Which Pants to Wear with Cowboy Boots?

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The cowboy boot craze is going strong and we are here for it! Cowboy boots are so versatile and there’s not much that won’t work with them. You can wear them with pants, skirts, dresses, even shorts. Of all these options, pants are easily one of the most timeless looks with cowboy boots. So which pants are best? We’ve rounded up some of the hottest looks with cowboy boots for you.

When it comes to pants, jeans are king – overall, boot-cut jeans and skinny jeans are two of the best options you’ve got to pair with cowboy boots. But the right casual suits and dress pants can actually work as well. Here are our conditions:

Any pants worn with cowboy boots need to be either cut wide enough so they fall over the boots without the boot shaft creating a visible bulge, or cut slim enough to tuck into the boots without bunching at the ankles.

As long as you have a smooth line all the way down to the boots, they’ll shine!

Which pants to wear with cowboy boots?

But as we mentioned before, pants are far from the only option to pair with your cowboy boots. Really, they’re probably more versatile than you think. We address some common questions below – read on to take a look at some more dos and don’ts for this iconic style.

What Should You Not Wear With Cowboy Boots?

It’s difficult to go wildly wrong with bottoms for cowboy boots – they lend themselves well to most pants as well as skirts, dresses, and shorts for women. But you can definitely take a wrong turn when crafting an outfit around cowboy boots. We’ve talked about classic pairings, now here are a few things we recommend avoiding as you craft your outfit.

Avoid pairing them with other distinctly Western pieces, unless you’re going for a full-on cowboy look. Cowboy hats and fringed pieces add to the Western aesthetic, and frankly it may look like Halloween came early for you if you’re rocking these all together.

Avoid wearing spurs on your boots unless you’re actually hopping on a horse in the immediate future. Spurs are for riding, not every day style.

Avoid accessory overload. This is mostly for the ladies – no matter how casual or fancy your outfit is, cowboy boots already provide a killer focal point and act as an accessory on their own. Let them stand strong, there’s not usually much need to go overboard with a bunch of other accessories. A classy watch, some simple jewelry, and/or a pocketbook will do the trick just fine.

Avoid wearing them with suits that fall into a category fancier than business casual – cowboy boots can do a lot, but at their core they are a casual style. They can work with more formal outfits, but usually have the effect of toning them down, which likely isn’t what you want with a suit.

Where Should and Shouldn’t You Wear Cowboy Boots?

With their casual nature, cowboy boots are better suited to more lighthearted functions. We recommend wearing them at bars, casual restaurants, fairs of any kind, and rock or country concerts. Cowboy boots are also great for most styles of step dancing, and of course for horseback riding.

On the contrary, cowboy boots don’t typically fit in at more upscale or serious functions. Fancier restaurants and presentations like political functions may not be the best choice for your boots.

Is it OK to Wear Skinny Jeans With Cowboy Boots?

Absolutely! Skinny jeans are a perfect match for cowboy boots, particularly for women. Cowboy boots have a distinct style all their own, and these days you can find them with more and more detailed designs. Pairs may sport intricate stitching or printed designs, and no color is off the table. Skinny jeans tuck right into cowboy boots with virtually no bunching at the ankles, creating a smooth look that allows the design of the boots to take the spotlight.

Styles like skinny jeans and other options that don’t cover up the boots will always be aided by the fact that cowboy boots themselves are extremely clean cut. Cowboy boots are quite a distinct style, and part of that comes from their clean, straight lines, from the shaft to the shape of the toe. No cut is incidental.

Should You Yuck Pants Into Boots?

That will depend entirely on the style of the pants. Remember the conditions we discussed earlier? We just looked at skinny jeans, which of course will tuck naturally into boots. You’d be hard-pressed not to. And of course cowboy boots are lend themselves well to the aptly named boot-cut jeans, designed to fall neatly over boots and hover just about the ground. This look is classic and we don’t see it ever going out of style. Pants with a wider leg don’t need to be tucked in – this will bunch up the pants at the ankle and create a messy, unkempt look.

How Should a Woman Wear Cowboy Boots?

Women have SO many options for styling with cowboy boots. Arguably, women have far more choices than men. While the boot-cut pants pairing is a match made in heaven for everyone, women can also can rock the skinny jeans, or shorten up the hemline and style cowboy boots with a dress or skirt.  Let’s look at some of these styles.

Skinny Jeans

Like we mentioned before, skinny jeans tuck smoothly into cowboy boots and let the design of the boots shine. In this lovely example, the model is warning dark blue skinny jeans paired with a collared white shirt, a floppy hat, and her cowboy boots. These neutral colors are clean and classy, and let the inlaid design of her boots stand out.

Shorts

Aside from pants, women can also put together cute, stylish outfits with shorts, particularly denim pairs. Shorts are awesome for letting boots stand out, given the contrast of the boots against bare legs rather than pants. Take a look at the outfit below. Her simple denim shorts and plain long sleeve henley shirt really let her ornate, multicolored boots take the spotlight.

Dresses

This is a perfect example of using cowboy boots to tone down a fancier outfit. She’s taken a smooth bodycon dress and matched it with a blazer and dark cowboy boots. The deep black and olive tones shown here complement each other and both the blazer and boots add a casual flair to what could otherwise easily be quite a formal outfit. The blazer adds coverage, and the boots give off a far more casual vibe compared to high heels.

Skirts

This example covers two fabulous styles to rock with cowboy boots – skirts and animal print! Animal print provides lovely contrast to cowboy boots, complementing without matching in aesthetic. This particular skirt is slit in the front, letting it split and drape around her legs as she sits, bringing the boots more prominently forward as a focal point. None of the colors are matching, but they’re all neutral and they flow together.

So many options! Remember the basic conditions for pants with cowboy boots, and you’ll never go wrong. There’s a reason that we have a style of pants literally named for the purpose of wearing with boots. It’s pretty foolproof. But at the end of the day, despite every list of dos and don’ts you may come across, you can make almost anything work with cowboy boots. We’ve shown you some classic and some alternative styles, now you can go out and make these looks your own.

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