how to wear ankle boots with jeans

Your Guide on How To Wear Ankle Boots (and More) With Jeans, Plus Tips for Always Getting It Right

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We all know that a classic pair of boots and a solid pair of jeans are wardrobe essentials. And we even all know that they look great when worn together. But what’s a little less known is how to wear them together. How tall should the boots be? How short should the jeans be? What’s the right style for both? Is there some sort of magic formula that ensures the right look every time? If these questions have been swirling around in your head and you’ve been wondering how to wear ankle boots with jeans, I broke down the different looks to a math formula (I got out the tape measure and all) and put together this ultimate style guide!

Before we get into all the different ways to wear ankle boots and jeans, it should be mentioned that a lot of this is personal preference and based on the way that you like to wear your jeans.

I know this can be confusing to those who want to know whether or not they’re wearing something the “right” way, but when it comes to fashion, there really are no hard rules. However, there are guidelines, but ultimately, you should wear what you like and feel comfortable in.

This post can give you the tips and tricks and visual examples needed to pick the right choice for you-because sometimes you’ve just got to see it to know if you like it or not!

But with that being said, jeans and boots belong to my signature outfit combination, so I’ve experimented a lot. (When I die, bury me in a blazer and basic t-shirt too, please.) And though I’m not a trend-focused person, part of my job is knowing “what’s out there”, and after 6+ years of studying various looks, this is what I think works.

Okay! Let’s start with the jeans styles. I picked four major styles that almost everyone has in their wardrobe (or should):

the jeans to wear with ankle boots
  • Straight Leg Jeans

Spoiler alert: These are, in my opinion, one of the best types of jeans. There are slight differences between slim and straight-leg jeans, but for the most part, they are pretty similar so most of these rules can work for both.

Have a pair of mom jeans instead? Mom jeans are classified by the waist, hips, and the way they fit. Most mom jeans have a slim ankle cut, so it’s possible you can use these styles interchangeably too.

In this post, I’m wearing straight jeans from Madewell’s The Perfect Vintage Straight Jean Line. Definitely recommend!

  • Skinny Jeans

Not the most current style of jeans anymore (straight is the new skinny), but they can serve a purpose.

In this post, I’m wearing an older pair, but these look really similar.

  • Crop Flare Jeans

Similar to bootcut jeans and how they flare at the end, but these are shorter (cropped) and are a more current version. You may also see these go by demi-boot, crop flared, flare cropped, etc.

In this post, I’m wearing an older pair, but these look really similar.

  • Wide Leg

Instead of flaring out at the end, these have more of a general roomier fit on the legs, while still being fitted around the waist and hips. They are not supposed to be baggy.

In this post, I’m wearing Everlane’s Way High Jean. They are technically not wide-leg jeans, but that is how they fit on me. However, here is their version of a true wide-leg jean.

When building your jean collection, stick with denim jeans of varying washes. Blue jeans are going to be the most classic and it’s helpful to have them in a light, medium, and dark wash to cover different seasons and occasions.

Once you’ve got those covered, black and white are the next helpful and classic colors to have. Regarding what’s trendy, different colors will always come in and out in popularity, but neutral ones are the best ones to have first.

Now, onto the boots:

what boots to wear with jeans
  • Ankle Boots

Ankle boots, ankle booties, calf boots-these are all used interchangeably by retailers and stylists alike, but there are slight differences. For this post, we are classifying ankle boots as boots that end at the ankle (sometimes called a bootie).

In this post, I’m wearing Everlane’s The Day Boot. These ankle boots are an investment and they cost more now than what I paid for them, but I think they’re worth every penny. I’ve worn these for years and they are my favorite pair of black boots. They’re about as classic as you can get.

  • Calf Boots

Sometimes calf boots fall under the ankle boot umbrella. But these taller boots have a higher shaft, so to differentiate for the sake of this post, I’m calling them calf/mid-calf boots as sometimes they’re advertised as mid-calf boots too.

In this post, the ones I’m wearing are old, but these look really similar.

  • Knee-High Boots

This style of boot is a classic and will never be out in my opinion, though lately, cowboy boots have taken their place. Western boots don’t make the timeless fashion cut to me, but if you have a pair you’re trying to style, these tips can be shared, assuming your cowboy boots are tall boots. Though the styles are different, the shaft of the boot usually fits the same as wider knee-high boots.

In this post, the ones I’m wearing are old, but these look really similar.

  • Knee-High Lug Sole Boots

These have more of a casual look and though they’re not as timeless, I’ve included them because they’ve been around for a few years and I think they’ll be around for a while. (And living in the midwest, I wear mine a lot and I think they’re a really practical yet stylish shoe).

