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How to Wear Western Ankle Boots

A western ankle boot is probably not the first style you would think makes our Top 6 Boots for Fall, but something about them is sweet and super wearable.

And if you are like me and lean toward classic style with a twist, this is a great twist for the season. 

Certainly, you can wear these boots like any other ankle boot. They sit under a pair of straight or bootcut jeans perfectly. Then, throw on a sweater, and you’re dressed. 

But you know I like to make pieces purposeful, so let’s create two very different looks using this that you can wear yourself or use as inspiration. 

How to Wear Western Ankle Boots

Brown western boots with black jeans, neutral fair isle sweater, black crossbody bag, and gold hoops or with an olive utility dress, olive turtleneck, olive and gold drop earrings, olive clutch

Dolce Vita Silma Western Booties in dark brown

Western Booties, $130 

Our featured boots are from Dolce Vita. They are the nicest version of the style I have found, made well and in available in a range of neutral colors, but I would go with dark brown or “truffle” suede. 

Either will work with a a variety of looks. 

Half sizes are available in starting at a 5 – 13. 

With Jeans and a Sweater 

Brown western boots with black jeans, neutral fair isle sweater, black crossbody bag, and gold hoops

Straight Jeans, $60 | Fair Isle Sweater, $25 |  Vegan Saddle Bag, $40 | Hoop Earrings, $14 

A western boot and a fair isle print work so well together. 

The sweater above is from Old Navy, and it’s only $25

We’re showing it in their neutral combo, but the JUST added a warm option and it’s so pretty. Either would be a lovely Thanksgiving week sweater. 

Available in regular, tall and petite, in XXS – 4X. 

For jeans, everyone on TiKTok (I watch so you don’t have to) is raving about the Levi’s 724 Hight Rise Straight Jeans. So I ordered them, and like them very much. I did have to go up a size. 

I’m showing them in black but there are lots of washes to choose from and a range of lengths and sizes, including plus. 

And you can’t beat $60 for a pair of jeans.

Depending on what kind of jean you wear, you can do a few things with the boots. Skinny jeans will sit in the boot or just skim the top, a straight or bootcut will sit over them.

For a casual bag, I’m reusing the Quince Vegan Leather Crossbody, at only $40, lots of positive reviews are coming in on this. And because I can’t help myself, our favorite hoops from Amazon. There are a few sizes to choose from, I wear the smallest size, 20mm almost every day. 

With a Dress

Brown western boots with an olive utility shirt dress, olive clutch, olive turtleneck, and gold and olive drop earrings

Utility Shirt Dress, $72 | Turtleneck Top, $23 Earrings, $8 | Clutch Purse, $30

Next, consider a dress.

It could be a loose-fitting sweater dress – another fantastic option for Thanksgiving, or pair it with a flowy, floral high/low hem maxi dress.

This shirt dress from Banana Republic Factory is a fresh, cool look.

It’s available in a few colors, including a beautiful navy and brown, in regular, tall and petite in XXS -XXL

Side note: this dress would also look gorgeous with knee high boots. The dress will cover a part of the boot and you get a very chic, Ralph Lauren inspired outfit. 

You can wear it as is, or, if you’d like, add a turtleneck underneath. You’ll want something fitted in a thin knit, like this inexpensive option from Old Navy. The color doesn’t have to be a perfect match, just in the same family.

I added a fold over clutch, this one from Amazon is an awesome find. And then, this funky, $8 pair of earrings rounds out the outfit. 

And I know you’re going to ask about your legs. So, let’s talk about it. 

I would go bare legged and wear no-show socks in my boots.

I wear these no-show socks I found on Amazon. 

You could wear tights, but that gets complicated and messy with the color. The only way I think that would work well is if you wore a black dress, black tights, black boots.

So if you’re concerned about being too cold, stick with pants and don’t try to make this outfit work. 

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How to Wear Western Ankle Boots

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Wednesday 26th of October 2022

Love this post. I’m obsessed with that dress. There’s so many different ways you can wear that is so classic with a modern twist. you mentioned high boots, what’s the trend right now with them I feel like I have a whole closet full and I’m not sure if they’re dated. Or even a modern take on how to wear them. It seems as if no one wears them over jeans and leggings anymore.


Wednesday 26th of October 2022

Wondering the same about my tall black riding boots. How can I wear them in style this season and into the winter that’s still casual and not a sweater dress?