How to Wear Cowboy Boots (A Woman’s Guide)

When I first suggested that my ex-girlfriend borrow a pair of cowboy boots to wear with her new outfit, her first reaction was “No way!” Then I realized that many other women probably have similar questions about how to wear cowboy boots. And so this detailed guide was born.

I’ll spare a second of silence to nod to the fact that cowboy boots can be intimidating. Standing tall, shaped like a heel, sporting a hefty price tag – just the sight of them is enough to strike fear in the hearts of many women! But they’re cuter than pies, will express your mood in one sweep, and will never, ever go out of style.

Women can wear cowboy boots with sundresses, maxi or gypsy skirts, or denim pants. Cut-off shorts can also be paired with cowboy boots to create an effortless look.

While they are most often associated with the fashion industry, cowboy boots were initially designed to provide comfort to cowboys while riding a horse.

How to Wear Cowboy Boots with Jeans?

Bringing boots and jeans together is not a fashion statement; it’s a personal affirmation that many women have pulled off, and so can you. Pair medium- to dark-washed jeans with different shades of boots, from white to black. Other colors like grey or brown can also work, but make sure the jeans’ color matches that of the boots.

There’s nothing like a combo of cowboy boots and dark-colored or medium-washed boot-cut jeans to add some character to your look. For a down-to-earth signal, match the good ol’ skinny jeans with cowboy boots.

You may be wondering how to pair your boots and jeans so that you achieve the look you want. Follow the tips below to showcase your inner cowgirl.

Cowboy Boots with Bootcut Jeans

These jeans are designed with a curvy or skinny person in mind. The style is tight from the hips down to the knees but flares out in the broader shape below.

The wider hems of these jeans make them ideal for slipping on over boots.

Cowboy Boots with Skinny Jeans

Skinny jeans are a casual staple, while cowboy boots can transform an outfit. Tuck your jeans underneath to show off your beautiful boots because, hey, you can.

Denim Shorts

Denim shorts and cowboy boots are an iconic pairing—and one that gives off a fun and fresh Western vibe. Pair your denim shorts with a crop top, and you’ve got a modern take on the classic cowgirl look.

Distressed Jeans

If you’re a country girl, try this: distressed jeans and cowboy boots. Only then will you understand what I mean when I say it’s fabulous.

Denim Skirts

You can step up to the plate with denim skirts and cowboy boots for a look that announces who’s in charge.

Are Women’s Cowboy Boots in Fashion?

Women’s cowboy boots are a must-have item for any fashionista, and designer brands are cashing in on the trend. Artists like Lady Gaga and Beyonce have been spotted wearing cowboy boots, as have countless fashion bloggers.

In 1923, the popularity of cowboy boots skyrocketed. Years after, artists from the motion picture industry (think: Marilyn Monroe, Dale Rogers, and Roy Rogers) were often spotted sporting cowboy boots.

In the late 1980s, Princess Diana of Wales wore a pair of brown cowboy boots with a formal blazer, jeans, and a white shirt. Her fashion sense rivaled that of other icons—like Jackie O.—and her love of boots made her a trendsetter.

Recently, country music star Taylor Swift and pop singer Britney Spears caused a stir by wearing cowboy boots with sundresses at public appearances. Those unusual pairings shook up the country aura that accompanied cowboy boots everywhere.

It doesn’t matter what you’re wearing—cowboy boots have the audacity to look good with everything. You can wear them with jeans, dresses, shorts, fringe skirts, jumpers, maxi skirts, and leggings. Cowboy boots are versatile enough to be worn with any style of clothing. Whether you’re a jeans-and-tees person or prefer to glam up, cowboy boots will seal your deal.

Can You Wear Cowboy Boots with Shorts?

Yes, you can absolutely pair cowboy boots with shorts. But the length of the shorts should be considered, especially if you want to appear modest and mature. If your goal is laid-back, pair your boots with above-the-knee-length shorts. For a playful and youthful style, rock your boots with short shorts.

You can pair your cowboy boots with mini shorts when it’s hot outside, as long as you’re comfortable wearing it.

The “Daisy Duke” look works best when your belt matches the color of your boots and when you throw a lacy cardigan over a tight t-shirt.

How to Wear Short Cowboy Boots?

With endless ways to wear a pair of western boots, it’s no wonder that this versatile footwear can be worn in all seasons. But how to wear cowboy boots? That’s up to you.

Ropers are easier to wear than cowboy boots since they are shorter. To wear them, make sure the shaft fits your feet well and hold the boot with your hands while guiding your feet into the toe portion of the boot. Slide your feet inside the boot until they fit comfortably, and there you go!

Short cowboy boots love being coupled with skinny jeans, bootcut jeans, sundresses, maxi skirts, or maxi dresses. If you want to look chic and bohemian, mix and match ropers with sundresses or maxi skirts. Going for a more authentic and casual feel? Pair it with your boot-cut or skinny jeans. If you would do anything for daisy dukes, let it be wearing them with ropers.

Can You Wear Cowboy Boots with Jeans?

You can rock a pair of cowboy boots with your skinny jeans. They look great tucked inside the boots, or you may choose to wear them over the top of your cowboy boots in a bootcut or western style.

The idea of matching boots with jeans comes from rodeo culture, where horse riders often wore cowboy boots over jeans on the ring. But they can also be paired with other fashionable items—dresses, maxis, and, sure enough, shorts.


With that being said, there are still many cowboys out there who are wearing their boots as they were originally intended: to ride a horse. From puttering around the barn to a day of working cattle, cowboy boots were designed for heavy-duty use.

But if the cowboy boots are the missing piece in your ready-to-kill ensemble, then, by all means, wear them.

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