22 Easy Outfits: How to Wear Ankle Boots Over 40

This post contains affiliate links to products, apps, and/or services. As an Amazon Associate, I earn from qualifying purchases. If you click through and purchase, I will receive a small commission on the sale at no additional cost to you. Clicking on a link does not result in a commission. I only recommend products or services that I personally use or believe will be helpful to my readers.

Check out what’s in this post

You bought a pair of ankle boots, but now you have questions about what you can wear with them. I have been there! It always takes a period of trial and error to figure out what works when you introduce a new item to your closet. The good news is that just about anything goes with ankle boots these days.

What can you wear with ankle boots? 

You can wear ankle boots with jeans and ankle, trouser and wide leg pants. They add a fresh look to skirt and dress outfits.  And you can wear them with tights and hose. But there are some general style guidelines to keep in mind. Once you learn them, you can play with the rules to make outfits that express your sense of style. And wear them in a way that feels good to you. 

After returning a lot of ankle boots, I’ve studied what makes a pair work. I’m here to be your style guide as you discover all the ways you can wear these boots.

In this post, I show you what to look for in an ankle boot. And also how to style them with blue jeans, dresses, skirts and pants. 

But first, there are some differences between styles of ankle boots that are important to know. When you understand them, it’ll be easier to put together a look you love. 

Let’s quickly talk about the types of ankle boots. 

Types of ankle boots

When you’re considering the type of boot to buy, there are 5 things to think about. Shaft height, heel height, toe shape, color and boot material. 

The shaft is the part of the boot that extends from the top of the heel to the top of the boot, measured up the back of the boot.

Shaft of a boot infographic

An ankle boot is designed with a shaft that ends around the ankle rather than at the knee.

Shaft height. There are 3 general shaft heights on your ankle boots. A low shaft, which exposes the ankle bone. Around 3 inches high. Technically, these are known as ankle booties. They’re perfect for skinny jeans. And also cute with midi and maxi dresses. A medium shaft, which hits a couple of inches above the ankle, measuring around 5 inches. We’re seeing lug sole and classic Chelsea boots with a medium high shaft. Your cropped jeans and pants hit right at the top of a medium high shaft boot. Last, high ankle boots have around a 6-inch shaft or higher. They extend above the ankle by a few inches. And are worn up under your jeans or pants hem.  There are high shaft boots that lace up too. Remember Doc Martens? They resemble a pair of combat boots and have a high 6 and a half inch shaft. 

Heel height. Heel height determines if your outfit looks more casual or dressy. You’ve got flat boots, lower and higher chunky heels, platform boots, stiletto heels and high heels as options. The ankle boot heel height you should buy is the heel height you’ll actually wear based on your height and lifestyle. While stilettos and high heels make your legs look longer, if you’re going to be tortured by them, they’re not worth it. Remember when Monica on Friends buys a pricey pair of pointy toe stiletto heel boots and can’t walk in them? 

Toe shape. Toe shape impacts how long your legs look. Pointed toe boots are one of the best shapes to elongate your legs. But if your feet don’t love them, try an almond shape or round toe with a long toe box. 

Boot color. You can use boot color to make your legs look longer. A boot that matches your skin tone extends your leg line. You can also match your pants or skirt to your boots to make your legs appear longer. So wearing black boots with black pants or skirts lengthens your legs. You’ll find white ankle boots, taupe, brown and black boots in the stores. 

Boot material. The boot material and whether it’s suede or shiny or matte can determine how fancy a boot looks. For example, suede tan booties create a more casual look and shiny black boots can be dressed up with a pair of trouser pants or skirt because of their shine. 

Wear what feels like you and works for your style sensibilities. For example, despite how great pointed toe ankle boots are for elongating the leg, I haven’t found a pair that feel right on me yet. So I don’t own a single pair of them. I prefer almond toe or round toe with a long toe box for their comfort and how they look. 

I’m sharing some general guidelines as a starting point. Take what tips work for you and then leave the rest behind. This website is called Be So You to empower you to wear what makes you feel great.

First up, let’s talk about how to wear jeans with ankle boots.

Can you wear ankle boots with jeans? 

