Ankle boots with straight jeans

How to Wear Ankle Boots + Booties With Jeans (10 Looks)

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Ankle boots have become a wardrobe staple! They’re perfect for pairing with any ankle length jeans like skinny jeans, straight leg jeans, and wide leg jeans that are cropped. And also, longer styles like mom, bootcut and flare jeans. 

If you’ve found a pair of boots and jeans that you really love, it’s a bummer to get them home and find out they don’t work together. 

Today, I want to go through the jeans and ankle boots that work with one another, so you can figure out the best boots and jeans for you, and easily make outfits that you feel good wearing. I also have 10 outfit ideas for you.

By the way, I also have posts on how to wear ankle boots with skinny jeans, and flat ankle boots with jeans. You can check those out to go deeper:

How to Wear Ankle Boots with Skinny Jeans + 8 Looks

19 Flattering Ways to Wear Flat Ankle Boots With Jeans

Some of this post will cover a bit of the same information, but it’s useful to have it all in one place for easy reference. 

There are several different types of ankle boots and the type you choose depends on the style of jeans you plan to wear. 

When you’re styling jeans and ankle boot outfits, the goal is to keep your legs looking long. 

Almost every body type benefits from making your legs look longer. If you’re curvy or larger on the bottom like me (size 12 here!), that naturally makes your legs look shorter. 

Once you know the basic strategies for making your legs look longer, you can intentionally break those rules to express your personal sense of style. After all, stylish looks are created all the time by breaking style rules on purpose. 

First, let’s talk about the different types of ankle boots because there are important differences that can impact how happy you are with your overall look. 

Then, we’ll go into the types of jeans and the ankle boots that work best with them. 

Types of ankle boots

Ankle boots have 4 characteristics that you want to keep in mind: shaft height, toe shape, color and heel height. 

The first is shaft height.

Shaft height. The shaft of the boot is the part that goes from the calf or ankle down to the top of the heel.  

There are 3 general shaft heights. Low, medium and high. 

When an ankle boot has a low shaft of about 3 inches, that’s called a bootie. Often times, we use the term ankle boot and bootie interchangeably. But technically, a bootie has a short shaft and the ankle may be exposed. Exposing the ankle in a low shaft bootie is one way to make the leg line look long.  

A medium shaft is around 5 inches and hits just above the ankle. 6 inches and above is a high shaft ankle boot.

Toe shape. You also want to consider toe shape. There are round, square, almond and pointed toe boots. The boots that lengthen the leg line have almond, round (with a long toe box), and pointed toes.

Boot color. Ankle boots come in many different colors. They may be white, tan or taupe, or brown or black. Choosing a boot that matches your skin color can lengthen the appearance of your legs. Pairing black booties or ankle boots with black jeans also creates one solid long leg line.  

Heel height. Your ankle boots vary from flat to less than an inch, to heels of 2 to 3 inches. Wearing a heel will obviously give you more height and lengthen your legs. 

ankle boots and booties

How to wear ankle boots with jeans 2022

You may be wondering if ankle boots are still in style in 2022 and heading into 2023. And the answer is, yes! Today, ankle boots are leaning towards having a higher shaft and a heel for a fresher look. To make a higher shaft work with your jeans, your jeans need to either be ankle length to hit at the top of the boot, or have a wide enough hem to fit down over top of them. Lug sole and classic style Chelsea boots (including rubber Chelsea rain boots), combat boots, and Western inspired ankle boots that resemble cowboy boots are all trending right now. Flat ankle booties with a low shaft look a bit stale.

Ankle boots work with ankle length jeans and are also a great option with longer jeans like flare, bootcut and mom jeans.

Now let’s look at the jean types that work with different ankle boot types, starting with skinny jeans. 

How to wear ankle boots + booties with skinny jeans 

TikTok declared that skinny jeans are over, but for many people, skinny jeans are the most flattering jeans to wear. Skinny jeans are still the best way to show off your knee-high boots or cowboy boots over a pair of jeans.

The easiest way to create a long leg line is to wear them with shorter shaft ankle booties. That way you don’t have to cuff or fold under the hem of your jeans, so you keep the leg of the jeans smooth and long. 

Can you wear taller ankle boots with them for a new look? Yes! That will require you to cuff them or tuck them under. If you cuff them, cuff them once or twice, making the slimmest cuff possible, since a wider cuff cuts off the leg line. Tucking them under gives you an even cleaner leg line. You can see how to tuck under your jeans in this video on Pinterest

As a general rule, you want the hem of the jeans to come just above the top of your boots. With shorter ankle booties, revealing the ankle lengthens the leg line. With a taller pair of ankle boots, it’s a good idea to show only a sliver of skin. That allows you to keep the jean length as long as possible to keep the leg line looking long.

Here’s a side by side of skinny jeans with a short ankle bootie where no cuffing is needed. Plus, a medium shaft ankle boot that’s cuffed, and a higher shaft ankle boot that’s tucked under. 

Side by side pictures, how to wear ankle boots and booties with skinny jeans

See how the legs look longest with the low shaft ankle bootie? It also helps that they have a 2.5-inch heel. It adds height and the tan color matches my skin tone making my legs look longer. And I’m half-tucking my shirt to show my waist. 

We’ve seen a lot of flat ankle booties over the years so they feel a bit stale these days. To create a fresher look, try a bootie with a heel, if you can wear them. Wearing current shirts and tops is a great way to keep your look modern. I’m wearing an oversized white button down. It’s a classic that’s trending.

I wrote a whole post about how to wear ankle boots and skinny jeans. If you want more pictures, tips and strategies, read How to Wear Ankle Boots with Skinny Jeans + 8 Looks

Next up, let’s talk about straight jeans. 

