How To Wear Cowboy Boots Without Looking Country

By Kato Watson, 04 Jul 2020

When we talk about fashion and function, cowboy boots immediately come to mind. After all, these up-to-the-minute trendy shoes are more than just simple boots.

They are classic pieces of footwear that boast a rich history of working with cowboy boots centuries ago.

I personally love cowboy boots. When worn well, they bring out the trim, sleek look in you. The take-home part of my sentence is ‘’when worn well.’’

So how do you wear cowboy boots without making a big ass of yourself? Good question.

Cowboy boots look best when worn with slim boot cut jeans or pants that are neither too long nor too short. They complement gray, black or brown jeans or slacks.

As for where to wear cowboy boots? Please for the love of God, don’t think you’d have to attend a Ray Cyrus Concert for you to rock your cowboy companions.

No, you can wear your cowboy boots to bars, weddings, county fairs, rock concerts and even romantic outings.  

So, if you’re looking to add cowboy boots into your wardrobe, but aren’t sure how to pull them off or what to pair them up with, you’re in the right place.

The goal of our article today is to help that man who has been wanting to rock cowboy boots but isn’t sure how to do that.

Let’s delve in, shall we?

A Short History of Cowboy Boots

You’ve seen cowboy boots in all Western themed movies - but what’s the real story behind them? Of course, they are more than just an aesthetic choice. In their original form, cowboy boots were a lifesaver for working men.

Way back in time, Cowboys needed practical, affordable footwear that they could use while working. The original boots served this purpose. They allowed them to ride and walk back to back with equal support and comfort.

Cowboy boots were specifically made for work, but there were also fancier options designed for off the job occasions and events.

The Functional Side: Why Wear Cowboy Boots?

I know it’s hard to find a reason to wear cowboy boots because most people see them as novelty pieces worn when riding a horse or when attending specific occasions only.

The savvy gentleman, though, understands the importance of wearing cowboy boots and uses them as an instant attention-seeking item to get tongues wagging. If you spot a leather shoe from a distance, you wouldn’t be too interested, until you get closer and realize that it’s a flashy cowboy boot which can’t simply be ignored thanks to its embroidered upper design, heel height and sharp pointed toe.

So, without further ado, here are 3 reasons you should wear cowboy boots.

1. Cowboy Boots are Rich in History

Cowboy boots aren’t just an attention-seeking piece for bold men, they have an intriguing history behind them, especially in the era when horses were the only mode of transport.

At that time, cowboy boots were worn for one specific reason - to protect horsemen while riding. For instance, cowboy boots don’t have laces so that in the event the Cowboy fell from the horse, they wouldn’t get caught up.

Rocking cowboy boots now is one way to truly appreciate the living history of these boots.

2. Cowboy Boots Are Stylish and Elegant

The best thing about cowboy boots is that they give you instant style without having to try too much. You can pair them with a simple collar shirt and jeans, and the boots will still turn heads.

The main reason behind this is that cowboy boots have an undeniable flair to them. Their height, heel length and shape of toe make them the center of attention.

Without doubt, these classic footwear is for men who aren’t afraid to flaunt their style anywhere.

3. Cowboy Boots Ooze Confidence

Cowboy boots are famous for being attention-catching. With different colors, materials and finishes, they are nothing but elegant masterpieces. Any man who wants to successfully rock cowboy boots should wear them with a lot of confidence.

If you’re a bit wary about how you look in cowboy boots, it will definitely show in your posture and body language, and this won’t go in your favor as far as confidence is concerned.

So, wear the boots like you mean it because people will be looking.

We’ve seen why you should wear cowboy boots, let’s now move to the main features of a cowboy boot.

Understand Main Features of a Cowboy Boot

Uniquely Designed Toe Shape: Most cowboy boots have toes that are wickedly pointed. However, thanks to modernization, many manufacturers are now incorporating tapered toes to fit a wider range of everyday outfits.

Height: Most cowboy boots go well above the ankles. Shorter men are really lucky in this regard because it gives them the illusion of height. The heel alone, which is usually not less than 2 inches, adds a lot of height to the shoe.