Absolutely! You can wear a pair of ankle boots with a pair of jeans. But there are certain ankle boot styles that work better with different styles of jeans. 

There are so many different jean styles on the scene right now.

If you’re worried skinny jeans are out of date, they will always have a place in closets because they’re so flattering to so many body types. They are also the best jeans to wear with tall boots. A close cousin of the skinny jean is the straight jean. They have a slim fit in the tushie and a straight cut from the knee down. And they work great with ankle boots because they are wider at the ankle.

Let me give you a quick summary of the key tips to keep in mind when pairing ankle boots with ankle-length, cropped and longer jeans. 

Ankle-length and cropped jeans. If you’re wearing cropped, skinny, wide leg, flare or straight leg jeans that hit at or above your ankle, a general rule is to have the top of your jeans hit just above or at the top of the boot. So when you move, a sliver of skin shows. 

wide leg crop jeans
Wide Leg Crop Jeans
Ankle boots with straight jeans
Straight Crop Jeans

This length shows off the boot. You’re trying to avoid having too much distance between the hem and top of the boot, which creates a high water effect. And shortens the look of your legs.

If you want to wear skinny jeans that have a tight ankle hem with a higher shaft ankle boot, you’ll need to cuff them or tuck them under. So this post isn’t 4,000 words long, I’ll refer you to my post How to Wear Ankle Boots with Skinny Jeans + 8 Looks to learn how to cuff them. I give you tips about how to do it and show you lots of pictures. 

If your cropped or ankle-length jeans fall below the top of the boot, that works too. 

tapered straight jeans
Tapered Short Straight Jeans
tapered straight jeans
Tapered Short Straight Jeans
flare crop jeans
Flare Crop Jeans

Now, some straight-leg jeans are tapered at the ankle, fitting like looser skinny jeans. If they’re short like in this first and second picture, they can easily come down over the top of the boot. For reference, I’m 5’6″ tall. If they’re long, you have to cuff them with ankle boots. I show you how to cuff them in my post, How to Wear Ankle Boots + Booties With Jeans (10 Looks)

Long mom, bootcut and flare jeans. For a jean that’s longer, like a mom, bootcut or flare jean, if your jeans come down to the top of the toe box, this is very easy to style. You can wear any shaft height. You want to choose an ankle boot with a long toe box so the boot shows under the jeans and continues the leg line even longer. 

mom jeans
Mom Jeans

For mom and bootcut jeans, you may find that both flat and heeled ankle boots work with the length of your jeans. 

bootcut jeans
Bootcut Jeans

Flare jeans are meant to be worn longer and most average height women will need to wear a heel of several inches to keep them from dragging on the ground. 

flare jeans
Flare Jeans

It may take some trial and error to find the right pair of ankle boots to go with your favorite pair of jeans. Take mirror selfies of yourself in the outfits so you can see how a combination works. And give yourself some time to try many styles to find a pair you really love. 


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

19 Flattering Ways to Wear Flat Ankle Boots With Jeans

How to Wear Ankle Boots with Skinny Jeans + 8 Looks

Ready to move on to talking about dresses and skirts? Let’s do it!

Are ankle boots okay with a skirt or dress?

Ankle boots are a stylish option to pair with a skirt or dress. While a tall knee high boot always creates a classic look, an ankle boot creates a fresh look! 

Here are some easy tips to help you get started with trying on outfit combinations. 

Choose a boot that matches the color of the dress or skirt to create a seamless line. So wear a black skirt or dress with a black ankle boot like I’m doing in the first and second pictures below.

sweater dress and ankle boots
sweater dress and ankle boots

If you’re wearing black boots with a colored dress or skirt, wearing black hose or tights creates a long column of legs.

flannel dress and ankle boots

If you’re wearing bare legs, choose a skin-tone matching ankle boot to elongate the legs.

dress and ankle boots

The taupe low-shaft pair of booties in this picture hits a fun note. This is a look you can wear going from winter to spring. And from summer to fall. It also works for summer months with cool evenings. Swap out the denim jacket for a short trench coat for an easy breezy look.

