Back in Fashion: The How’s and Why’s of Wearing Cowboy Boots

A cowboy riding a bullCowboys wear them all the time, especially when they are herding cattle on horseback. Their design is much more functional than a fashion statement – making sure that their wearer doesn’t fall off their horse—although they can be as stylish as they come.

For the rest of us, the only way we have ever experienced them is through Western movies where heroes and villains alike sport them in all their glory. Which is a shame, really, is that men’s cowboy boots you can buy from stores such as A.A. Callister can be as comfortable and fashionable as any dress shoe.

And contrary to popular belief, you don’t have to be a cowboy nor be in Texas to wear cowboy boots. Why, even ladies can make them an essential piece in their fall shoe collection.

Thanks to influential designers such as Raf Simons at Calvin Klein and Phoebe Philo at Celine, not to mention streetwear brand Hood by Air that reintroduced them to the catwalk. Even Givenchy’s new designer, Clare Waight Keller, donned a pair after putting them on their models first.

Why wear them?

If you have always been sneakers and dress-shoe person, you will definitely have some misgivings and a lot of questions on wearing a pair of cowboy boots. Sure, actors had worn them even when they were not in a Western movie, and Ronald Reagan had a pair on when he trod the presidential campaign trail.

For us mere mortals, Western boots would just look like typical leather shoes of high quality from a distance, but get up close and personal, and we can see why they have their unique charm.

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First, cowboy boots have a distinct and stylish taper while their heels can give the wearer an added height of from a half-inch to almost two inches. Second, they come in different decorations that will appeal to most.

They are most certainly a unique type of footwear that can help you leave a lasting impression on people.

What should you wear them with?

One thing you need to remember if you are planning to wear cowboy boots and you’re not in Texas or any American Southwest territory is that they are enough to give your outfit a western theme. So don’t overdo it that you look like someone going to a costume party.

That said, here are clothing items you can wear with your Western boots:

  • Collared shirts, including plain white dress shirts. T-shirt and blue jeans are appropriate in a country music show.
  • Dark, close-fitted jeans with a boot-cut style. And never tuck the jeans into the boots.
  • Trousers and casual suits that have roomy legs so that the boots’ shafts don’t bulge.
  • Sports jackets.
  • Leather belt with decorative buckles that are not too big and don’t have turquoise inlay.

Where should you wear them?

Keep in mind that, unless you are in Texas (or actually a Texan), cowboy boots are purely for fun social events, never for business. So you can wear them to events where they have step dancing like salsa, square and the likes.

They’ll certainly won’t be out-of-place in casual restaurants, county or state fairs, rock and country concerts, picnics with a loved one, and any activity that involves horseback riding.

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Conversely, don’t ever wear them during first dates and political events, while making a presentation or attending an upscale theater performance. They’re also not good for long hikes or drives or for modern dance clubs.

Now that you know a lot more about cowboy boots, go ahead and try on a pair. They may be harder getting used to than sneakers and dress shoes, but once you’ve grown into them, you’ll realize they are feet-friendly as well, and can actually boost your confidence.