Ankle boots and straight jeans

How to Easily Wear Ankle Boots with Straight Leg Jeans

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I discovered straight leg jeans after the pandemic. After months of wearing leggings and sweatpants, the ankles of my skinny jeans felt way too tight. So I went on the hunt for a super comfortable pair of jeans.

Around that time, TikTok declared skinny jeans to be uncool. I’m not one to blindly follow trends (after all, this blog is called Be So You for a reason!). And I firmly believe that skinny jeans will remain in closets because they’re so flattering on so many body types. But I was ready to find more comfy jeans and freshen up my look. 

Today, straight leg jeans are the one style of jeans I wear day in and day out. 

Why? Once you get the hang of them, they’re easier to wear with a pair of ankle boots than skinny jeans. And they work with a wide variety of shoes and across all seasons. 

With that said, I know many people struggle to find the right combination of ankle boots and straight jeans since tall boots aren’t an option to wear with straight jeans. 

If you are having trouble figuring out how to wear your straight jeans with ankle boots, I’m here to be your style guide. Help is on the way!

First, if you’re struggling, it’s important to know that there are different styles of straight jeans. And this will make a difference in how easily you pair them with ankle boots.

There are true straight jeans and also tapered straight jeans. Plus, cropped and cropped flare jeans. 

Let’s just focus on true straight and tapered straight jeans for a sec. 

A true straight jean is straight from the knee down. 

You can check to see if the leg of your pair of jeans is straight by folding the hem up to the knee. There should be no difference in width between the two. 

If the ankle is narrower than the knee, you have a pair of tapered straight jeans. They fit like loose skinny jeans at the ankle.

Sometimes, when you’re ordering your straight jeans online, it’s hard to know what you’re getting. The jeans will be called straight jeans. But the fine print of the description says they’re tapered straight jeans. This detail makes a difference for pairing them with ankle boots.  

The length also makes a difference. If you order a regular length tapered jean and they hit at the top of your foot, they may be too tight at the ankle to wear down over the top of an ankle boot. Like skinny jeans, you’ll need to cuff them up, cuff them under, or cut them off to make them work. 

If you’re not into cuffing or cutting your jeans, which makes a more casual look, there are tight sock boots, which go under the hem of the jeans. Sock booties are made of a stretchy material that hugs the ankle tightly like a sock. I wish I loved them more. They just don’t feel like me. So I had to look for another option. 

The best option I’ve found is to buy jeans that are ankle length. 

I happen to love the Audrey Hepburn inspired ankle length pants look. So I like to buy my straight jeans in short lengths or cropped lengths. That way, at 5’6”, they end around my ankle. Or a little above it. But not capri length, which ends higher on the calf and cuts off the leg line making you look shorter.  

Ankle boots are so much easier to wear with ankle length jeans. The shaft of the boot fits right up under the top of the ankle length or cropped jeans. Whether they’re tapered or true straight jeans. 

This is especially helpful since today we’re seeing more higher shaft ankle boots. And fewer ankle booties with lower shafts. 

Let’s talk about the shaft of an ankle boot for a second. There are 3 general shaft heights: short, medium and high. A short shaft is an ankle bootie and it’s around 3 inches from the top of the heel to the top of the boot. A medium shaft is around 5 inches, stopping just above the ankle. And a high shaft is 6 inches or more. 

The tighter your ankle boot shaft fits around your ankle, the easier it’ll be to make them work with straight jeans. 

The most versatile pair of straight jeans is ankle length or cropped. Whether they’re tapered or true straight, they work with just about any shaft height. 

If you have a pair of jeans that are tapered and longer than ankle length, don’t worry, there’s a solution. You’ll treat them like skinny jeans and cuff them up, cuff them under, or cut them off for a more casual look. Follow the instructions in my skinny jeans post for your straight longer jeans

Now that you know about the different styles of straight leg jeans and the shaft heights, let’s look at some outfit ideas so you can see how to wear ankle boots with straight leg jeans. 

Ways to wear ankle boots with straight-leg jeans

There are a few general guidelines to know when wearing ankle boots with straight jeans. These aren’t hard and fast rules because, with fashion, anything goes. And what’s more important than following trends or rules, is to dress in a way that’s most flattering to your body. But once you know the guidelines, you can intentionally adapt them to make them work for you.

Here are 5 scenarios that work for wearing ankle boots with straight-leg jeans.

Scenario 1: The hem of your jeans stops just above the top of your boots. Having the hem of your jeans stop just above the top of your boots is a great way to wear them. You want to allow just a sliver of skin to show. And avoid having the hem of your jeans show more than 2 inches of skin. Since super short jeans look like high water jeans. Plus, the length of your jeans impacts how long your legs look. Creating the appearance of a longer leg line by wearing longer jeans is always a good idea. 

This is an easier look to create with cropped jeans. Here I’m wearing a pair of straight cropped jeans with a medium shaft ankle boot. 

Ankle boots with straight jeans
Cropped Straight Jeans

See how you can just see a sliver of skin above the top of the boot? 

