mean you can’t wear your bathing suit under your riding clothes so you’re ready once you reach your destination. That’s what I did when I took a trail ride to a waterfall in Costa Rica.
• Heads up: If you have access to a freezer prior to your ride, toss a few of these 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.

Bonus: What to Wear Horseback Trail Riding in the Winter

Horse riding in the winter can be magical–unless you’re freezing!

I’m still out at the barn until about twenty degrees, and I love riding down snowy roads and trails in the peaceful quiet of winter. But, trail riding in the winter takes more pre-planning to make sure I can keep my hands, feet, and core warm enough to function. Find details about each of these items on our shopping list:

• Battery heat: Last winter I bought my first battery-heated coat, and now I also own a heated vest and heated gloves. They’ve. Changed. My. Life. (This brand has stuff for men, too. I got the gloves for my dad, once I realized how amazing they were. He agrees.)
• 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. Granted, they’re not the most attractive boots out there…but they’re the only ones that keep these little piggies from going numb.
• Shoe inserts: I’ve tried them all (including heated socks which didn’t work), and I now buy the Grabbers heated insoles in bulk each winter and put them inside my insulated boots. It is annoying to have to throw them away after one use BUT they’re so effective it’s still worth it.
• Head heat: Much 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.

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Rookie Mistakes (a.k.a. What NOT to Wear Around Horses)

There are a few common fashion faux pas you should avoid when you’re trail riding. Plus, most of these are simply unsafe for riders of any level.

• Yoga pants (find out why)
• Rain boots (find out why)
• Tennis shoes
• Sandals, flip flops, or other open-toe shoes
• Fanny pack (don’t wear one of these anywhere)
• Hiking boots (unless they’re riding/hiking combo boots like these)
• Baseball or floppy hats (wear a helmet!)
• Cutoff shirts that don’t protect your arms
• Cargo pants
• Low-rise jeans (trust me)
• Bathing suit bottoms instead of pants

Frequently Asked Questions

Time to Look Like a Trail Boss

With the right gear and apparel, trail riding is so much fun. You get to see the world from a new perspective, meet new people or catch up with your friends, and spend time with horses.

As someone passionate about hitting the trails on horseback, I wanted to share this guide loaded with must-knows for successful trail riding attire and gear. Safety, comfort, weather, terrain, and adaptability—these principles are key when gearing up for your equine adventure.

I’ve emphasized the importance of safety gear, especially helmets. A harrowing story about a friend’s accident underscored the necessity of helmets, not just for safety but also as a stylish accessory that blends in perfectly with Western riding culture. You’ll also learn things like why wearing a comfortable long-sleeve shirt offers protection from the sun and unexpected tree branches.

The guide also delves into outfit specifics—recommending jeans, gloves, and appropriate boots. We gave a shoutout to specific brands that cater to riding needs, emphasizing the importance of proper fitting and features to prevent discomfort.

Besides clothing, the article highlights additional essentials to pack and considerations for varying weather conditions, emphasizing the need for layers and adaptable clothing choices.

Our checklist for horse, tack, apparel, and other gear was comprehensive, ensuring you won’t forget important items on your next adventure. The tips on horseback riding on vacation, in the summer, and in winter provided practical insights, including innovative ways to stay cool or warm in different conditions.

Furthermore, the “rookie mistakes” section outlines what not to wear, crucial for a safe and enjoyable experience. Overall, this guide is a one-stop-shop for all things horse riding, ensuring a safer and more enjoyable trail riding experience.

If you want more guidance on horse riding equipment, you should also check out these articles:

• 9 Rookie Approved Horseback Riding Boots for Beginners
• 9 Best Boots for Western Horseback Riding
• Making Strides: Sustainability in the Equestrian Industry
• 7 Best Satellite Phones for Horse Riders Who Need Help NOW
• Can you wear yoga pants horseback riding?
• Rodeo Ready or Rodeo Rookie? Depends What You’re Wearing
• Horseback Riding: What to Wear (With Pictures)
• 13 Best Boots for Horseback Riding Lessons
• 9 No-Regrets Riding Breeches
• $hit Happens: 7 Best Boots for Mucking Stalls

Happy Trails!

P.S. New to trailering, but want to hit the trails? You might enjoy You CAN Do This: Trailering a Horse for the First Time.
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