What To Wear With Cowboy Boots And Jeans

If you haven’t grown up in a culture where wearing cowboy boots is normal it can feel a little intimidating. 

It’s a whole culture on its own with a lot of different subcultures. And how you dress is going to put you into one of those many buckets. And like it or not that is going to be how people make a judgement on you. 

If you are going to something like a county fair and you don’t want to appear like a “dude” ie someone who is trying to fit in but has no idea what they are doing and gets eye rolls from the locals you are in the right place.

Let me explain the different styles or buckets of country lifestyle subcultures to help you make a choice about how you should dress and present yourself. Cool?

Different Country Lifestyle SubCulters Of Dress

There are all kinds of different kinds of country lifestyle ways to dress and just because you have on a pair of boots doesn’t make you country. You have to earn your country life status. It doesn’t mean you live on a farm or even raise livestock. 

You have a calm and in-control demeanor about you and you live life with honesty. You earn trust and don’t force your way in. If you try to present a certain way but someone stiffs out the lie. You will have a very hard time earning that trust back.

Now that we’ve gotten that covered let’s get into the different styles of country dress.

Farm Country vs Hills and Woods Country Vs Western

Unless you live the life you may not even catch this. But there are two different styles of country. 

There is farm country. There are the raised livestock, shown in 4H or FFA, and might seem a little less “grungy” than the hill country culture. 

I didn’t catch this until I married a “woods country” man. I grew up on the farm countryside of the tracks. 

I am probably going to step on some toes here but this is how it is. 

Indicators Of Farm Country 

• Camo is for hunting. 
• You have dress boots and chore boots. 
• Brighter colors. But still sleak
• A bit more flashy designs.
• Girls love their jewelry, makeup, and hair products. 

Indicators Of Hills Or Woods Country

• Camo is worn even when you aren’t hunting.
• They are not as well groomed. – For guys shaving or trimming hair is less of a priority. And girls don’t tend to have as much of a hairstyle.
• Makeup really isn’t a thing.
• Neutral colors are number one over bright and flashy.
• They rarely wear jewelry if at all.

Indicators Of Western Style

• Even brighter colors than “farm-style” people.
• Lots of fringes. 
• Geometric shapes on fabrics. 

Now there is more that I could get into but these are the indicators associated with dress. If you are on the east coast don’t go trying to fit in by wearing western clothing to the nines. This is how you will get the biggest eye rolls this side of the Mississippi unless you came from the West. 

Everyday Wear – “get the job done”

If you are helping with chores at a farm you need to be ready for the job and not be concerned if your clothing gets damaged. You want to earn your stripes with someone? Wear the right clothes to a job and be ready to work. 

You want to wear this type of cowboy boots for working on a job. Basic style with a good amount of tread and NO HEEL like you might invitation for the classic boots you see in a storybook or tv.

You want to wear strong fabric casual jeans for doing work.

Now I will say you will see girls at the fairs wearing shorts with their boots. If it’s hot an you are not likely to get stuff in your boots then this is acceptable. But guys… yeah it’s teetering on the edge of weird. 

Classic Style – Clean and Presentable

A lot of people think of Western style with lots of fringe as the classic look for wearing “country style” clothes but that is not the norm. The classic style is a nice pair of dark wash jeans that fit nicely and for girls flared jeans show a bit more style. A nice pair of stylish jeans have thread stitching that shows, and a nice pattern on the back pocket, and fight snugly around the upper leg.

You can still wear a nice pair of clean and not severely used pair of cowgirl boots if you are wanting to be comfortable. 

Girls have a lot more leeway with what they can wear for their tops but try and keep it respectable. Anything from a nice clean-style t-shirt with jewelry to a dressy silk top can go with this look.

This is pretty much what you would wear to anything in town that isn’t a wedding or Sunday church.

Show Style – If you are showing livestock

I am bringing this up because this style will get the eye roll if you wear it to someplace that it doesn’t fit. 

Boots: Here we are talking your best western boots that are clean, likely have a heal, and look nicer. 

