Interested in getting a pair of cowboy boots but need help figuring out where to start? In this guide, I’ll explain what you need to know.
I recently moved to a Western ranching town. While it was a rarity to see cowboy boots in the wild back at home on the East Coast, here they’re ubiquitous.
The other day one of my friends told me that, “There are two days that matter in the life of a man. The day he gets married, and the day he gets his first pair of boots”.
While this may or may not be true for you, the world of cowboy boots can be an intimidating one to enter. It can be hard to know where to start, why there are so many different types, and which is right for you.
And then there is the question that burns in the mind of anyone researching their first boot purchase:
“Do I have to be a cowboy to wear cowboy boots?”
Well, let’s dive in and answer that and all the other questions.
History of Cowboy Boots
Cowboy boots trace their origins in the United States back to the 1800s. They were influenced by a vaquero-style boot worn in Spain since the 1600s.
The cowboy boot was originally made for people who worked with horses to provide them with a more comfortable and controlling ride. The tall boots would protect the calf and leg from brush and plants, while the thick heel made the boot fit securely into the stirrups.
Because of how sturdy the boots were, men began using them for work purposes outside of just riding.
After the American Civil War, many veterans moved out West and pursued working with cattle and on farms. They traded in their military boots for cowboy boots, as they had similar durability and strength.
In the 1940s, as Western movies became bigger and more common, cowboy boots surged in popularity. John Wayne, Clint Eastwood, and mass production are the culprits for making the boot the Western staple that they are today.
Cowboy Boot Anatomy
A cowboy boot is comprised of a few different parts:
Shaft
The shaft is the part of the boot that rises up on the calve. It can go up to the knee, just past the ankle, or anywhere in between.
There are usually stitchings in the shaft that help give the boot its classic look. These stitchings also help keep the shaft stiff so it doesn’t bend and roll as it ages.
Pull Strap
Located at the top of the shaft, the pull straps make it easier to pull the boot on.
Heel
The back portion of the boot rests right under the heel of your foot. The heel can vary greatly in thickness depending on each boot.
They were originally raised to prevent the boot from sliding forward when in a stirrup and gave a higher sense of control. However, if that is not a concern of yours, they can also help give you a bit more height to impress that special someone.
Vamp
The vamp is located on top of the boot and covers the top of your foot. There is usually a stitching or design here. When the legs of your pants are worn over the boot (which we’ll touch on later, but if you are a man it is a must), then the only part of the boot that shows is the vamp.
Insole
The insole is where your foot rests on the inside of your boot. This is what you’re standing on, so it must be comfortable.
Midsole
The midsole is between the insole and the ground, which provides support and holds the boot together.
Outsole
The outsole is what keeps you from walking barefoot on the ground. In other words, it’s the outermost layer on the bottom of your shoes or boots.
6 Different Styles of Cowboy Boots
Which boots you should buy depends a lot on what you plan on doing in them.
There are six main styles that you should consider.
Western Boots
Yeehaw, these are your good ol’ traditional boots. These are made for riding horses.
The pointed toe makes it easy to slip into the stirrups, the heel keeps it locked there, and the shaft keeps your leg protected as you ride.
Roper Boots
Roper boots are similar to Western boots but are more geared towards, you guessed it, roping cattle.
The difference is they are a bit more comfortable, with a lower shaft and heel making it easier to wear them for long stretches of walking.
Work Boots
These boots are made for hard work. With a thick and grippy outsole, these were made for construction sites, warehouses, and any other workplace.
They are a great substitute for traditional work boots. Many are equipped with steel toe reinforcement.
Dress Boots
Dress boots are boots that have more emphasis on style over performance. They can be made of higher quality leather, and usually have more intricate designs and stitchings.
You can easily wear them to weddings, church services, or even just a night out on the town.
Exotic Boots
These are boots that will turn heads. They are made out of uncommon materials such as alligator skin, ostrich leather, snake skin, and many others.
These are usually only seen on very formal occasions or on the feet of show-off city slickers.
Short Cowboy Boots
Short boots have a shorter shaft that ends around the ankle.
They are easier to take on and off and are lighter than traditional boots. In my opinion, these should be exclusively reserved for women’s Western wear. As a man, you should refrain from this short-shafted copout.
Instead, if you are interested in short slip-on boots, check out Chelsea boots.
Can Anyone Wear Cowboy Boots?
YES! Anyone can wear cowboy boots! You don’t have to know how to ride horses and you certainly don’t have to work on a ranch.
They are simply another type of footwear that brings your style to the next level.
3 Different Ways to Wear Cowboy Boots
If you want to wear cowboy boots, you do not have to dress up in full cowboy apparel and adopt a cheap fake accent. There are many different ways to wear cowboy boots outside of the Western style.
In all of these styles, you will have to wear them with boot-cut jeans or pants — pants that are cut wider at the bottom so that the pants can go over the boots.