Stylistic Stitching: There are very few plain cowboy boots on the market. Most of them come with stylistic decorations and stitching. The shaft is where most of these designs are usually located. They add a lot of style to your outfit.

What to Wear with Cowboy Boots

A good rule of thumb is to wear one Western style piece per outfit, and nothing more. So, if you’re wearing cowboy boots, pair them up with a simple leather belt and jacket, and not another cowboy hat or bolo tie unless you really want to look country.

You don’t want to look like you’re dressing up for a costume party. Your outfit should be well thought out and make sense. In other words, just stick to a relaxed jacket and simple trousers whenever you’re wearing cowboy boots.

What Tops to Pair with Cowboy Boots

Collared Shirts: A collar shirt is the best top to wear with cowboy boots. It perfectly pairs with jeans and even dress trousers. Dress shirts with one solid color are the best. Casual shirts with plaid are also perfect.

T-shirts: If you want a more relaxed look, a solid color tee-shirt will do. Don’t do tee-shirts with brand names.

Denim Jackets:  Denim jackets always look nice when paired with cowboy boots. I would almost tell you to never wear cowboy boots without a nice-looking jacket. It balances out the western look in a way that a shirt alone just can’t

Sport Coats: Sport coats will instantly transform your style from cool to dapper. Even with a simple colored shirt inside, a sport coat adds a lot of elegance to your overall outfit.

What Pants to Pair with Cowboy Boots

Jeans: You can never go wrong with a pair of jeans. They should be dark and fitting, and not the typical work jeans in color blue. A boot-cut style is preferred. But again, never tuck your jeans into the boot unless you’re riding a horse and it calls for it.

Dress Trousers: Cowboy boots and dress trousers go well together, especially if you’re going for a Western-themed event. A casual suit also always looks great in cowboy boots.

Khakis: Just like denims, khakis are great for a casual look. They blend so well with cowboy boots for almost any occasion, and the best part is you’ll have so many colors to choose from.

What Accessories to Pair with Cowboy Boots

Belt: Belts with fancy buckles or leather are always the best accessories to pair with a cowboy boot. You don’t need a belt with all the bells and whistles including rattlesnake skin or silver buckles, but a subtle decoration will go a long way in accentuating your Western style.

Hats: Hats are not necessary; but if you really want to look country, then a nice Western style hat will do the trick. If you want people to instantly go "cowboy’’ when they look at you, then a Western style hat is a must-have accessory.

Spurs: If you are not about to ride a horse, please don’t do spurs on your boots.

In short, you want to dress in a way that people can acknowledge your cowboy boots without them (the boots) necessarily being the center of attention.

We are going for that comfortable, relaxed, cool vibe - all of the things that go hand in hand with Cowboy and Western styles. If you are strolling around the city, you may want to look a lot dressier than a cowboy going on a rodeo.

For the perfect cowboy outfit from head to toe, try a pair of dark jeans (not blue jeans), a plain colored shirt (one color), a solid colored jacket (we recommend gray), and of course a casual cut. You can add a fancy belt and you’ll be looking all stylish, confident and Cowboy.

Where to Wear Cowboy Boots

By now, you already know that Cowboy boots are casual attire. They are not formal clothing, and should not be worn to business events, unless the business involves horses.

We recommend wearing cowboy boots to casual events like weddings. In short, places that are light-hearted and have some machismo and panache so that you won’t be out of place.

Here are some places where it’s okay for you to wear cowboy boots:

  • Dancing arenas- square dancing, salsa dancing, etc.
  • Bars
  • County and state fairs
  • Country and rock concerts
  • Romantic outings with friends and loved ones
  • Comedy events
  • Any events where there are horses

Where Not to Wear Cowboy Boots

Places you should never wear cowboy boots, unless you really want to get people talking, include:

  • Political events (might send wrong message)
  • Hikes and long drives (extremely uncomfortable)
  • Theater functions (not appropriate)
  • Date with a loved one (will definitely raise eyebrows)
  • Modern clubs (wrong style)

There you have it - all that we got on how to wear cowboy boots. We hope you’ll be a lot more inclined to try out this fashionable footwear.

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