flat boots

19 Flattering Ways to Wear Flat Ankle Boots With Jeans

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

Hey friend! Flat ankle boots are some of the most comfortable boots to wear! If you’re on your feet running around all day long or you need to walk a long distance in your day. Or, if you struggle with foot pain, flat boots are a lifesaver. Or maybe flat boots just feel most like you. And now you’re wondering how to wear flat ankle boots with jeans. And how to create flattering outfits. It’s totally possible to create outfits you love with flat boots!

The ankle boots you need in your life, should be the boots you’ll actually wear and that feel like you and work for your lifestyle.

But without the height of a block heel, you may worry that your legs look very short.

I’m 5’6” tall and I love wearing flat boots with a heel of around an inch.

I’ll be your style guide and share with you styling tips for creating flattering and stylish outfits with flat ankle boots and jeans. And just for fun, I’ll also show you some dress and skirt outfit ideas using flat ankle boots.

But first, let’s talk about types of ankle boots. Understanding the different types will make it easier to create outfits you love.

Types of ankle boots

We use the terms ankle booties and ankle boots interchangeably. But ankle booties are shorter than an ankle boot. They hit below the ankle or right at the ankle and may have a cutout on the side of the bootie. 

Ankle boots hit above the ankle and may extend several inches above the ankle. The part of the boot that goes up your ankle is called the shaft. It goes from the top of the heel to the top of the boot.

Low shaft ankle booties have a shaft around 3-inches high. And the ankle may be exposed.

Medium or mid-height ankle boots hit about 2 inches above the ankle, coming in around 5 inches total. Higher shaft ankle boots have a 6-inch shaft or more. They go above the ankle by a few inches. 

Chelsea boots are a good example of a flat, medium to high shaft boot. Their shaft height varies depending on the brand you buy. 

When you consider ankle boots, toe shape is important too. Pointed toe and almond shapes elongate your legs.  

The color of your ankle boot makes a difference too. A boot that matches your skin tone makes your legs look longer. As does matching your jeans to your ankle boots. So wearing black boots with black jeans is a great way to stretch the leg line. 

When you’re wearing low ankle boots, there are many different ways to keep your leg line looking long and flattering. 

If you’re struggling to create outfits you like, keep reading, I’ve got some ideas for you.

Let’s take a look!

How to wear flat ankle boots with jeans in 2022

Wear flat boots with high-rise jeans 

Wearing high rise or extra high-rise jeans and exposing the waistband helps to lengthen the look of your legs.

The rise of a jean is the distance from the top of the front waistband down to the crotch seam. High rise or high-waisted jeans tend to hit at or above your belly button. This is at your natural waist or the part of your waist that bends when you lean to the side. High rise jeans may measure anywhere from 9 to 10 and even 10 and a half inches.

Extra high rise jeans may go up to 12 inches or 12.5 inches. 

To choose the right rise for your body type, read my post about choosing the right rise for you.

Wearing a high-rise jean with your flat boots is a great way to lengthen the leg line. 

Let’s take a look at me wearing a pair of high-rise skinny jeans and medium-rise skinny jeans with flat boots so you can see the difference in the leg line. 

I’m wearing them both with my flat brown ankle boots. These Chelsea boots have an elastic panel on the side that gives it a classic look. They are the best ankle boots if you want a timeless rather than trendy look. 

First up, let’s look at them with high-rise skinny jeans. 

high-rise skinny jeans outfit

Notice how I’ve half-tucked the shirt to expose the waistline. I also tucked under the hem of the jeans so a cuff doesn’t shorten the leg line at the ankle. 

In the next photo, I’m wearing mid-rise skinny jeans. I front-tucked the shirt to expose the waist. 

mid-rise skinny jeans outfit

The legs also look shorter because I cuffed the jeans. And the cuff visually cuts off the legs. They would look a bit longer if I’d folded under the hem of the jeans instead. 

Now take a look at these two photos side by side. See how my legs look longer in the first image with the high-rise jeans? 

I’ve devoted an entire post to how to wear skinny jeans with ankle boots, including how to tuck under the hem, so definitely check that out if you have more questions.

Let’s look at the next strategy, which is to wear your flat boots with long jeans. 

Wear flat boots with long jeans like bootcut jeans, flare jeans, or straight leg jeans

You may wonder if you can wear flat ankle boots with long jeans like bootcuts, flares and longer straight leg jeans. 

The answer is, of course, yes! This can be very flattering! Let’s take a look and see. 

With bootcut jeans

Bootcut jeans are a great option and they’re coming back in style. These are high rise and slim fitting on the top half. And wider from the knee to the ankle. 

high-rise bootcut jeans outfit

If you’re like me and you have wider hips and a rounder bottom, with a smaller chest and shoulders, this body shape naturally makes your legs look shorter. The bootcut balances out the proportions of wider hips. And since they have a longer length, legs look longer in them too.

In this outfit, I’m wearing a relaxed fit sweater. And a belt so the waist is highlighted. The belt also pulls in the color of the boots in a second spot. I’ve front-tucked the sweater and pushed up my sleeves to emphasize my waist. And to keep the top from looking frumpy.

In the next picture, I’m leaving this short chunky sweater untucked and my legs still look nice and long. 

high-rise bootcut jeans outfit

Let’s look at some flare jeans outfits next.

With flare jeans

I’m so happy flare jeans are back in style! There’s something that feels super empowering about wearing them. 

