Riding Boots on Oahu: Where Are They?
Ready to start your horsemanship journey but struggling to find boots on O‘ahu? You’re not alone! Options are limited, but we’ve got tips to help you find the best pair for your lessons.
Vicky T.
2/7/20266 min read
Are You Ready?
So, you've scheduled your first horseback riding lesson, you've got comfy jeans and you're ready to get your hands dirty...but you can't find any boots to wear. What do you do? One of the most common questions we get at the Academy is where can I buy boots? This might sound like a silly question at first, but it's honestly well warranted.
Have you ever tried to purchase riding boots on island? Have you ever looked? If you have, you'll notice there aren't many options. In fact, there's virtually none. Finding the right boots is an important part of horseback riding, especially for younger students. The right footwear keeps little feet in the stirrups and comfortable during lessons, while also being practical and safe for life around horses. So what are your options?
If you’re new to riding or just starting lessons with us at Hawaii Horsemanship Academy, here’s a quick guide on where you can get your hands on a pair of boots without breaking the bank.
On Island Options
If you’d like to shop in person or try on boots before buying, the reality is you're probably out of luck here on O'ahu. If you've got a four leaf clover in your pocket, here are some options you can try out on island:
Red Wing Stores
(Honolulu & Aiea locations available)
Red Wing is known for durable, high-quality work boots, but do they have any options suitable for horseback riding? The simple answer is yes, they do have some options that will work!
Red Wing's Rio Flex & Heritage collections feature a few Western boots for both men and women, as well as a couple styles acceptable for English-style riding too. However, there are a few drawbacks to buying here. Here's a snapshot of what you need to know:
Pros
High-quality & long lasting
Western boot options for men & women
English-style option for men & women
Cons
Adult sizes only (no kids sizes)
In-store options are limited
Boots are pricey
You can view their selection online, but be sure to call the shop directly to see if they have what you're looking for in stock.
Locations:
📍 Red Wing Aiea 98-1277 Kaʻahumanu St #131, Aiea, HI 96701
📍 Red Wing Honolulu 1130 N Nimitz Hwy Suite A-122, Honolulu, HI 96817
Work Shoe Hawaii
(Honolulu location only)
Work Shoe Hawaii is a locally owned store in Honolulu offering durable footwear for men and women, including safety-toe, slip-resistant, and hiking boots. Included in their repertoire of boot styles are some promising Western boot options for both men & women, but I did not see anything for English style riding while looking through their catalog.
They've been in business since 2013, and the owner himself is from Aiea. We love to support local businesses, so if it looks like a good fit for you, give it a shot! Here's a snapshot of what you need to know before you check the place out:
Pros
High-quality brands (i.e. Ariat)
Multiple Western boot options
Pricing comparable to Ariat itself
Cons
Adult sizes only (no kids sizes)
Small shop (possibly limited sizes)
You can view their selection online, but it might be a good idea to give the store a call to see what's available in your size!
PRO TIP: boots usually fit half a size or a full size UP!
Location:
📍 401 Waiakamilo Rd #102, Honolulu, HI 96817
Local Department Stores
(Walmart, Target, etc.)
If you need riding boots fast or are on a tight budget, Walmart can be a surprisingly decent option, especially for kids’ riding boots. I'm not kidding!
You can often find Western-style look-alike boots or even simply rain boots that will work in a pinch. Please note we only recommend rain boot for kids, not adults! Adult sized rain boots get stuck in the stirrup easily, while the kid's sizes are still small enough to manage.
While these options aren’t true riding boots, they can get you through lessons comfortably until you’re ready to invest in a more specialized pair. This is what we suggest for brand new youth riders.
Here's a snapshot of what you need to know before you check the place out:
Pros
Inexpensive options
Easily accessible (lots of locations)
Lots of available sizes (including kids sizes)
Cons
Questionable durability
Not real riding boots
Local Thrift Shops
(Good Will, Salvation Army, etc.)
It's a hit or a miss, but hey, you might find a needle in a haystack! We've found some good quality riding boots at local thrift shops before. Good news is, if you find a pair that fit, they're probably already broken in and usually pretty cheap! Try your luck if you happen to be nearby.
Online Options
For the best combination of selection, pricing, and shipping, Amazon is hard to beat. You’ll find a wide range of kids’ riding boots, often at great prices and with fast delivery if you already have Amazon Prime. This is what we suggest for parents and youth students looking for quality boots.
While you can also order boots online from direct brands like Ariat, Justin Boots, Durango, etc., keep in mind that Amazon also carries these brands and usually has comparative pricing. Of course, Amazon also features off-brand, generic boots that can fit the bill for what you need (depending on your budget) and has a great no-hassle return policy if you end up ordering the wrong size.
PRO TIP: when shopping online, try to look for boots without zippers! You do not want zippers rubbing on horses and saddles as you get up and down. Get the pull-on boots.
Pros
Limitless style options
Tons of available sizes (kids sizes too)
Free shipping with Amazon Prime
Easy returns & exchanges
Purchase from multiple brands at once
Inexpensive options
Cons
Can't try on before you buy
Waiting for shipping
Too many options can be overwhelming
Fun Fact: Ariat & Justin kid's boots have a special insert they call "wiggle room" and "Room 2 Grow." When your kids' boots start feeling a little snug, you can remove this insert and free up about a half-size!
Sizing
Order half a size up! Boots usually fit better either a half or full size up. This is normally true for kids', women's, and men's sizes alike.
Kid's Boots
Brand names are great, but tiny feet grow fast. Some cheaper options are just as durable. Check the reviews & don't break the bank!
Toe Shape
Pay attention to toe shape when you're buying boots! Kids usually prefer square-toe or round-toe boots for more room by the toes.
My Favorite
I’m a sucker for Ariat boots—they’re my favorite & last a long time. My husband, on the other hand, buys whatever's on sale!
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The Takeaway
Finding horseback riding boots on Oʻahu can be more challenging than expected, especially when you’re getting ready for your first lesson or shopping for growing kids. This post walks you through the reality of buying boots on island, including what you can (and usually can’t) find at local stores like Work Shoe Hawaii and Red Wing, along with the pros and cons of each.
This post also covers why department stores like Walmart can be a quick, budget-friendly solution for youth riders, and explain why ordering online—especially through Amazon—is often the best option for selection, pricing, and kids’ sizes. For a more personal perspective, I also share personal tips on sizing, toe shape, and choosing boots that work well for lessons without overthinking it.
Personal Note: I've bought riding boots for myself, my husband, and my kids (ages 8 & 9) on Amazon. We've all bought boots in person in the past, so we've got an idea of what we like and how to order sizes. Here's a few tips from my experiences that might help you make decisions when ordering online: