Can You Wear Cowboy Boots With Shorts? Best Fashion Styles

Last updated: November 15, 2023

By: Miles HenryFact Checked

Picture this: it’s a hot summer day, you’re at a country music concert, and you spot the coolest fashion trend – cowboy boots with shorts. But is this look just for the stage, or can you pull it off too? Yes, you can, and it can look terrific.

Wearing cowboy boots with shorts is a fun way to mix styles, especially in the summer. For girls, this combo can be a stylish choice that shows off their personality. But for guys, it’s a bit trickier – it’s usually not seen as a good match in fashion.

I started thinking about this when my family and I were getting ready for a Garth Brooks concert. My wife and daughter chose to wear cowboy boots with their shorts and totally rocked the look. I was initially skeptical, but it was an excellent choice for a casual, country vibe. Here’s a guide on how you can make cowboy boots and shorts look great, no matter who you are.

What Types of Cowboy Boots Look Best With Shorts?

Certain combinations of cowboy boots and shorts for women go very well. Cowboy boots with fringe or embossed designs can also add a touch of style to an otherwise casual outfit. However, it is important to choose the right style of cowboy boots to complement your outfit. For example, cowboy boots with a pointy toe may not look as flattering with shorts as cowboy boots with a rounder toe.

But regardless of the style, always buy comfortable cowboy boots that fit correctly and don’t cause pain or discomfort. My wife was miserable after walking a mile just to get to the stadium to see Garth. Her feet blistered from excessive rubbing against her heels. You don’t want this happening to you.

Here is a rundown of the various types of cowboy boots you can wear with shorts:

Western Boots

This is the classic or traditional cowboy boot- the original boot. It is practical and functional and best paired with denim shorts. It also works for cotton, cargo, short booty, board, and boyfriend shorts. The choice of material and color for the shorts will depend on the color of the leather used in making the boots.

Riding Boots

As the name indicates, these cowboy boots are designed for riding. So, if you intend to use them for that, pair them with denim shorts or moisture-wicking biking shorts. Keep the ride short and avoid riding over obstacles.

However, I recommend pairing these cowboy boots with jeans for horseback riding and wearing them with casual shorts when hitting the town. They look good with just about any style of shorts.

Ropers

Ropers are generally equipped with a shorter shaft than traditional or classic cowboy boots. These boots look great with chinos, cargo shorts, capris, and denim shorts.

Buckaroo

This style of cowboy boots is versatile and stylish. It has a taller shaft than most other styles and can be paired with shorter-than-average shorts.

Stockman

The Stockman style of cowboy boots has a deeper scallop on the shaft than other cowboy boot styles. It is made of leather and often features a beautiful contrast stitching pattern on the shaft.

Work Cowboy Boots

These boots are for the hardworking cowgirl or cowboy and are often equipped with steel toes or other reinforcements to withstand rough working conditions. Work cowboy boots are non-decorative and are generally made of nylon or leather.

These go well with denim shorts, boy shorts, boyfriend shorts, booty shorts, and boxer shorts. Men can wear work cowboy boots with cargo shorts or 3/4th pants with extra pockets. They can even choose special work shorts designed for personal protection.

Different Styles of Shorts to Pair with Cowboy Boots

Most of these styles of shorts work best for women looking to wear cowboy boots with them:

• Booty shorts are the shortest style of women’s shorts – almost like underwear. Knee-high cowboy boots like westerns, buckaroos, and work cowboy boots can go well with this style.
• Boy shorts are slightly bigger than booty shorts and have a high-rise waist. It can go well with ropers, buckaroos, work boots, riding boots, etc.
• Cargo/combat shorts – these are loose and baggy with multiple pockets. They look good with Ropers, Stockmans, and other cowboy boot styles having shorter shafts.
• Denim cutoffs can go well with any cowboy boot style- ropers, buckaroos, dress boots, work boots, traditional cowboy boots, etc.
• Pedal pushers – this style of shorts ends 2 inches above the knees. It goes well with western, Ropers, Stockmans, etc.

