Being from Houston, Texas I guess it’s no big surprise that I love a great pair of Western-style Cowboy Boots. In this post I’ll show you three timeless ways to wear cowboy boots and I’ll throw in some shopping links you won’t want to miss as well.

While the Western fashion trend is hot in 2021, there’s truly always a place in your wardrobe lineup for western cowboy boots. What makes them a terrific choice – besides being insanely comfortable – is their versatility. You can wear cowboy boots with dresses, skirts, jeans, leggings or shorts. It just takes a little thoughtful planning to pull them off in way that adds a stylish edge to your look.

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Before I jump into ways to wear cowboy boots, allow me to share one thing to avoid in real life (as opposed to on the runway, which usually involves looks few people can reasonably pull off).

Avoid putting together an outfit that’s too on the nose. In other words, don’t go into it trying too hard to look western. Putting all of your country western inspired pieces together into one outfit – or putting together an outfit that’s a stereotype such as cowboy boots with Daisy Duke denim shorts and a halter top – will result in looking like a costume.

Instead, pair your cowboy boots with pieces that are modern and stylish and wear them with confidence. If you would typically wear any other kind of boots with the outfit you’ve put together, substituting your cowboy boots will usually work and is guaranteed to boost your style to a higher level.

There are basically two styles of cowboy boots including western and roper. In a western-style cowboy boot, the heel is higher and angled. The shaft of the boot tends to be higher on western boot as well. Roper-style cowboy boots have a flat low heel, a lower shaft and, in general, a rounder toe. Both styles can be styled to look great with your outfit, but my personal preference is definitely a western-style boot which in my opinion looks more classy and feminine. You can read about the history of cowboy boots and see examples of the different kinds on this Wikipedia page that’s actually quite interesting if you’re into boots. While there is no “right” way to wear cowboy boots, there are some timeless combinations that work every time. I took some time to put together some outfit ideas for you below. Enjoy!

Stylish Floral Mini Dress & Western-Style Cowboy Boots

A short flowing dress looks amazing with cowboy boots, especially in a floral print like this Aurelia Mini Dress from Bohme. This feminine dress has a flattering v-neck, flutter sleeves and a stylish smocked bodice.

Pair the dress with these AMAZING Everyday Emma boots from Lane Boots and you simply can’t go wrong with this look. The Everyday Emma boot is both comfortable and stylish. The contemporary almond shape toe pairs nicely with the modern styling of a short mini dress.  Details like lacing and an unexpected silhouette. keep the look sleek and ultra cool.

Add the Robin Wristlet to this outfit for a little added polish. Lane Boots doesn’t just do amazing boots. They have a nice line of sophisticated western inspired bags as well. With supple leather construction, a zipper closure and a hip western pattern, this wristlet is exactly the right complement to this outfit. Overall, this look is easy, breezy and very cool.

So Pretty Smocked Midi Dress & Brown Suede Cowboy Boots

This gorgeous look is both western and a little bohemian at the same time. Love it! The flowing midi dress in ivory is fitted around the smocked bodice and features a flowing tiered skirt for a look that is romantic and sophisticated.

To the dress, add a pair of mocha suede boots and a stylish brown mini tote bag and you have yourself one feminine western look. Let the soft suede do the talking in Lane’s most loved tall boot, the Plain Jane. One of Lane Boots’ most popular styles, the Plain Jane boot is a tall style 15-inch western boot. Every pair is crafted from high quality suede, mated to a Goodyear welt, and Lane’s signature turquoise sole. A versatile style that blurs the line between contemporary fashion and western.

Finish this look with a sleek mini-tote bag from Bohme. With a single compartment, magnetic snap closure and adjustable strap, this small tote bag is both affordable and stylish. 

Leg Lengthening Bootcut Lucky Jeans with Western-style Booties

There is no more universally flattering style of jeans than this mid-rise jean in a classic bootcut. The style is slimming and your legs go on for days. I love this classic 5-pocket style with just a hint of stretch from Lucky. These jeans are made to wear with boots. You’re going to look great in this outfit!

What better way to give an updated look to a classic western style than with the perfect pair of booties? The Robin Bootie from Lane Boots offers unparalleled style with beautiful inlay features, a sexy 1.75” heel and a classic western shape and style. These will quickly become one of your favorites!

I love Olive Green with this outfit! This Grace Rolled Sleeve Top from Bohme is a soft olive neutral that adds a bit of color without overwhelming the outfit. The stretch knit material is soft and drapes beautifully.

Add a black moto jacket and this outfit that is damn-near perfect in my opinion! I love this jacket from Bohme that’s inspired by a leather moto jacket but made of polyester and spandex so it’s soft, comfortable and machine washable.

I hope you enjoyed this post about how to wear cowboy boots in 2021!

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