Cowboy Boots for Work
Many work boots have steel-toe reinforcement, which could be a must if you are looking to bring these to a construction site.
Steel-toed cowboy boots are very commonly found in most job sites in the US. So don’t be afraid to swap out your Timberlands for some Ariats.
Casual Wear
You don’t need a “‘reason” to wear boots, you can simply replace your normal daily footwear with a pair of boots. School, shopping, and your nephew’s basketball game are all completely acceptable places to wear boots casually
Pair the boots and jeans with a flannel, a sweater, or even a t-shirt. It’s hard to go wrong when wearing boots casually, don’t overthink it. For the most part, just avoid wearing them with shorts, sweatpants, or anything John Wayne wouldn’t wear.
Cowboy Boots with a Suit
Wearing boots with a suit is a great way to show your personality when dressing up.
While I truly believe anyone can wear cowboy boots, but not anyone can pull them off with a suit.
If you live in the Western US, own a ranch, or regularly wear cowboy hats, go for it. If you’re more likely to pull up to a Starbucks than you are to a rodeo, you might want to think again.
Cowboy boots with business wear is a bold look. Just like with wearing any other unusual accessory, it’s best if they are part of your story.
For example, the bishop (i.e. pastor) of my church wears cowboy boots with a suit, white shirt, and tie every Sunday. His boots are clean and polished.
Like I said, I live in a Western farming community, and he’s a cattleman by trade — so cowboy boots are a natural fit.
However, if you live in central London and work in the finance industry, cowboy boots are going to look completely out of place. Instead, you’ll need a pair of quality black (not brown) dress shoes (preferably Oxfords). The suit and accessories may be the same, but the situation is different.
If you really want to play up the Western look you could throw on a cowboy hat and a bolo tie with your cowboy boots. However, outside of small towns and traditional Western events, I’d probably wear a traditional tie and leave the hat at home. The idea is that you want to avoid looking costumey.
How to Size Cowboy Boots
A proper fit is essential to enjoying your new boots to their full potential. Here is a great resource from Ariat Boots for choosing the right size cowboy boots.
While tons of online retailers sell boots, trying them on is the only way to know if they fit. When you put on a boot that fits well, you will hear a very faint “pop” as your heel clicks into place.
Once you feel that pop, gently stand on your toes and see how much your heel lifts up. You want it to rise slightly. A standard heel lift is ⅛”.
You should be able to fit a thumb between your toe and the end of the shoe. The widest part of your foot is at the balls of your feet, so that should sync up with the widest part of the boot.
Make sure that the boot isn’t too narrow for your foot, you want it to be secure but comfortable.
5 Good Cowboy Boot Options
There are so many great options for your first pair of boots, and you won’t really know what you like until you try a pair. Here are some top brands to consider:
Ariat
Talking to my Western friends, one of their favorite brands is Ariat. One pal reports, “They’re the perfect blend of comfort, durability, and performance.”
He highly recommends the Ariat Sport Strattens, which he says are the most comfortable footwear that he owns.
Justin Boots
A classic brand that has been at the top of the industry since 1879, Justin Boots can take on the toughest of conditions and jobs.
A great option if you are looking to get your boots dirty, and one of the most reasonably priced boot brands.
Georgia
A tough and durable boot, Georgia boots are another great option for hard workers.
They are a classic brand and look, and can take on any job.
Lucchese
If you are looking for a stylish boot and money is less of an issue, then Lucchese is the brand for you.
Worn by celebrities and people around the world, these boots always stand out.
Frye
Frye is the oldest boot company in the United States and ironically produces the most modern-styled boots.
If you want something that looks sleek and has less of the classic “cowboy boot” look, then this could be your option.
FAQs
Here are answers to some common questions about cowboy boots.
Do I tuck my jeans into my boots?
No, don’t tuck-in your pants into your boots! Unless there is a need to keep the bottom of your jeans clean during work, then there is no reason to tuck them in.
What pants do I wear with my boots?
Bootcut jeans or cowboy-cut jeans are most commonly worn with cowboy boots. You can also wear work pants, like Dickies, chinos, and even in some cases more formal trousers.
For jeans, you ideally want to buy them longer than other jeans because they will cover the shaft of your boot and rest and the top of your foot. For example, if you typically wear 32L jeans, you might want to try on pairs that are 34L to 36L.
How much should I spend on my first pair of boots?
A good price point for your first pair of boots is $100-$300. I would be very wary about buying any cowboy boots under $100 dollars. It’s worth paying a bit more for higher-quality leather and craftsmanship that will last longer.
Final Thoughts: They’re Not Just for Rodeos
Everyone can wear cowboy boots, they can work with so many outfits and are surging in popularity.
If you are still wary about buying your first pair of boots, then take this advice from the most famous cowboy of all, John Wayne:
“Courage is being scared to death, but saddling up anyway.”
Take some courage and go for those new shiny boots.
If you have questions or comments leave them below!
