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How To Wear Boots and Jeans

How To Wear Boots and Jeans

I love jeans and I love boots. Jeans plus boots makes me do an internal happy dance! 💃🏾 Nothing makes it feel more like fall than reaching into the back of the closet to finally pull out my boots. 

But with so many options, how do you choose the best combination of boots and jeans?

I’m glad you asked! That’s what we are going to be discussing today!


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I’ve divided the post into sections based on the type of jeans you want to style. Then I will tell you the best boots to wear with each type of jeans.

Lastly, I’ve included some styling hacks, because not every amazing outfit of the day starts out as perfection. Sometimes, you need to make adjustments to what you have so that you can make it work.

So, sit back, kick your boot loving feet up and let’s do this. 

Skinny Jeans with Boots and Booties

For now, we will stick to full-length skinny jeans, not the cropped versions. The fabulous thing about skinny jeans is that they can be worn with practically any type of boots, but there are some that work better.

Skinny jeans should be tucked into boots in this case or just left alone. Do not try to wear boots under your skinny jeans. In general, skinny jeans tend to have a good amount of elastic to give you that body-hugging, sexy fit.

 
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Even if you manage to get them over the shaft of the boot, it’s most likely going to end up feeling really tight and uncomfortable, bunching, or just not staying in place. This is not what you want.  I would not recommend sock booties with skinny jeans for the reason mentioned above.

You want a comfortable and stylish boot-jean experience. 

Knee-high and thigh-high boots work best with skinny jeans.  

 
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 Low cut booties are a good choice. 

Cowboy boots (or, cowgirl boots, if you prefer!) and skinny jeans make an awesome pair.

 
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Straight Leg Jeans and Boots

Good choices for straight leg jeans are sock booties, ankle boots, low booties, and potentially mid-calf. 

A sock bootie, as you probably imagine, would go under the jean leg, and would be an excellent choice for keeping out the chilly air. 

Have some freakin’ awesome leopard print booties or ankle boots? Check out this post for style tips and outfit inspiration on how to wear them!

 
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You could definitely also wear a low bootie with a straight cut jean. You won’t have to worry about the cut of the jean getting in the way of the boot itself.

A note about mid-calf boots and straight cut jeans: what the jeans are made of might help you decide whether you want these jeans tucked into your boots or whether you prefer to leave them out. If the jeans have elastic, you can probably tuck them in and have them stay in place (can you sit down in them comfortably?).  

If not, I would suggest you fold the jean into a cuff. The shape of the jean makes this a wonderful option because you don’t have to worry about things getting too tight around your ankles!  

What height should you cuff the jeans? Right to the top of the boot or about an inch higher looks the best!

 
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Bootcut Jeans with Boots

Bootcut jeans and boots were just destined to go together!  

 
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Stick to booties, ankle boots, and mid-calf on these, however for the optimum bootcut jean boots combinations. When these types of pants are tucked into boots, it might get a little awkward, because these types of jeans are cut pretty close to the body in the thigh area. Any boots you wear with this type of jean should be worn underneath the jean.

I especially love cowboy boots with the bootcut jean. It just has a natural, laid back vibe.

 
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Flare Leg Jeans and Boots

Your boot choice for flared jeans should be similar to the boots you would wear with bootcut jeans. Low booties, sock booties, and mid-calf boots work the best with this style of jean. 

But I would suggest either sock booties or mid-calf boots. Cowboy boots are not the best boots for these types of jeans. They just don't go well together.

Wide Leg Jeans with Boots

The beautiful thing is the wide leg gives you enough room so that you can really work the boots into your look without getting bunching or things getting too tight and uncomfortable.

I would recommend sock booties, ankle boots or even mid-calf boots to wear with this type of jeans. Although, you could, in theory, pull off a knee-high as well. Personally, I found this combination a little heavy and uncomfortable.

Cropped and Cuffed Jeans with Booties and Boots 

Cropped straight and skinny jeans

The perfect pair of boots to go with cropped jeans is the ankle boot. Most of the time, you won’t need to adjust the hem of the jean at all

Another good option is the mid-calf. Just add a cuff to the jeans and you’re good to go!

 
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Cropped bootcut and flare jeans

Your best option depends on how cropped your jean is, but in general, your goal should be to have the boot almost meet the hem of the jean. So if the jean is cropped just above your ankle, you can wear an ankle boot. If it’s cropped almost up to your knee, you want to wear knee-high boot

Cropped wide-leg jeans

For a chic look, sock boots look first-class with this type of jean. Any type of boot that hugs your bottom leg would work, even a boot with a little bit of a slouch. Opt for at least a mid-calf boot. 

For a more casual look, combat boots make an awesome choice as well. 

Bottom line: you want no more than about an inch of leg showing between the bottom of the jean and the top of the boot. But overlap is better.

 
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Jean Hacks You Might Find Useful

Do you like the color of your jeans but it’s the wrong cut? Or are you in a hurry and just don’t want to change? I’ve been there, and here are some useful hacks I’ve discovered that I pass on to you. 

Sometimes you need to make adjustments to your jeans to go with the boots.

Wearing your knee-high boots with the “wrong type” of jeans

You can actually make your straight or bootcut jeans into skinny jeans!

For this hack, you’ll need a good pair of knee-high or thigh high socks. I especially love this trick because, in the dead of winter, it also gives my legs a little extra warmth. 

You’ll need to fold the jean so that it will be comfortable to you, then pull the sock up over the jeans. Then you can easily pull your boots over your jeans and be on your way!

Wearing your cropped jeans into fall/winter

This works for that transitional time in the weather when you want to wear your boots, but you know that by lunchtime, you might be regretting that decision! Sometimes, the wash on the crop jeans goes better with the outfit. It’s a sneaky but cool way to get more wear out of the clothing you have

All you have to do is pair your cropped jeans with knee-high or thigh-high boots! This works best with skinny and straight leg cropped jeans.

Final thoughts about the best boots and jeans combinations

Boots and jeans are a hot combination for fall and winter. But with so many options out there, it can get pretty confusing to know which boot to wear with which jeans to get the cool girl pulled-together look you want. 

But wearing boots with jeans doesn’t have to be challenging! Hopefully, with these tips and tricks, you have the blueprint for some fabulous jeans and boots outfits!

For more fall fashion outfit inspiration, check out this post about fall fashion must-haves!

Cheers, Dears!


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