How to Style Shorts with Cowboy Boots?

The following ideas are for women looking to style their cowboy boots with shorts.

• Jean-shorts or denim shorts with western or cowboy boots are a classic combo. You can wear a short top, a knotted blouse, or a tube top with shorts for summer. Wear a jacket or blazer in winter to keep warm and look classy.
• A button-down shirt with shorts and knee-high boots is ideal for a casual, relaxed look. To add pizzazz to the look, only tuck one side of the shirt in the shorts.
• High-waisted shorts with a tailored fit with a smart blazer over a cami top will give you an elegant look.
• Shorts with a belt, a sleeveless top tucked in the shorts, and chunky cowboy boots will make you look like a fashion diva.
• For an effortless look, wear shorts and a shirt/top of the same color and break the monotony with a contrasting belt and cowboy boots the same color as the belt.

Below is a YouTube video showing some favorite cowboy boot styles.

4 Reasons Why Men Should Not Wear Cowboy Boots with Shorts

Undoubtedly, cowboy boots are an indispensable part of men’s fashion. They are a true representation of American culture and heritage. Everyone can wear cowboy boots irrespective of age, but pairing them with the proper attire can be difficult.

For men. Cowboy boots are an authentic symbol of old-west cowboys. Their traditional design features a boot that hits mid-calf or higher on your leg and has a sturdy heel, perfect for horse riding. Shorts, however, provide little protection when in a saddle.

As such, we recommend wearing cowboy boots with jeans. Not only are shorts impractical, but they also make men’s legs look scrawny when paired with cowboy boots. Here are some additional reasons for me to avoid shorts and cowboy boots:

1. It’s Traditionally Unacceptable

Cowboy boots and jeans are like PB and J or Mac and Cheese. They are fashion statements and simply go well together. But shorts and cowboy boots are out of the question.

Check out photos of authentic cowboys; chances are you will only find ones wearing cowboy boots with jeans; rarely will you see them in shorts with boots.

Tradition also dictates that cowboy boots should only be paired with jeans. It is believed that real cowboys started wearing (Levi’s) jeans in the 1870s, and since then, boots and jeans have been the attire for ranchers and cowboys.

2. It gives a Disproportionate Look.

Shorts with cowboy boots are just not the right combination because of the disproportionate nature and shape of both items. 

Cowboy boots are usually bulky. On the other hand, men’s shorts are usually baggy, and when paired with bulky cowboy boots, they give the wearer a disproportionate look.

On the other hand, Jeans are form-fitting on the upper side with space on the bottom that accommodates the cowboy boot’s tall shaft. Some jeans also allow stacking to show off the boots in style.

3. The Combo Could Make Your Legs Look Skinnier

Shorts end at the knees (or above), drawing attention to the wearers’ legs. If you wear cowboy boots with shorts, the combination is bound to make your legs look scrawnier. 

This combo works well for women since shorts enhance their curves while the boots make their legs look longer, their bodies leaner, and overall they look a lot taller. For men, it just ends up making them look weird and skinny.

4. It Isn’t The Choice of The Fashion-Conscious Man

Well, let’s put it bluntly. The combination of shorts and cowboy boots is best left to eccentric or weird men. A fashion-conscious or fashion-forward male will never wear this combination. 

As mentioned earlier, combining shorts with Western boots will make the individual look rather disproportionate. It is a combo that no self-respecting man would choose. The unusual combo will surely draw attention to the man, not in a good way. It would make one look less macho and draw out his flaws, like skinny legs.

If you care about making the right style statement, you would never wear shorts with cowboy boots.

Do Cowboys Ever Wear Shorts?

A few of my hard-core cowboy friends never wear shorts. So I was curious how they would dress for a swimming party. Well, one showed up wearing shorts, and the other two wore jeans.

