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Can You Wear Cowboy Boots With Shorts? (Men’s Guide)

December 22, 2022
Can You Wear Cowboy Boots With Shorts? (Men’s Guide)

Cowboy boots are a globally iconic item of men’s fashion. They’re easily recognizable and can look great, but can be tough to successfully pair with other clothes. So, can men wear cowboy boots with shorts?

Men generally should avoid wearing cowboy boots with shorts. It can appear overly eccentric and make your legs look scrawny. It also goes against the traditional use of cowboy boots and can look disproportionate.

While it’s a popular combination with women, it’s rarely ever worn by men. 

That’s the gist, there’s much more to it.

So, let’s dig deeper.

can you wear cowboy boots with shorts
Image From Deposit Photos

3 Reasons Why You Shouldn’t Wear Cowboy Boots With Shorts

Cowboy boots with shorts is a pretty controversial combo. Here are some reasons why you should avoid wearing cowboy boots with shorts. 

1. It Makes Your Legs Look Excessively Scrawny

Wearing shorts with cowboy boots can make legs look skinnier than they are due to the disproportionate nature of the garments together.

Typically, cowboy boots are pretty bulky. When wearing cowboy boots with shorts, it exposes your legs, directly comparing them to the bulkiness of your boots.

Furthermore, shorts can often be pretty baggy.

So when you’re wearing shorts with cowboy boots, the contrast between the bulk of your garments and your legs can make them appear skinny in comparison. 

When wearing cowboy boots with shorts, the illusion of skinny legs can make you appear less masculine.

2. You Can Look Eccentric

Looking eccentric is something most men actively avoid. When wearing cowboy boots with shorts, you risk looking eccentric.

This is for a couple of reasons. Firstly, as mentioned, the clothing looking out of proportion to the legs can draw unwanted attention. 

On top of this, the combination in itself is incredibly unusual and, therefore, stands out like a sore thumb. 

Cowboy boots are typically worn in the fall and winter due to their ruggedness and ability to withstand terrain and weather.

Shorts, on the other hand, are pretty much exclusively summer-oriented. This kind of contrast doesn’t usually look good in men’s style, and this is no exception.

This means that wearing them together can look flamboyant and demonstrate a lack of awareness of the basics of men’s style. 

3. It Goes Against Tradition

Historically, cowboy boots were worn when riding a horse to maximize protection while still being comfortable.

The tall shaft of cowboy boots was designed to protect your legs from water, shaft, the elements, and other potential hazards while atop a horse.

Cowboy boots also have a distinctive heel, originally to aid the security of the boots in the stirrups.

Wearing shorts with cowboy boots would somewhat defeat the purpose of having protective boots, as your legs would still be exposed.

This is why cowboy boots are traditionally always worn with trousers and how, by wearing shorts, you’re going against a centuries-old tradition.

2 Exceptions When Wearing Cowboy Boots With Shorts Might Be OK

While, typically, you should avoid wearing cowboy boots with shorts, there are some exceptions when wearing this combination might be acceptable.

1. It Has Been Raining

Sometimes, the weather seems to change in the blink of an eye – from heavy rain to sunny spells.

In this case, it may be acceptable to wear cowboy boots with shorts. 

Cowboy boots are particularly good at protecting your feet and lower legs against the elements – water included.

When it has been raining and the ground outside is wet and muddy, but the weather has since cleared up, and it’s warm, cowboy boots are a fantastic option.

However, to keep cool, shorts may be necessary. In this case, wearing cowboy boots with shorts may be appropriate or even preferred.

Having said this, usually, in warmer weather, you’re better off going for something more standard, such as sneakers, sandals, espadrilles, or boat shoes. 

2. You’re Working In Particular Conditions

Utility often comes before appearance in the workplace. This is particularly true if you’re working with animals.

Cowboy boots are traditionally made for work with horses. And while they are typically worn with pants, it isn’t always the case.

If you’re working with horses and it’s particularly hot, for example, cowboy boots might be your shoes of choice.

However, shorts may be a necessity to keep cool while working. In this instance, it’s acceptable, and arguably optimal, to wear cowboy boots with shorts.

Other examples of occupations that may favor cowboy boots over typical shoes are farmers, laborers, and construction workers.

While the heel of the cowboy boots may pose a problem for some people, they are generally suitable for these jobs.

Shorts are always acceptable with cowboy boots if you’re in a situation prioritizing utility and function over appearance.

3 Tips For Wearing Cowboy Boots With Shorts (If You Must)

Here are 3 tips for wearing cowboy boots with shorts. While it isn’t advised, sometimes it may be necessary. 

1. Brown Cowboy Boots Work Best

Traditionally, all cowboy boots are made of leather and are, therefore, brown in color with a worn appearance from work.

It’s best to keep this tradition alive when wearing cowboy boots with shorts. 

Brown leather looks better with age and use. Because your cowboy boots are likely going to be used for rough work, terrain, and weather, brown ones work best.

Furthermore, brown boots are much more common than boots of other colors, such as black, and are, therefore, often cheaper.

On top of this, brown cowboy boots are arguably more versatile than boots of other colors.

This means that you have a wider variety of shorts choices and can, therefore, make your cowboy boots with shorts look less awkward.

2. Stick To Cargo Shorts

When wearing cowboy boots with shorts, it’s likely for utility purposes. This means that cargo shorts are your best bet for pulling off this look.

Not only do standard cargo shorts provide solid utility, but they also look the best with cowboy boots.

Their many pockets and tough fabric means that they are a great option for scenarios when wearing cowboy boots with shorts is acceptable.

On top of that, their ruggedness matches that of the cowboy boots, meaning that there is natural synchronicity in the garments.

Cargo shorts typically come in khaki or beige, and these are the colors that match best with traditional brown cowboy boots.

Wearing a canvas belt can further contribute to the robust appearance and is a great way to keep your shorts up – particularly during laborious work.

You should choose a canvas belt over a leather belt as leather belts are typically associated with more formal attire.

Cowboy boots with shorts is certainly not a formal outfit and should, therefore, not be treated as such.

Canvas belts are much more informal than leather belts and add to the rugged masculinity of the outfit.

3. Avoid “Dress” Cowboy Boots

Dress cowboy boots stray from traditional cowboy boots in that they have a much more formal edge to them.

It’s best to avoid these when wearing cowboy boots with shorts. 

Nothing about this outfit is inherently formal; shorts aren’t formal, and neither are cowboy boots. 

In fact, it’s advised to completely avoid shorts on pretty much every formal occasion.

Dress cowboy boots are suitable for some formal outfits when dressed correctly; however, this outfit is not formal in the slightest.

Not only that, but dress cowboy boots typically have some additional detail and decoration to distinguish them from standard cowboy boots. 

Under the exceptions when wearing cowboy boots with shorts is appropriate, this extra decoration would likely be damaged.

Therefore, overall, if you must wear cowboy boots with shorts, you should avoid wearing dress cowboy boots. Instead, stick to traditional cowboy boots.


You now know why you should generally avoid wearing cowboy boots with shorts, but also some exceptions when it might be acceptable. 

Remember, if you must wear this combination, brown cowboy boots, and cargo shorts work best. Also, avoid dress cowboy boots, as these are too formal.