Straight jeans are a more comfortable alternative to ankle hugging skinny jeans. Let’s see how to wear them.

How to wear ankle boots with straight leg jeans

Straight leg jeans come in cropped, ankle and longer lengths. 

They get their name because true straight-leg jeans keep the width of the knee all the way to the hem at the ankle. 

However, some straight-leg jeans are very slim fitting and tapered, fitting more like a loose skinny jean at the ankle. 

If you are having trouble making your straight jeans work with ankle boots, it’s possible they’re tapered straight jeans. To check and see if your jeans are tapered, fold the hem up to the knee. The ankle should be the same width as the knee and should stay that width all the way down. 

How to Wear Tapered Straight Jeans with Ankle Boots

If they’re tapered and stop at the ankle, you can just let them come down over the top of the booties or boot like I’ve done in the next picture. I’ll talk more about this in a minute. 

tapered ankle length straight jeans

If they’re tapered and so long that they hit the top of your foot, style them like skinny jeans and cuff them or fold them under. I experimented with pulling the hem down over very tight shaft ankle boots. I didn’t love that look. Sock booties are meant for this purpose. But I don’t like them and how they look with jeans.

I prefer to wear long tapered straight jeans with a low shaft bootie with a heel. And to cuff them twice. This makes the cleanest and longest line for the leg. 

long straight tapered jeans

I tried them with a higher shaft ankle boot and I had to roll them 3 times and the cuff was still all bunched up around the top of the boot. 

These are not my favorite jeans because they’re tapered and so long. If you have the same problem, the best option is to buy true straight jeans. If they’re wider at the hem and ankle length or longer, you don’t have to deal with rolling them and can more easily wear all your ankle boots with them. 

Now let’s talk about ankle length straight and cropped jeans. 

How to Wear Ankle Length Straight + Cropped Jeans with Ankle Boots

The jeans that are the easiest to style hit at the ankle or above. They may be tapered, true straight leg jeans, kick crop flare jeans, or cropped wide leg jeans. The hem of the jeans fits down over top of the ankle boot. This is my favorite way to wear them because they’re so versatile and you can wear them with all different ankle boots. 

Here, I’m wearing tapered short straight jeans pulled down over the shaft of a flat classic brown Chelsea boot.

ankle length tapered straight jeans

The hem goes down easily over the shaft and hits right at the top of the ankle.

Next, I’m wearing a pair of cropped straight jeans. The hem of the jeans hits right above the top of the ankle boot.

cropped straight jeans

For your cropped jeans, there are a few different ways to wear them. It’s fine for them to hit above the top of the boot showing a sliver of skin. Or below the top of the boot allowing the ankle of the boot to show. And longer, hitting the top of the toe box. 

Here’s a pair of black crop jeans that have a flare to the legs. The jeans come down over the top of the ankle boots by an inch or so.

black flare cropped jeans

See how wearing black boots with black jeans lengthens the leg line?

In the next look, I’m wearing another pair of cropped flare jeans.

flare cropped jeans

The jeans come down over the top of the ankle boots by a few inches.

Next, I’m wearing wide leg cropped jeans and the hem is just above the top of the boot.

wide leg cropped jeans

These show only a sliver of skin. The higher the jean stops above the top of the boot, the shorter your legs will look. If it’s over 2 inches, you risk looking like you’re wearing high water jeans. 

Infographic: how to wear ankle boots and booties with straight and cropped jeans

Now let’s talk about how to wear ankle boots with longer jeans like mom, bootcut and flare jeans. 

How to wear mom, bootcut and flare jeans with ankle boots

There are some differences between mom, bootcut and flare jeans.

Mom jeans are straight from the knee down like straight jeans. Mom jeans that come to the top of your foot are easy to style with a variety of ankle boots. Here, I’m wearing them with a pair of lug sole platform Chelsea boots.

mom jeans

Mom jeans are all about comfort in the hips and midsection. The hem comes to the top of the foot and is a straight cut making them so easy to style. Any ankle boot works with them.

Bootcut jeans have a slight flare from the knee down. This flare allows space for a tall boot to fit underneath, hence the name. This is one of my favorite styles to wear because it makes your legs look so long. 

bootcut jeans

The hem of bootcut jeans comes down to the top of the toe box.

With both styles of jeans, you may be able to wear them with both a flat and a heeled boot. 

Now, flare jeans are trickier to style since they have a bell that begins about 2 inches below the knee. And they are intentionally 2 to 3 inches longer.

flare jeans

They’re meant to almost touch the ground. I don’t know about you, but I’m not thrilled about my jeans dragging on the ground. I prefer them with an ankle boot with a heel that allows the flares to be off the ground by a couple of inches.

You want to choose a boot with a long toe box so the shoe sticks out from underneath the hem. If you want to wear them with flat shoes, buy your flares in a short length so you don’t have to get them tailored and lose some of the bell of the flare. 

Infographic: How to wear ankle boots and booties with mom, bootcut and flare jeans

How should jeans be worn with booties and ankle boots?

Booties and ankle boots are terms we use interchangeably. But technically, booties have a lower shaft and stop around the ankle. And ankle boots stop above the ankle. Today we’re seeing higher shaft ankle boots with heels or lug soles. They work perfectly with ankle length jeans that are true straight jeans or that are cropped or flared, or that have a longer and wider leg like a mom, bootcut or flare jean. 

There are so many options in the stores today for boots and jeans. It may take some trial and error to come up with the right boot and jeans combinations. I am rooting for you to find the look that you feel great in! XO, Marya


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Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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