Cowboys generally prefer to stick to their jeans, but there’s no reason they can’t enjoy the comfort of shorts on a hot day. Here are some other times you may find a cowboy in shorts:

1. Under Certain Weather Conditions

An unexpected downpour might force a cowboy to wear shorts. He can wear cowboy boots with shorts as their longer shaft protects his legs from the muck.  Shorts not only keep the mud off but can also keep one cool if the weather becomes humid after the rain. 

Shorts with cowboy boots are also okay for cowboys to wear in extreme heat when jeans make the legs uncomfortable and sweaty. In this case, a cowboy might even ride in shorts, but only over a short distance and when there are not too many obstacles around.

2. For Work

Cowboys often have to work under grueling conditions. Shorts made for work, such as cargo shorts, heavy work shorts, three-fourth pants, etc., allow freedom of movement and flexibility while working with animals.

I often work around the barn wearing my Ariat Workhogs with cargo shorts. In Louisiana, we often have scorching and humid conditions. You can easily get overheated wearing heavy denim jeans.

However, I still want to protect my feet from snake bites and a young horse’s inadvertent stepping on my toes. Shorts and cowboy boots allow me the flexibility to bend, climb, squat, etc., as required for the job, along with adequate foot protection.

3. When Riding for Short Distances

I never plan on riding horses in shorts, but there are occasions when I’ve hopped on horses in shorts to correct a problem or show an inexperienced rider something they need to work on. Sometimes, riding in shorts is okay, but it is best to wear jeans for longer rides.

Should You Wear Socks with Cowboy Boots?

Traditionally, cowboys do not wear socks with cowboy boots. However, if you want extra comfort or plan on wearing the boots all day, you could wear some socks. Socks are a must-have in winter to keep your legs and feet warm under the boots. Furthermore, they are a necessity in summer to absorb sweat.

If your cowboy boots are new, pinch, or cause blisters, socks can be useful, especially during the breaking-in period. Later, once your feet are comfortable in the boots, you can stop wearing socks if needed.

4 Tips on How to Take Care of Your Cowboy Boots So They Last Longer

While cowboy boots are designed to be tough and durable, they still require some care and maintenance to keep them looking their best. Here are a few tips on how to take care of your cowboy boots:

1. Wipe them After Every Use – Always wipe your cowboy boots with a damp cloth, an old sock, or a soft rag after every use.
2. Polish and Buff Regularly – For genuine leather boots, use cream leather polish like this one to keep the boots looking brand new. You can polish and buff after every 3rd use. Ideally, you should clean them with a little saddle soap and tepid water after every use. Make sure you hand-dry them with a soft cloth afterward. Never set a pair of wet cowboy boots by a heat source or open fire.
3. Use a Conditioner – After the boots are dry, use a neutral or compatible conditioner to keep the leather from becoming dry, brittle, and cracked. Avoid sticky, gooey waterproofing products. When in doubt, ask the manufacturer for recommendations for products for conditioning your leather cowboy boots.
4. Treat Nicks Right Away – You can use a swab and a matching-colored cream conditioner, then buffing and polishing.

Conclusion – Can You Wear Cowboy Boots With Shorts?

At first glance, cowboy boots and shorts may not seem like a natural pairing. After all, cowboy boots are often associated with more formal occasions, while shorts are typically considered casual wear. However, there are no hard-and-fast rules regarding fashion, and cowboy boots can look great with shorts.

The key is to choose the right style of cowboy boots and pair it with the right type of shorts. For example, a classic cowboy boot with a pointed toe would look out of place with denim cutoffs. However, a more relaxed cowboy boot with a rounded toe would be a perfect match.

Similarly, a pair of khaki shorts would look great with cowboy boots, but leather shorts would be too edgy. With trial and error, you can find the perfect combination for your style.

Note: Men should not pair cowboy boots with shorts. This isn’t the traditional combo, and genuine cowboys avoid it. Cowboy boots are best paired with jeans. Shorts with cowboy boots make the legs look scrawny and create a disproportionate look.