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

So, you’ve got a pair of cowboy boots, or you are planning to buy some cowboy boots and you’re wondering how to wear them?  You’ve come to the right place.  For women, you have lots of options when it comes to wearing cowboy boots and you can use your cowboy boots to show off your own unique style!  Let’s chat about your options...

Women can wear cowboy boots with a matching dress, skirt, pants, and or shorts.  Cowboy boots can be paired with denim or a sundress. You can also pair your cowboy boots with a maxi or gypsy skirt.  The best pants to be paired with cowboy boots would be denim. Ladies can easily pair cut-off shorts with cowboy boots. 

Cowboy boots are linked to the fashion industry rather than its primary purpose. These boots are typically used to give comfort to cowboys when riding a horse. Cowboy boots have become an iconic fashion staple from the beginning of the 20th century up until now. 

How to Wear Women's Cowboy Boots with Jeans?

A lot of women like to pair boots and jeans, and it looks classic and chic. You can use different shades of jeans from medium to dark-washed. You can also use other colors like white, black, grey, or brown, but the color of the jeans must match with the color of the boots.

Women can wear cowboy boots with various types of jeans. A classic or traditional style would pair cowboy boots with a boot cut jean. A casual-modern look would pair your boots with skinny jeans.  When wearing cowboy boots with jeans, it's recommended to wear dark-colored to medium-washed jeans.

But how are you likely to pair those correctly? There are various types of cowboy boots and multiple kinds of jeans. In order to have a good outfit result, matching your boots with jeans is essential. Follow the tips below to showcase the cowgirl look in you.

Cowboy Boots with Bootcut Jeans

Levi's Women's 725 High Rise Bootcut Jeans, Lapis Dark Horse, 29 (US 8) L

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If you are curvy or skinny, this style of jeans is typically good for you. The design of these jeans is tight in the hips down to the knees while giving it a widened style below.

The widened-down design of these jeans allows you to slip your boots in.

Cowboy Boots with Skinny Jeans

Levi's Women's 311 Shaping Skinny Jeans (Standard and Plus), Maui Views (Waterless), 31 Regular

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Skinny jeans are very casual, and cowboy boots can hype up your outfit. You can tuck your jeans inside to showcase your beautiful boots.

Denim Shorts

luvamia Women's High Waisted Shorts Frayed Raw Hem Ripped Denim Jean Shorts Blue Color, Size M

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Denim shorts paired with cowboy boots provide a casual and comfortable look. This outfit channels the modern type of cowgirl look. You may use a crop top to match.

Distressed Jeans

Resfeber Women's Ripped Boyfriend Jeans Cute Distressed Jeans Stretch Skinny Jeans with Hole

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You can never go wrong in matching distressed jeans and cowboy boots. This look showcases a modern type of cowgirl look. If you are a country girl by heart, this one is for you.

Denim Skirts

GRACE KARIN Women's Casual Button Down Denim Skirt High Waist Bodycon Pockets Jean Short Skirt Dark Blue XL

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You can rock the chic cowgirl look by matching your cowboy boots with a denim skirt.

ZESICA Women's Bohemian Floral Printed Wrap V Neck Short Sleeve Split Beach Party Maxi Dress Royal Blue

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This outfit is easy to pull off will give you a stylish casual look.

Are Women's Cowboy Boots in Fashion?

Women’s cowboy boots are definitely in fashion! A lot of designer brands showcase cowboy boots in their runways. Most artists wear cowboy boots to showcase their own fashion sense and personalities.  Cowboy boots are always on top of the fashion lists and are considered to be a fashion staple. 

In 1923 this became a fashion trend. Years after that, artists from the film industry were also famous for using cowboy boots. This trend was also popularized by Hollywood stars like Marilyn Monroe, Dale Rogers, and Roy Rogers.

In the late '80s Diana, Princess of Wales, wore an unusual combination of brown cowboy boots paired with a formal blazer and jeans. She would pair different outfits with cowboy boots, and her knack for boots made her a fashion icon. 

Ariat Women's Heritage R Toe Western Cowboy Boot, Distressed Brown, 8 Wide

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Recently, famous artists like Taylor Swift and Brtiney Spears broke the usual trend by pairing cowboy boots with sundresses. The cowboy boots fashion creates a heavy association with country song music. 

Cowboy boots are so versatile that they can be paired with any clothing style. May it be jeans, dress, shorts, fringed skirts, jumper dress, maxi skirts, and leggings. Whether you have a chic, classy, authentic, or street style, these boots are perfect for hyping your fashion sense.

Can You Wear Cowboy Boots with Shorts?

Absolutely yes. In pairing cowboy boots with shorts, the length must be considered. Pair your cowboy boots with above-the-knee-length shorts to have a simple and modest look. To have that playful and youthful style, pair your boots with short shorts. Boot height must be considered if you want to pair it with shorts.

When you think of wearing cowboy boots in summer, you can pair them with a daisy duke. However, the use of it depends on your level of comfort. This outfit is effortless to pull off and is suited for hot summer days.

When pairing your boots with a Daisy Duke, add a belt that matches the color of your boots. You may also use a laced cardigan to cater to that boho-chic style.

How to Wear Short Cowboy Boots?

Roper Women's Flotus Western Boot, Brown, 7

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It seems like there is endless inspiration for how to wear short cowboy boots or roper boots. This versatile footwear is for all seasons since you can match it with different clothing styles. Wearing them depends on your fashion style.

In comparison to cowboy boots, the roper is easier to wear since it is shorter. In wearing them, you just have to make sure that it fits your size well. Then, hold the shaft with your hands to guide your feet in entering. Point your feet sliding down inside into the toe portion of the boots for a perfect fit, and there you go.

You can pair your short cowboy boots with denim shorts, skinny jeans, boot-cut jeans, sundresses, maxis, and skirts. To have a chic boho vibe, pair them with sundresses or maxis. For an authentic and casual look, pair it with your bootcut or skinny jeans. To have a young and playful look pair them with daisy dukes.

Can You Wear Cowboy Boots with Jeans?

You can wear cowboy boots with jeans. This is the original classic style of wearing cowboy boots. You may tuck your skinny jeans inside your boots to showcase your footwear. You may also wear a bootcut or western jeans over your boots. Your choice depends on your style preferences and comfort.

The idea of pairing them with jeans comes with how rodeos wear them. They wear classic jeans and boots as the best pair while riding horses. Other fashion trends, including matching your boots with a dress or maxis, or skirt, or shorts..


Cowboys historically wear cowboy boots. However, over time it changes into a classic style that even the present generation is wearing. 

Different types have popped up, showcasing different styles and personalities. Over time, cowboy boots are worn in many different situations, in addition to being great work boots.

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