White blouse and platform Chelsea Boots and black chain purse

How to Wear Ankle Boots with Skinny Jeans + 8 Looks

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Skinny jeans have been a closet staple for over 10 years. And they are here to stay.

Perhaps you heard that Gen Z said on TikTok that skinny jeans are uncool.

But Stacy London, style expert and former host of What Not to Wear. And the CEO of Levi Strauss & Co predict they will remain in closets.

These jeans may see a rise or drop in popularity from time to time. But for many people, they are the most flattering jeans to wear and will stay a staple piece of their wardrobes. 

There are lots of reasons to love skinny jeans. 

Skinny jeans are slim-fitting and hug the body from the waist to the ankle. They work for all different body types since they are often a stretchier jean.  

If you’re larger on the bottom like I am (size 12 and 5’6”, 160 pounds), the benefit of wearing skinny jeans is that you can wear an oversized top to balance out larger hips. And make your bottom look more proportional with your top. 

They’re ideal for petite women since they don’t overwhelm the frame by adding more bulk. 

And nothing plays up curves like skinny jeans. 

If skinny jeans work best for your body type, it’s more important to wear jeans that fit you well and that are flattering than to follow the newest jean trends. 

Many jean trends just aren’t very flattering. In case you need convincing, look at this dressing room picture of me in some very trendy but unflattering loose mom jeans. 

Loose jeans try on

See how wide and baggy the jeans are from the knee down? That doesn’t look good.

There’s a reason skinny jeans have been at the forefront of style for 10 years. The cut works for so many women.

To keep wearing them, combine your skinny jeans with other trending elements to look current.

In this post, I’m wearing an oversized white blouse with skinny jeans. This classic blouse is very trendy right now. To read about other current trends, check out my posts about collared sweaters, shackets and puffer vests.

Traditionally, you may think that knee-high boots are the best boots to wear with skinny jeans. And they are a classic look that works. But wearing ankle boots with skinny jeans is a great way to wear your skinny jeans in a fresh way. And to keep your look from going stale.

Ankle boots work great with so many different types of jeans. You can wear them with straight leg jeans or cropped flare jeans. And then with longer jeans like bootcuts and flares. 

In this post, I will show you how to wear skinny jeans with a variety of different ankle boots. 

First, let’s talk about the different ankle boots you can buy. 

Types of ankle boots

We tend to interchange the terms ankle booties with ankle boots. But ankle booties are a shorter boot than an ankle boot. They hit below or at the ankle.

When you’re picking out a pair of ankle boots, consider 4 things: shaft height, heel height, toe shape and color. 

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

There are 3 general shaft heights on your ankle boots. 

First up, low shaft ankle booties. They expose the ankle. The shaft is around 3-inches high. Since the ankle is exposed, they visually lengthen the leg line. And are perfect to wear with skinny jeans. Booties look most current when you wear them with a heel.

Second, we have a medium shaft ankle boot. This ankle boot hits a couple of inches above the ankle, measuring around 5 inches. To wear them with skinny jeans, you have to cuff or fold under the hem of the jeans. Don’t worry, I’ll tell you how.

Lastly, higher shaft ankle boots have a 6-inch shaft or more. They extend above the ankle by a few inches. You’ll need to cuff or fold under the hem of your skinny jeans with these boots too.

We’re seeing high shaft boots that lace up. Those are your Doc Martens. They resemble a pair of combat boots and have a high 6-½ inch shaft. 

And there’s also ankle-length western or cowboy boots. 

There are many different heel heights to consider. 

The ankle boot heel height you should buy is the heel height you’ll wear based on your height and lifestyle. 

While high heels make your legs look longer, if you’re going to be tortured by them, they’re not worth it. 

Toe shape is important too. Pointed-toe and almond shapes are elongating to your legs. 

The color of a boot also makes a difference. A boot that matches your skin tone visually extends your leg line. 

You can also match your jeans to your boots to make your legs appear longer. So wearing black boots with black skinny jeans visually lengthens your legs. 

Which ankle boots are right for you? 

To decide on the ankle boots that are right for you, you’ll consider your lifestyle. But you also have to wear what you love that feels like you. 

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 at 5’6”, I don’t own a single pair of them. 

The general guidelines I’m sharing here are a starting point. Take what tips resonate 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. 

Once you know the basic rules, then you can decide the ones that you’ll follow and dismiss. 

After all, good style also happens when you intentionally break the rules.

Now, ready to look at how to wear ankle boots with skinny jeans? Let’s dive in!

How to wear ankle boots with skinny jeans

You bring home a new pair of ankle boots and are excited to try them on. But when you go to put together outfits, nothing is working. I’ve been there!

Jean length and ankle boot shaft height make all the difference here. 

If you’re wearing skinny 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 your boot. So when you move, a sliver of skin shows. We’re trying to avoid having too much distance between the hem of your jeans and the top of the boot, which looks like you’re wearing high water pants. And also shortens the look of your legs. Go for less than 2 inches of skin showing. This length also shows off the boot.

If your skinny jeans come down below your ankle or you have a medium or high shaft boot, the easiest way to wear them is to cuff them or roll them under. When you’re done reading this post, hop over to Pinterest to watch my video on how to tuck under and cuff the hem of your skinny jeans. Follow me while you’re there so you never miss a video!

I’m here to be your style guide and show you all the different ways to wear them. Let’s look at all the ways to wear skinny jeans with various ankle boots.

A great way to style a pair of skinny jeans is with a low shaft bootie. So let’s look at that first. 

With a 3-inch low shaft ankle bootie

When you have an ankle-length skinny jean, the best option is to wear them with a low shaft bootie. 

An ankle-exposing bootie with a heel looks most current.

You’ll see me wearing these in a minute.

