How to wear cowboy boots: 7 ways to style these country classics

You don’t have to love country music to wear this classic style - here’s how to wear cowboy boots

How to wear cowboy boots
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Wondering how to wear cowboy boots? As the perfect transitional footwear, they pretty much go with everything and work just as well with cut-off shorts, as they do your favorite dress.

Originally created as protection for cowboys while riding their horses, cowboy boots soon became more than just an essential work item. Since then, everyone worth their fashion salt have been spotted in them, showing how to wear cowboy boots in multiple different ways. From Princess Diana matching hers with a blazer to the queen of country, Dolly Parton, wearing them with, just about everything. One of the biggest fall winter shoe trends 2022, today’s love affair with the cowboy boot stems partly from the resurgence of Y2K fashion, with designers such as Louis Vuitton, Alexander McQueen and Isabel Marant sharing their take in the shoe trends 2022, breathing new life into the fashion classic. 

For Texas-born fashion designer and CEO of Buddy Love, Grayson DiFonzo, believes comfort and cool are the reasons cowboy boots are popular once more.

“We've seen the preppy trends and '90s trends make a comeback and now the Western trends are mainstream again,” she says. (And) “With the Yellowstone show becoming such a hit, I think it really launched everyone’s fantasies to look more like Rip and Beth. Cowboy boots are also such a comfortable way to look dressy with minimal effort.”

Kylie Minogue, Princess Diana and Gwen Stefani show how to wear cowboy boots

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How to wear cowboy boots in 2022 for maximum style

If you’ve been wondering how cowboy boots are supposed to be worn in 2022, the answer is essentially, however you like. Gone are the days when they were only appropriate with double denim - these work boots are now firm fashion favorites and go with everything in your closet. And thanks to the wide variety of styles available, there’s a cowboy boot available for pretty much every style occasion.

As Grayson says: “Cowboy boots are not just for concerts and rural recreation anymore. Add them to your everyday wardrobe for a fun, trendy look that will turn heads!”

How to wear cowboy boots with dresses

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1. How to wear cowboy boots with dresses

What is boho style without a boot, especially a cowboy boot? A floaty maxi or midi dress teamed with the best cowboy boots immediately gives a cool, bohemian feel, especially if you choose a boot with embellishments or fringing. While not an obvious warm weather choice, cowboy boots look great with pretty summery frocks. The best summer dresses to choose are slip dresses and those with prairie details, as the mix of androgynous boot and feminine finishes works nicely together. While the nature of the cowboy boot injects a touch of casual into any outfit, they can also be the perfect accompaniment to a glam dress for a night out.

Styling tip: When dressing for a night out, ditch boring black and choose a metallic pair of cowboy boots and team with a short velvet or embellished dress for maximum impact. Grayson says she particularly favors a tall dress boot for evening attire.

how to wear cowboy boots with jeans

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2. How to wear cowboy boots with jeans

An obvious way to wear cowboy boots is over your best skinny jeans, as the slim-line fit means they look neat and tidy. For a smart casual outfit idea, try jeans tucked into tall cowboy boots paired with a blazer or shirt, this works brilliantly, especially if you keep it all tonal.

But when it comes to the best jeans to wear with cowboy boots, skinny jeans aren’t the only denim shape to wear with cowboy boots though. As the love of the skinny jean dwindles, look to baggier silhouettes tucked into your boots for a new twist on the trend. If opting for this look, keep the top half more fitted to contour your shape.

It’s also fun to play around with different lengths of jeans. Try a cropped straight jean with an ankle cowboy boot, or play around with how to style flared jeans in an extra longer length so that your cowboy boots just poke out from underneath.

Styling tip: If you want your legs to look longer, match the color of your jeans with your boots.

How to wear cowboy boots with skirts

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3. How to wear cowboy boots with skirts

While a denim skirt and shirt make the perfect accompaniment to cowboy boots, don’t dismiss the other skirts in your wardrobe. The masculine feel of the boot makes for a cute contrast with super feminine skirts such as those with ruffles or florals. If you’re looking for long skirt outfit ideas, cowboy boots are also the perfect finishing touch (draw inspiration from the flared jean styling tips above). 

To nail how to wear cowboy boots with skirts, try pairing an A-line skirt with a more fitted top half, finished off with knee-high cowboy boots. The best shirts for this look will be slightly more casual or with cute styling details, such as statement collars or embellishment, playing on that mix of femininity and androgyny once again. 