In this next image, I’m wearing a pair of crop flare jeans in white, also from the Gap. With the same pair of ankle boots. They stop right at the top of them. 

Ankle boots straight cropped flare jeans
Crop Flared Jeans

If you’re wearing socks, it’s fine to let the top of your socks peek out from the top of the boot. 

Scenario 2: The hem of your jeans comes down over the shaft of the boot, stopping above the ankle of the boot.

This is a look that may happen with cropped wide-leg jeans or cropped flared jeans, depending on the length of the inseam. The hem of the jeans easily fits down over the top of the ankle boot. This is my favorite way to wear them. Because it works with so many different ankle boots. 

The first pair of jeans here are called cropped wide leg jeans, although the jeans are actually straight from the knee to the ankle. 

wide-leg jeans with brown ankle boots
Crop Wide-Leg Jeans

These brown boots have a very long toe box, which helps to lengthen the leg line. A pointed toe boot does the same thing. But I haven’t found a pair of pointy toe ankle boots I love yet. These feel more like me. 

This next outfit combo is with crop flare jeans from the Loft. They kick out a bit at the ankle and stop right above the ankle of the boot. Since I’m larger on the bottom (a size 12), I love how a crop flare works for my body type to balance the width of my hips and tushie. I also love bootcut jeans for the same reason. 

crop flare jeans
Crop Flare Jeans

In this next picture, I’m wearing black jeans that are cropped and flared, with a pair of black platform Chelsea boots. If it feels like you, you could also do this look with a pair of pointy toe stiletto heel ankle boots for a chic look. Or a pair Doc Martens combat boots for an edgier look. Throw a leather jacket over top to complete the look.

crop flare black jeans
Crop Flare Jeans

If you want to extend your leg line, match your boots to the color of your jeans to create a long column of the same color.

Scenario 3: The hem of your jeans comes down over the shaft of the boot, stopping at the ankle of the boot.

With this scenario, the inseam of your jeans is longer than with cropped jeans. In the next two looks, I’m wearing tapered short length jeans. At 5’6”, that’s the length I need to make this look work. 

In this picture, I’m wearing Classic Straight Levi’s jeans in the short length with a pair of flat ankle boots. Technically, they’re a pair of classic Chelsea boots. 

They have a medium shaft ankle boot. See how the jeans are longer and stop at the ankle of the boot?

straight tapered short jeans with ankle boots
Tapered Straight Short Length Jeans

This look works well with many ankle boots except for one. And that’s an ankle boot with a tab on the back. You may find that the hem of your jeans gets caught up on the tab. 

This next picture is a pair of tapered Old Navy straight jeans in a short length. They also stop at the ankle of the boot.

straight short tapered jeans
Tapered Straight Short Length Jeans

If you do a side by side comparison of all the jean types so far, my legs look longest in these jeans. 

Scenario 4: Have the hem of your jeans come down to the top of the toe box. 

The jeans I’m wearing here are technically full length mom jeans. They have a very high waist and fall straight down from the knee to the ankle.

mom jeans
Mom Jeans

These are easy to wear with a variety of ankle boots. Since they easily pull down over top of them. 

Scenario 5: Try them with sock booties or treat your tapered straight jeans like skinny jeans. If your slim fitting straight jeans are longer and come down to the top of the toe box, try them with sock booties, if they feel like you. Or you can cuff them up, cuff them under or cut them off to make them work. Follow the instructions in my skinny jeans post for your straight longer jeans

Cuffing them up, you may find you have to roll them several times. A narrower roll is preferable to a wider roll. Since a wider roll will cut off the leg line. 

I tried my pair with a higher shaft ankle bootie. And I had to roll them 3 times and they still bunched at the top of the boot. 

The best way I’ve found to wear them is with a pair of ankle booties that have a lower shaft. I prefer one with a heel because it looks more current. 

regular length tapered straight jeans
Tapered Regular Length Straight Jeans

With a low shaft ankle bootie, I rolled them 2 times, exposing my ankle bone. Exposing the ankle bone lengthens the look of your legs. 

If you’re going to roll your jeans, you want the cuff to stop at the top of the boot. When the cuff comes down over the top of the shaft of the boot, you risk looking frumpy. 

How to wear ankle boots with straight jeans

Wear your ankle-length straight jeans so the hem comes to the top of the boot. Or let the hem come down over the top of the boot. If you’re having trouble pairing your straight jeans with ankle boots, it may be that your straight jeans are tapered. If they come down to the top of your foot, try them with sock booties, if they feel like you. Or treat them like skinny jeans and cuff them up or under, or cut them off. 

Try different combinations of straight jeans and ankle boots and take pictures of yourself in the mirror wearing them. It may take some trial and error. And you may need to return pieces that don’t work. But you will get there! I’m rooting for you to find a combination you feel great wearing! XO, Marya

ANKLE BOOTS POSTS YOU MAY LIKE:

22 Easy Outfits: How to Wear Ankle Boots Over 40

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

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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