8+ Colorful Looks: What To Wear With Cowboy Boots

Trust me that I’m just as surprised I’m writing about what to wear with cowboy boots as you are. But when you move to the Southwest, it is expected, right?

And I’m learning that it’s quite fun to have an assortment of options in our closets

I wouldn’t say that cowboy boots are something you might think about wearing with your daily outfits. Even living here in the Southwest, I don’t see them as much as you’d think I would.

Maybe you have a pair hidden in the back of your closet from your younger days? Or maybe you just can’t imagine what to wear with cowboy boots so you never even bought a pair?

So I wanted to showcase how versatile cowboy boots can be, even in the springtime.

The secret of what to wear with cowboy boots?? It’s to stop thinking of them as cowboy boots per se, and think of them as just boots!! They are a fun option of footwear that can work no matter where you live.

I'm sharing 6 different looks here, and there are 2 more on my site.

1st Outfit: Jeans: Kancan ~~ Top: thrifted~~ Boots: Matisse-thrifted

2nd Outfit: Jeans: Style & Co~~ Cardigan: Belong Lifestyle USA~~ Top: thrifted~~ Boots: Matisse-thrifted

3rd Outfit: Jeans: Unablue Jeans c/o~~ Cardigan: thrifted~~ Boots: Matisse-thrifted

Jeans and What to Wear with Cowboy Boots

I feel like jeans are the most popular option of what to wear with cowboy boots. And with that prompt, I wanted to include 3 different versions of jeans.

First and foremost, the blue denim skinny jeans. This is one reason that those skinny jeans will always have a place in my closet. The fact that they are tight around the lower leg makes them incredibly easy to tuck into ANY type of taller boots.

Of course, I’m a huge fan of colorful jeans too, so I wanted to showcase a pair of red jeans with my tan cowboy boots. Again, the fact that these red jeans are a skinny silhouette makes them easier to tuck into the boots.

Insider tip: You can still tuck in straight-leg jeans. The best way is to pull them tight against the ankle and either tuck them into your socks or wrap a hair tie around them so they stay tight against your leg.

Then the third option with your jeans and cowboy boots is to wear either boot cut jeans or some type of wider leg jeans with the footwear. The only disadvantage of this option is you are hiding your cowboy boots. Then again, that could be an advantage depending on how you look at it.

BTW, this pair of wide-leg jeans was custom made for me. You can see 6 different options of styles that my friends and I all showcased here.

Pants: Ann Taylor~~ Sweater: hand-knit by me~~ Boots: Matisse-thrifted

Cropped Pants

Combining any version of cropped pants and your cowboy boots is another great way to make sure that your cowboy boots are on display.

Cropped or shorter-length pants CAN work for the colder weather if you combine them with footwear that covers the rest of the leg.

Insider tip: I’ve worn these same cropped pants with 5 different styles of footwear to show how versatile they are.

1st Outfit: Dress: Banana Republis~~ Top: Belong Lifestyle USA~~ Boots: Matisse-thrifted~~ Scarf: Gibby’s Frillery

2nd Outfit: Dress: thrifted~~ Tights: workout leggings~~ Boots: Matisse-thrifted

Cowboy Boots andDresses

Dresses are another perfect item of what to wear with cowboy boots. It’s not unlike the cropped pants in that most dresses will showcase the boots.

I’ve shown examples of wearing my tan cowboy boots with a midi-length shirtdress on the left and a tunic-length dress with leggings on the right.

But don’t think these are the only options. Wearing your boots with a maxi dress or a knee-length dress would also be just as stylish.

One of the reasons that these boots seem ideal with any cooler weather look is they cover your leg to provide warmth.

Yet, if you don’t need all of that coverage, there are many shorter options available. In fact, my friend, Cathie, wore a shorter pair called roper boots with a dress in this post.

1st Outfit: Skirt: my mom redesigned it~~ Cardigan: Chicos~~ Top: Steinmart ~~ Boots: Nordstrom-thrifted

2nd Outfit: Skirt: My mom made it~~Cardigan: thrifted~~ Boots: Matisse-thrifted

Skirts with Boots

In all reality, skirts are basically the same concept as dresses when thinking about what to wear with cowboy boots.

Therefore, in these examples, I created different styles with my cowboy boots and skirts.

In the outfit on the left, the overall vibe is somewhat classic with the tartan skirt and long cardigan. Whereas the outfit on the right has a more Western vibe since the skirt is made with pieces of leftover leather.

Make sure to check out my article where I share 2 more outfits worn with cowboy boots.

The author may collect a small share of sales from the links on this page.

Jodie Filogomo
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