Styling tip: Cowboy boots will work with all lengths of skirt so don't be afraid to play around. Mix micro minis with knee high cowboy boots and maxi skirts with ankle style cowboy boots for a directional look.

how to style cowboy boots with a blazer

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4. How to wear cowboy boots with a Blazer

If you’re wondering whether you should ever wear a blazer with cowboy boots, according to Grayson the answer is a resounding yes. “A blazer, bodysuit, and cowboy boot are literally the definition of Western chic,” she says.

So, how to style a blazer with this classic country and western footwear? Take a leaf out of Emily Ratajkowski’s style book and go oversized with the blazer, add some leggings or straight legged jeans, tucking them into a pair of tall cowboy boots. It’s a look that will take you from grocery shopping to brunch with the girls. Oh-so flattering, it's comprised of wardrobe essentials you probably already have.

Styling tip: A dress, blazer and cowboy boots can definitely be smart enough for the office - just keep everything monochromatic for added polish.

how to wear cowboy boots with a blouse

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5. How to wear cowboy boots with a Blouse

Cowboy boots are a great pairing for a blouse - whether you choose a voluminous design, a longer length version or something cropped. When you’re wondering what to wear with black jeans, an easy but stylish choice is a simple white blouse, jeans and black cowboy boots - either with the jean leg tucked in or have your boots peeking out from under the hem. 

Of course, you can also play around with this look. Team a blouse with shorts and cute colored boots or add a blouse to a formal suit and tuck the trousers into your boots to get ready for fall.

Styling tip: Match the color of your boots to your blouse for a smarter finish.

how to wear cowboy boots with coords and suits shown on three women

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6. How to wear cowboy boots with a Co-ord

If you want to make a formal co-ord, such as a skirt suit, more laidback, cowboy boots are your friend. Whether tucked into suit trousers or teamed with a tailored skirt, choose boots in a similar shade to your co-ord to keep the outfit tonal. Cowboy boots also go well with knitted co-ords come fall and winter, ensuring this look will last well into the next part of the year. For a sleek ensemble, choose non-embellished, plain cowboy boots and mix with a ribbed knit set that will take you from brunch to the bar easily.

Styling tip: Remember that come fall and winter, cowboy boots will still look fantastic worn with tights. Go sheer if you want a more fashion look, or opaque tights for a more formal appearance.

how to wear cowboy boots with shorts shown on three women

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7. How to wear cowboy boots with shorts

When most people think of how to wear cowboy boots, Daisy Duke might spring to mind, however super short, cut-off denim is not the only way to wear shorts with cowboy boots. In fact, a longer Bermuda cut or mom short looks much more modern and directional with cowboy boots, especially if you add an oversized shirt or blazer to the mix. An ankle style boot also works best with denim, giving it a nice casual feel - perfect for festivals or sightseeing.

If you’re wondering how to wear knee high boots with shorts, choose a more formal cut of short - such as tailored or leather iteration - and team with a slim-fitting blouse, half-tucked knit or tweed jacket.

Styling tip: Grayson says that while nothing looks better than a casual t-shirt and denim shorts, adding a puff sleeved blouse creates a dressier look.

Do cowboy boots go over or under jeans?

For Grayson it’s a question of who is wearing them.

“For the fashion forward female, boots should go over your jeans, however, for work boots or men’s boots, they will remain under jeans,” she explains.

The act of tucking jeans into your boot is actually known as blousing and was common practice among early Texas Rangers, most likely out of necessity to avoid all the ticks out there in the wild west.

However, since the ‘80s, women have been tucking their jeans into cowboy boots -  Princess Diana was a particular fan of this look. To bring it into 2022, don’t just leave it for your jeans, slip your cowboy boots over your leggings, trousers and yes, even sweatpants. Basically, if it just looks like you literally threw your boots on in a hurry to leave the house, then you’ve got the modern day look nailed.

Jayne Cherrington-Cook

With over 22 years’ experience in journalism, Jayne has written about a variety of subjects. She spent the start of her career within the world of film, interviewing Hollywood stars, attending premieres and lusting after red carpet outfits, and then moved into fashion, launching websites for big magazines such as Look, Woman’s Own and Wedding and working with top fashion brands such as Westfield, LK Bennett and Hunter. 

Career highlights include dressing up as Kylie (in gold hot pants!) for a national newspaper and working on big fashion events alongside Giles Deacon, Henry Holland and Naomi Campbell.