Booties may have a cut out on the side. If you feel comfortable showing your ankles, showing the ankle with a V-notch cut out lengthens the leg line. 

A flat bootie is a look we’ve been seeing for years that feels stale. Think about swapping these out for a heeled bootie.

That added height lengthens the leg line. Ideally, if you wear your skinny blue jeans with a longer shirt, you want to lengthen the leg line at the ankle. A longer shirt hides your waistline, which shortens the look of your legs. Don’t worry if you don’t want to show your ankles. I’ll show you how to make a higher shaft ankle boot work too.

Here, I’m wearing the above light taupe bootie with a V-notch ankle cut out on the side for maximum leg-lengthening. This has a low 3-inch shaft, with a 2.5-inch heel.

The beauty of wearing a low shaft bootie with a skinny jean is that the jeans hit above the top of the bootie. That means they don’t need to be rolled. Just put them on and go. 

Notice how the taupe color matches my skin tone. Matching shoes with your skin tone is a great way to make your legs look longer. 

What if you have a medium or high shaft boot in your closet? There are a few things you can do. 

Cuff the jeans once or twice creating the thinnest roll possible so you don’t cut the leg line and shorten the look of the legs. Or roll the jeans under.

With 4-inch shaft ankle boot

Below, I’m wearing a black chunky heel Chelsea boot with a 4-inch shaft and a 3-inch heel. 

Platform boots are in. And so are chunky lug sole Chelsea boots with an elasticized panel on the side. 

These heeled Chelsea boots are my favorite way to wear a lug sole Chelsea boot. They combine a platform with the casual side panel of the Chelsea for a super wearable shoe. Offering both height with comfort. 

In this look, I’ve cuffed the jeans just once creating a very thin cuff so that it doesn’t cut the leg line off. 

This is a more casual boot and a small cuff works well with it. 

And you can also cuff them under.

White blouse and platform Chelsea Boots and black chain purse

You could throw a black leather jacket over this outfit for an effortless cool look. 

If you’re wearing an oversized top or sweater with a skinny jean, these chunky black boots work because they balance out the proportions of the larger top. 

One thing to keep in mind is that the shaft height of your Chelsea boot will vary depending on the brand. 

Now, what if your shaft goes to 4.5 inches?

With a 4.5-inch shaft ankle boot

These ankle boots are a classic look with gray suede and a 4.5-inch shaft and a 2.5-inch heel and almond toe. 

The boot shaft is higher so the jeans need to be cuffed or folded under. Let’s look at both. 

Here they are cuffed twice.

Cuffing them can work here because the color of the cuff closely matches the color of the boot so the leg line doesn’t look radically shorter.

Here they are folded under.

Either look works. Decide based on your personal preference. If you’re going for a more casual look, cuff the jeans. If you’ll be more formal, roll the jeans under.  

Random aside, the other day I tried these boots on with a pair of cropped straight white jeans and they worked together perfectly. You can absolutely wear white jeans with ankle boots in the winter. 

Let’s keep going and take the boot shaft up to 5-inches. 

With a 5-inch shaft ankle boot

In the next group of pictures, I’m wearing Chelsea boots in brown with a flat sole. They have a 5-inch shaft and a 1-inch heel. This is a classic and timeless way to wear a flat ankle boot with skinny jeans.

Because the shaft is so high on these, the jeans need to be cuffed or folded under. Let’s look at both. 

Here they are rolled just one time.

This isn’t bad.

Here they are tucked under. I like this look even more.

Rolling the jean under creates a more polished look. That keeps a clean line at the ankle. And there’s no cuff to disrupt the leg line. 

You’ll see brown Chelsea boots and black Chelsea boots with a lug sole everywhere right now because they’re comfortable flat boots.  

With wider shaft boots 

If you have a pair of boots that have a wider shaft, like a duck or bean boot, you may not be sure what to do.

Here are two options.

To create space for the sock, you’ll need to fold the jeans under or cuff the jeans a few times. Then you’ll let the sock peek out. The best way to make your socks fit is to fold the top down and scrunch them down. 

It’s a good idea to match the color of the socks to the color of your jeans to keep a long line and a seamless look. 

Bean boots tucked under with navy sock

Here, I’m wearing the jeans folded under with a navy sock. This creates a very clean line.

Or choose a sock color that matches your sweater. In this pic, I’m wearing a camel oversized sweater and similar camel marled socks. And the jeans are cuffed a few times.

Bean boots cuffed with marled camel socks

Showing a sock creates a cute cold weather look you could wear to a fall festival or football game.  

Other issues

As I mentioned earlier, a higher shaft boot with a longer oversized top shortens the look of your legs. 

Now that you’ve seen all the looks, let’s compare the low shaft boot to the highest shaft boot so you can see what I’m talking about.

The low shaft bootie is the first image with the tan bootie. The higher shaft is the brown Chelsea boot in the second image. It’s 2 inches higher.

A lower shaft boot means you don’t need to cuff the jeans in a way that shortens the legs. The tan ankle bootie matches my skin tone, which also lengthens the leg line.

If you’re wearing a higher shaft boot like on the right, tucking the hem of the jean under is a good way to create a more seamless leg line so you lose less length visually. 

If you’re feeling stuck about what ankle boots to buy, here are some options to consider.


Read more about skinny jeans in my article Skinny Jeans vs Bootcut: How to Pick the Style for You.

How to wear ankle boots with skinny jeans

There are so many boot styles to choose from. You may think tall knee boots are the only boots that work with skinny jeans. But booties and ankle boots are just as versatile and stylish with them. 

Wear a low shaft bootie or a higher shaft ankle boot. Cuff the jeans once or twice or cuff the jean hem under. Wear them with a sock with a wider shaft boot. 

No matter what, choose the ankle boots you feel great in and that feel most like you. 

XO, Marya

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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