In this post, I’m wearing Sam Edelman’s Waterproof Platform Boot.

  • Sock Boots

Sock boots aren’t what’s “in” right now (if that matters to you), but I think they’re one of the best boots to wear with almost all types of jeans. Because they fit like a sock, they take a lot of the guesswork out of knowing what jeans to pair with them. As long as the jeans have a wider-leg opening than the sock boots, you’re good to go.

In this post, I’m wearing Everlane’s Knit Boot and I highly recommend them!

  • Chelsea Boots

This is a classic style that has seen a lot of reiterations. If you have a taller pair, then the height is similar to combat boots and these tips could work for those as well.

In this post, I’m wearing Sam Edelman’s Laguna Chelsea Boot.

As you start to build your boot collection, make sure you get different colors. No, not pink, orange, or purple, but brown, black, and varying shades of beige. You’ll find that you can wear and style these colors the most. Then if you want to get a few fun colors and prints, feel free!

Related: How to Flawlessly Execute a Jeans and Boots Outfit

Okay, now that you’ve got the shoe and jean overview, let’s get technical, technical.


straight leg jeans with ankle boots

Starting with my favorite pair of jeans, straight-leg, let’s see what works. As you can see, the majority of the classic boot styles work, which is why this is one of the best styles of jeans to have in your wardrobe.

They are a great option to wear with almost every major boot style, but one style specifically doesn’t work as well: knee-high boots. If you’re wearing taller boots over bottoms, then it should have a seamless fit. Straight/slim jeans are not skinny, tight, or fitted enough.


how to wear crop flare jeans

Crop flare jeans are probably the second best option to wear if you’re wondering how to wear ankle boots with jeans. As you can see, most shoe styles work, except once again, taller boots do not.

Because crop flare jeans have a flare and not a wide leg, there is not enough room to wear tall boots under and they are not seamless enough to wear over. Both scenarios create weird lines, bulges, and unnecessary bulkiness.

When it comes to pairing this jean style with ankle boots, the best way to ensure that it looks good and not awkward is to keep the hem of your jeans 1/2 inch to 1 inch (ideally) above your jeans, measuring at the top of the booties.

Any lower than a 1/2 inch and your jeans could start to get stuck in your pair of ankle boots. Any higher than 2 inches and the proportions look off, almost like you are wearing capris with boots.

how to wear ankle boots with jeans

To sum up: A good rule of thumb for crop flares and ankle boots is that your jeans slightly graze your boots by 1/2 inch OR the jeans hang past your boots.


how to wear ankle boots with jeans

Currently, I rarely wear skinny jeans, and if I did, it would be with knee-high boots. But if you still wanted to wear your skinny jeans with ankle boots, you have some different options. Depending on how long your skinny jeans are, you may need to find a way to make the meeting of jean and boot aesthetically pleasing.


  • Tuck your skinny jeans into your boots
  • Fold the skinny jeans under to create a cleaner break
  • Single cuff

Cuffing them is my least personal favorite option as I think it’s dated and it reminds me of this girl:

outdated style
Only making fun of MYSELF here, by the way 🙂

If your jeans will stay, I think folding the jeans under can be a great way to still wear this jean style if that’s what you want.


how to wear ankle boots with jeans

Because wide-leg jeans have a wider leg opening, it makes wearing ankle boots a lot easier! With this jean style, your boots need to go under without being too tall. Be careful of ankle boots/ booties as you don’t want the jeans “meeting” the boots because they can get stuck when you walk.

We covered a lot of dos and don’ts. In a nutshell, here’s what I think doesn’t work:

how to wear ankle boots with jeans

And here are visual examples of what does:

And if you need an easy graphic to pin without my face in it (aww why not), then just tap the picture if you’re on mobile:

That’s a lot! Let’s summarize:

  • The easiest (and most current) way to wear ankle boots with jeans is the following jean styles: Straight leg jeans, crop flare jeans, or wide-leg jeans.
  • My favorite way to wear ankle boots with jeans? If I had to pick, I’d choose the combination below, but it’s certainly not my only favorite:
    Perfect straight jeans from Madewell + Everlane ankle boots or Everlane sock boots
    (But I also love calf boots ahh can’t pick)
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The fall and winter season is the perfect time of year to wear ankle boots with jeans. Now that you have these tips and you’re well on your way to mastering this style, next up: outfit ideas!

Up Next: The Best Shoes To Wear With Jeans? Get Inspired by These 4 Sock Boot Outfits

how to wear boots with jeans
how to wear ankle boots with jeans


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.