Jeans: Here we want as fancy as possible and almost slide into the western wear. You want an extremely dark wash and if you can afford jeans with embellishments go for it. (this often means you are talking $80-$200 for one pair of jeans) 

Tops: Flashy button-ups with bright colors and snaps. 

** True show people don’t wear fringe on their clothes because they will get in the way and possibly spook the animal. This is one indicator of someone trying to fit in but has no idea what they are doing. 

Dressed Up – Fancy Once In A Blue Moon

This is the style where women can wear dresses that may not seem like they fit the regular wear and style of country outfitters. Often lacy, a black or white dress, and extremely classy. 

For the guys you get to keep the denim jeans but a nice solid button-up shirt and a nice pair of dress boots.

​Finding The Right Jeans

My top jean cut recommendations are boot cut and slim fit if you are looking for dressy jeans. The key is having them brighter around your upper legs and lose at the bottom.

The next time you find a really good-fitting pair of jeans it’s a good idea to buy different colors or multiple pairs of them to store away for later. Finding jeans again after the fact is almost impossible.

Different Brands Of Jeans And Their Style Trens

​Wrangler jeans tend to be more casual wear and are good to wear on a daily basis. 

Levi’s jeans can have some dressy options but still not quite the Western vibe. 

Ariat Jeans are a true country girl’s brand of jeans. They have a great cut style and great stitching patters that contrast with the jeans.

Here are some of the best women’s jeans I have found and love. 

Start With How You Are Wearing Your Paints And Boots Before You Decide On A Top

When it comes to putting together an outfit with cowboy boots and jeans, it’s important to start with how you are wearing your pants and boots before you decide on a top. The way you style your jeans and boots will greatly influence the overall look and feel of your outfit.

Always wear your jeans over cowboy boots instead of tucking them in unless you are a girl wearing shorter cowboy boots and skinny jeans or straight-legged.

This is a more casual and effortless look that works well with different jean cuts, such as straight-leg, boot-cut, and wide-leg jeans. By allowing the boot to peek out from under the pant leg, you create a balanced and visually interesting silhouette.

Like I said there is an exception to this rule – skinny jeans. Skinny jeans are designed to hug the contours of your legs and tucking them into your cowboy boots can create a sleek and streamlined look. This style is great for showcasing the shape and structure of both the jeans and the boots.

Now that you know the importance of how you wear your pants and boots, you can confidently choose a top to complete your outfit. Whether you opt for a flowy blouse, a fitted t-shirt, or a trendy jacket, your choice should complement the style and vibe of your jeans and boots.

What To Wear With Slim-Fit Jeans or Skinny Jeans Tucked Into Boots

When it comes to styling your skinny jeans with cowboy boots, there are a few outfit options. One popular choice is to tuck your skinny jeans into your boots for a sleek and streamlined look especially if you are wanting to show off the top of the boot. 

Some of my favorite cowboy boots for girls to do this with are boots that have a longer more narrow shaft of the boot. This is a great option if you want to be nice and dressed up.

For a more casual vibe, you can also roll up the pant legs of your skinny jeans to create a cuff just above the top of the boots. This adds a playful touch and allows the boots to take center stage. It’s a great option for those days when you’re feeling a bit more laid-back.

What Tops To Wear For Different Looks

Now that you have the jean and boot situation figured out, it’s time to choose the perfect top to complete your outfit.

A fitted t-shirt with an oversides sweater is one of my favorite classic pairings. Adding flannel shirts can also work well with this style. 

If you want to dress up this type of style you can add some jewelry and make sure your hair and makeup are well done.

What To Wear With Ankle Boots And Cropped Jeans

Looking to rock a trendy and modern look with your ankle boots and cropped jeans? Well, you’ve come to the right place! Styling ankle boots with cropped jeans can create a chic and cool outfit.

