How To Wear Western Boots This Winter 2020

Western boots have some impressive style staying powder. Their origins go back centuries to Spanish cowboys and through both the American West and Hollywood. Today, they carry all of this history in a timeless look.

However, it’s still all too easy to drift from stylish to “is she wearing a costume?” when wearing western boots. You’ve got to know where the line is and how to skirt it just right. So before you go too cowgirl, let’s run through some simple outfits guaranteed to make your western boots look fantastic.

Western boots again in fashion

While in many parts of the world they’re always in fashion, 2020 saw western boots come back into the mainstream in a big way. Pushed forward by celebrities from Cardi B to Gigi Hadid, western boots have become centerpieces of everything from heavily western-inspired outfits to more standard streetwear.

Modernized classics

One important thing to know about the modern western boots trend is that these aren’t (always) what you imagine as a classic western boot. More often than not, what’s popular out there today are modernized updates to the classic. These might use new materials, patterns, or simply take the bolder elements of a western boot and make them a bit more subtle.

The entire western look

All that said, you don’t need to go for the “full western look” to pull off these boots. None of the 4 outfit ideas we explore below has a single rhinestone or cowboy hat. Instead, they show how modern western boots can work with everything from the most casual to more formal evening wear when styled right.

Great outfit ideas with western boots

Before you think “I could never pull off western boots” have a look at these outfits which probably use clothes you already have in your closet. Far from being shoes that just don’t go with anything, western boots can be a simple way to give all kinds of reliable outfits a stylish upgrade.

The midi dress

Even when they’re subtle, western boots are a statement piece, so it makes sense to wear something that shows them off a bit. A midi dress is perfect, falling at the mid-calf so you can show off the styling that so often defines the upper section of a western boot. But even if your boots are more plain there, you’ll still want to display the colors and materials.

The dress itself can be something chic and modern or absolutely classic. This is the chance to get the most out of something floral, polka dotted, or just anything that evokes classic mid and early-century American style.

The bike shorts

This is one of those outfits you probably hadn’t considered but it works surprisingly well. Ultra modern spandex bike shorts and super classic western boots are a strange match, but that style contrast is what can make this look so striking and effective. The key is to go for non-traditional western boots. That could mean black and white patent leather, or even a colorful vegan leather.

The name of the game is combining a classic western boot shape with non-classic materials to construct an outfit that’s all about interesting contrast. That said, this is definitely one of the more daring ideas on this list, so you might want to try out the others first.

The oversized coat

A simple but devilishly effective style is to pair an oversized coat with some cowboy boots. Underneath you can rock anything from jeans to a skirt, but the transition from a long flowing coat to mid-calf boots emphasizes both pieces and creates a simple but compelling outfit. Just be aware of materials here, a shinier leather boot will pair well with a coat that has some texture and vice-versa.

Best of all, this is one of those outfits that manages to be stylish and dangerously comfortable all at the same time, especially in cold weather.

The Friday evening dress

If you’ve got an old party dress you just can’t seem to get excited about anymore, here’s your chance to inject some life back into it. Even a fairly standard Friday evening dress can get a fun and folksy vibe when it’s paired with a more traditional leather western boot. Something a bit more formal can work well with more modern takes on the western boot. For example, a black dress with some black patent leather boots.

Whether you want to be on the subtle side or embrace the look, western boots are an excellent way to take a more serious outfit and lighten it up a bit.