Choose an ankle boot shaft height that hits lower down at the slimmest part of your ankle. And an ankle boot that’s fitted tight around the ankle. A loose boot makes legs look frumpy.

red flannel dress and ankle boots

Be careful with a shaft that hits at a higher thicker spot on your leg because it will cut the leg line creating a shortening effect. 

Here’s another look that works because the ankle boot fits tight around the ankle.

This brown ankle boot has a chunkier heel that works with this flowy skirt.

green clip dot dress outfit

If you have a shorter mini skirt, choose a taller boot like a knee-high boot, especially if you’re going into a professional setting.

For a maxi or midi skirt, you can go for a higher shaft ankle boot like in the next picture.

maxi skirt outfit
Maxi Skirt

Or an ankle-exposing low-shaft heeled bootie. This is a more casual look.

maxi skirt and taupe ankle boot
Maxi Skirt

Next, I’m wearing a midi skirt with a low-shaft taupe bootie because the taupe is a better match for the color of the skirt.

Midi skirt and taupe boot
Midi Skirt

Both of those ankle boots also work with a knee length or pencil skirt.

black ankle boot and knee length skirt
taupe ankle boot and knee length skirt

If you are full figure and have curvy legs, follow Paula Holloway’s advice and choose ankle boots with a notch or V at the front to elongate the look of your legs.

Can you wear socks with ankle boots?

If you live in a warmer climate, you may be comfortable in lower shaft ankle booties wearing just a pair of low-cut socks that won’t show with the boot.

If you need to be warmer in your ankle boots, choose an ankle boot with a higher shaft so you can wear ankle socks that stay hidden. You can also match the socks to the boots and have them peek out over the top of the boot for a more casual look.


Let’s move on and look at pants, shall we? 

How to wear ankle boots with pants

Wear ankle boots with ankle length pants the same way you’d wear them with ankle length jeans. 

Have your pants stop just above the top of the boot. Or pull the hem of the pants down over the shaft of the boot like I’ve done here.

black chinos and ankle boots

For pants that just come down over the top of the boot, they still show off the ankle of the boot. 

It’s easiest to style ankle pants that have the width to come down over the top of the boot. That allows you to wear them with a variety of higher shaft ankle boots. Although, you can also cuff the hem of the pants if you need to. 

With wide leg trousers, choose an ankle boot with a long toe box.

navy wide leg trouser pants outfit

I love finding boots with a very long toe box so I get the leg lengthening effect without having to wear a pointed toe. That makes them comfortable and a good match for a variety of different styles of pants. 

In the next picture, I’m wearing black trouser pants with an oversized sweater and I’m matching the color of the pants with the color of the boots so the legs look even longer.

black trousers outfit

Black on black creates one long leg line.

What are the most versatile ankle boots to have in your closet? 

If you plan to wear your ankle boots with bare skin, the most versatile pair of ankle boots matches your skin tone. It will also pair well with a variety of different colors of jeans, pants and skirts. 

A lower shaft ankle bootie is a great option if you wear a lot of skinny, slim fitting or tapered ankle length straight pants and jeans. Then your pants will fit over top of them without you needing to cuff them. 

A medium or high shaft ankle boot works well with cropped jeans and pants. 

If you wear a lot of black bottoms or plan to wear black hose with dresses and skirts, choose a pair of ankle hugging low or medium shaft black ankle boots. They create a sleek, long line. 

Choose the toe shape and heel height that you feel great in and that you’ll actually wear.

When you’re trying ankle boots for the first time, start with an inexpensive pair. Wear them around and make outfits with them to see all the different ways you will actually wear them. Testing them out is a great way to see what you like and need in an ankle boot. Then spend more on a pair based on what you’ve learned.

I’m rooting for you to find your perfect pair! And if you have a question or comment about something I didn’t cover, just leave it below. 



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.

You might also like...

Leave a Reply

Your email address will not be published. Required fields are marked *

Free Download - Human Design for Midlife Women

Get the Quickstart Guide to Human Design for Midlife Women

Short Description

Your privacy is important to me. That’s why I collect, use, and process your personal data only in accordance with my Privacy Policy. You may unsubscribe at any time.