First off, there are so many different combinations you can try. For a more casual and relaxed vibe, pair your chunky ankle boots with cropped boyfriend or mom jeans. The slouchy fit of these jeans perfectly complements the chunkiness of the boots, giving you an edgy and laid-back look. However, don’t wear super loose jeans if you are still trying to get a country lifestyle vibe. 

If you want to dress it up a bit, opt for a sleek pair of pointed toe ankle boots with your cropped skinny jeans. The sleekness of the boots adds a touch of elegance to the overall outfit, making it perfect for a night out or a fancy lunch date.

What Tops To Wear With This Cut

This is very similar to what you would wear with skinny jeans. You can dress them up with a fitted button-up shirt or a nice t-shirt fabric top with jewelry and a sweater.

Play around with different fits, colors, and washes to find the perfect combination that suits your personal style. 

What To Wear With Stright Leg Jeans, Relaxed Fit, Or Boot-Cut Jeans Over Top Of Your Cowboy Boots

For a casual and relaxed look, pair your boot-cut jeans with a t-shirt of any style. 

For a more dressed-up look put on a classic collared shirt or a more elegant cut shirt. Whether it’s a solid color dress shirt or a cool plaid or flannel shirt, this combo gives you effortless style.  – Roll up the sleeves for a more laid-back vibe.

Add Layers For A More Dynamic Look

If you’re going for a more rugged and timeless look, you can throw on a denim jacket over your boot-cut jeans. Now I’m not a fain of the double denim look but it does work for some people. This classic piece is a perfect match for your cowboy boots, creating a rugged Western vibe.

Just make sure to mix up the colors of your jacket and jeans to avoid the dreaded “Canadian tuxedo” look. Opt for a darker-wash denim jacket with lighter-colored pants or vice versa.

Adding a dressy jacket or cardigan will add some warm and inviting vibes to the outfit by adding texture.

Take your boot-cut jeans and cowboy boots combo to the next level with a sport coat. This sharp addition instantly adds a touch of polish and refinement to your outfit. Choose a sport coat in a complementary color to your jeans and pair it with a crisp shirt for a look that’s perfect for a night out or a special occasion.

What To Wear With Straight Cut Jeans Over Cowboy Boots

When it comes to pairing straight-cut jeans with cowboy boots they are more of a get the job done pair of jeans. Unless it is for guys they are not meant to be dressy. 

So if you are looking to be comfortable find your favorite pair of blue wash straight-leg jeans and wear them with your daily wear cowboy boots.

Opt for simple tops like a basic t-shirt or a classic button-down with this combo.

How To Choose A Top To Go With Your Jeans And Boots

Finding the perfect top to pair with your jeans and cowboy boots is all about striking the right balance between practicality and style.

The type of top you choose will depend on the occasion, your personal style, and the fit of your jeans. Here are some tips on how to choose the right top to complete your outfit.

To show off your boots: If you’re rocking a bold pair of cowboy boots and want to let them shine, consider opting for a more understated top. A simple white or black t-shirt is a classic choice that allows your boots to take center stage. Alternatively, you can go for a neutral-toned blouse or sweater to create a chic and refined look.

Bold statement all around: On the other hand, if you want to make a statement with your outfit, go for a bolder and more eye-catching top. A brightly colored or patterned blouse can add a fun and playful touch to your ensemble. Alternatively, you can choose a top with interesting details like lace, embroidery, or ruffles for a more feminine and romantic look.

Keep in mind that not all cuts are for every body type and if you are not comfortable in a certain cut of jeans then don’t try to force yourself into a cut that isn’t the best jeans for you.

Remember, the key is to have fun and express your personal style and be confident in what you are wearing. People can tell when you are just showing off or not at all comfortable in what you are wearing.

If you don’t know what your style is yet, experiment with different tops, blue jeans, and styles to fined the perfect fit and discover the perfect combination that makes you feel confident and fabulous in your jeans and boots. Hold them up to yourself in the mirror and try to ask yourself how you feel in that style. 

And if something doesn’t feel comfortable to you… Be willing to admit it. That is totally fine if the country lifestyle fashion isn’t for you.