How to Style Cowboy Boots: 8 Cute Outfit Ideas for Everyday Wear

how to style cowboy boots

I know I’m not the only one who thinks cowboy boots instantly add character to an outfit. Honestly, since I live in wine country, I see people wearing them often (and not just to country music concerts!)

Cowboy boots are super comfortable, cute, and easy to style with a variety of looks. I also love that there are so many types of cowboy boots you can choose from, all which offer their own personality. I have a mix of tall, short, and midi cowboy boots, and I reach for all of them for different occasions.

While I think cowboy boots can totally be worn on an everyday basis, I know that many people like to wear them to concerts, festivals, and even while wine tasting. Because spring and summer are just around the corner (and many of these events will start to take place), I thought I’d put together a simple guide on how to style cowboy boots.

All of these cowboy boot outfit ideas are easy to replicate and can be worn throughout different seasons. Another bonus? These pieces are all wardrobe staples that can be mixed and matched with other items in your closet—a win-win!

How to Style Cowboy Boots

1. A romper, a denim jacket, and a hat.

Rompers are one of my go-to pieces to wear during the warmer months. I mean, let’s be honest, is there anything more comfortable? They also happen to look really put together (and some are even quite dressy) despite how cozy they are.

Try pairing a white romper with tan or black cowboy boots, then add a denim jacket on top so you’re prepared for any change in the weather.

Also, don’t be afraid to rock a cowboy hat! If that seems like too much for you, you could always go with a regular wide brimmed hat.

strapless white romper
denim jacket
beige cowboy style hat

2. A white tank, mini skirt, and denim and fringe jacket.

Is it just me or does this skirt look like it was made to pair with cowboy boots? The chestnut color would look perfect with the bright contrast of a white tank top. Just tuck the tank into your skirt and throw on a denim jacket (I’m obsessed with this fringe one from Amazon) and you’ll be good to go.

Accessorize with a western-inspired belt or gold jewelry for an even more styled look.

white tank top
brown mini skirt
fringe denim jacket
heart buckle belt

3. A denim dress.

This is another no-brainer cowboy boot outfit which could not be easier to put together.

Denim and cowboy boots simply make a flawless combo, but sometimes it’s nice to switch things up and wear something other than a regular pair of jeans. That’s where this belted dress comes in!

You could honestly wear this outfit for any occasion, whether you’re going to a vineyard or meeting friends for happy hour. Also, I like the idea of pairing this dress with tall, heeled boots, but lower boots would also work (and would offer a more casual feel.)

denim belted dress
tall brown cowboy boots with heels

4. A graphic t-shirt and denim shorts.

Going for comfort? Try styling a graphic t-shirt with a pair of slightly distressed denim shorts. For the final touch, slip into your favorite cowboy boots and you’ll have a classic, ready-for-anything look.

p.s. If graphic shirts aren’t really your thing, opt for a plain white tee instead!

graphic t-shirt with a bronco on it
oversized graphic coors t-shirt
distressed denim shorts
tan cowboy boots

5. A tank top and colored shorts.

Sometimes the best outfit is a simple one. Ideal for hot days (or events/concerts), the combo of a tank and a pair of shorts feels feminine and fun.

Like I mentioned above, sometimes it’s nice to wear something other than denim, which is exactly why these shorts would be perfect to style with cowboy boots. They’re such a pretty color and would work throughout spring, summer, and even into the fall. They also come in white and dark gray!

black western tank top
tan tank top
tan denim shorts

6. A button-up shirt and shorts.

If I had to guess, I would say it’s safe to bet that you have a button-up shirt in your closet. I personally think a button-up is an essential in every wardrobe, and it just so happens to make a great top choice when styling western boots.

Need a button-up? This one is a great deal (under $40!) from Amazon. This white pick is a little more pricey but it would go with everything.

For your bottoms, you could go with a denim skirt, pants, or shorts—whatever you’re feeling in the mood for!

brown corduroy button down shirt
white button down shirt
blue denim shorts

7. A maxi skirt and a tank top.

If you follow me on Instagram or if you’ve been reading the blog for a while now, you likely have noticed that I wear a lot of maxi skirts. I think they’re insanely comfortable yet they look so elevated.

I’d style this black skirt with a basic white tank and a pair of black cowboy boots. You could also add a denim jacket or a cardigan for extra warmth. This would look really cute for a wine tasting event!

white tank top
black maxi skirt
tall black cowboy boots
black cowboy boots

8. A matching skirt set.

Last but not least, who doesn’t adore a good matching set? These skirt sets are so cute for the spring and summer and would pair perfectly with cowboy boots.

For the times that you don’t want to wear boots, these sets would also look adorable with white sneakers or heels.

mauve matching skirt set
black matching skirt set
white felt cowboy hat

Cowboy Boot Outfit Ideas

cowboy boot outfit - mini skirt with a white tank top and cowboy boots
cowboy boot outfit - denim shorts with a strapless top and cowboy hat and boots
cowboy boot outfit - white denim skirt with a white tank top and denim jacket with cowboy hat and boots
Erika's Signature

Hi! I’m Erika and I live in Sonoma County with my high school sweetheart and two kids. Follow along to find home inspiration, delicious recipes, and the inside scoop on all things wine country.

Get Social

Leave a Comment