Flares have a wider bell from the knee down than bootcut jeans. And they’re also longer. Ideally, the hem of the jean hits the top of the toe box and breaks an inch or 2 above the ground.

These flare jeans are high waisted and they’re in a size 12 short length. I bought them specifically to wear with flat shoes. 

high rise black flare jeans outfit

You’ll see black and brown being worn together right now for a very chic look. 

Here, I’m wearing a relaxed and chunky knit crewneck. I’ve front tucked the sweater, pushed up the sleeves, and am wearing a belt to highlight the waistline.

In the next picture, I’m wearing a fitted gray sweater that’s front-tucked, again, to highlight my waistline. 

high-rise black flare jeans outfit

Now, let’s look at some straight leg jeans that are more tapered at the ankle. 

With straight ankle length jeans

True straight leg jeans are as wide at the ankle as they are at the knee. If you have a true straight leg jean, when you fold the hem up to the knee, the knee and the hem are the exact same width. 

But you’ll see that stores are also offering straight jeans that are tapered at the ankle. They’re not as tight as skinny jeans but still slim fitting in the ankles. 

That’s what I’m wearing in the next picture. Tapered straight jeans may be cropped or come to the ankle. This pair stops above my ankle line.  

straight jeans outfit

I’ve paired these jeans with a simple white top.

Wearing a boot that matches the color of your jeans also creates a very flattering silhouette. 

Wear a boot that matches the color of your jeans

Another easy way to lengthen the leg line is to wear a boot that matches the color of your jeans. Pair black boots with black jeans for a long line. 

Here, I’m wearing a pair of medium ankle boots. The heel is just over an inch.

black flares with black ankle boots

Combining these black flare jeans with black ankle boots creates one long block of black.

Notice I left the sweater untucked, but pushed my sleeves up. With the sleeve pushed up, the waistline feels more defined. 

Another flattering strategy is to wear a boot that matches your skin tone. 

Wear an ankle boot that matches your skin tone

Here’s another great option for lengthening your leg line. And that’s wearing an ankle boot that matches your skin tone. 

In this picture, I’m wearing skinny jeans with a taupe ankle bootie.

tan ankle booties with skinny jeans

A skin-tone colored shoe is one of the most versatile shoes you can buy. This pair of boots stops right below the ankle line, which allows the skinny jeans to fall straight and stop at the top of the ankle boots, creating a long clean leg line.

Let’s look at a final strategy to lengthen the leg line and wear a flat boot with jeans. And that’s wearing a pointed toe boot.

Wear a pointed toe boot

Pointed toe boots are celebrated for their ability to lengthen the leg line. But, my friend, I haven’t found a pair of pointed toe ankle boots that feel like me, so I don’t own any. I’ve returned a lot of pairs. All that to say, if style advice doesn’t feel like you, find another style that works and feels good to you.

These brown boots are my version of a pointed toe boot. 

A rounded toe with a long lean toe box is the next best option. It has the same visual effect of lengthening the leg line. And they’re more comfortable too!

Here I’m wearing them with a pair of tapered straight leg jeans.

In case you love cropped straight jeans like I do, let’s talk for a sec about how to wear flat ankle boots with cropped straight-leg jeans.

How do you wear flat ankle boots with cropped straight leg jeans?

At 5’6”, I buy my straight-leg jeans in ankle-grazing lengths. I like the Audrey Hepburn 1950s cropped pants look. And, even though I love bootcut jeans and flare jeans for how long they make my legs look, cropped pants express my personal sense of style. You have to honor your personal preferences when you’re getting dressed. That’s what creates your personal sense of style!

True straight jeans that are cropped can be worn with low booties and a higher shaft pair of ankle boots. Let’s look at both.

Here, I’m wearing ankle booties that match my skin tone and have an ankle cut out. 

straight cropped jeans with tan ankle booties

The taupe color and showing the ankle lengthens the leg line. You want to show some skin, but not so much that it looks like you’re wearing high water pants. Showing 2 inches or less of skin is a good amount to avoid that look. 

With a higher shaft boot, the best way to wear them is so the hem of the cropped straight jeans hit right at the top of the boot.

In this picture, my flat brown boots have a 5-inch shaft. And the cropped straight jeans hit perfectly right at the top of the boot, revealing just a sliver of skin. 

straight cropped jeans outfit

Here they are with my cropped black jeans, and they hit perfectly in the same spot.

black cropped jeans outfit

If your jeans come down over the top of your ankle boot, that works too, just like we saw above with the tapered straight jean. In my opinion, that’s the easiest way to wear straight jeans. 

This look shows off the ankle of the boot.

You can see that look in this picture. 

cropped jeans  outfit

Here are some cropped black jeans with black ankle boots.

Again, wearing black jeans with black ankle boots creates a column of black and extends the leg line visually.

Here’s one more look with cropped black jeans, flat black Chelsea rain boots and a gray sweatshirt.

Now, you may wonder if you can wear your flat ankle boots with skirts and dresses.

Are flat ankle boots okay to wear with a skirt or dress? 

Absolutely! It’s a modern way to wear your skirt and dress outfits. 

Let’s look at an outfit with a straight skirt. This skirt hits a couple inches above the knee. 

With a straight skirt

straight skirt outfit

This is as short a skirt as I feel comfortable wearing. 

With a short skirt, opt for a pair of tall boots, especially if you’re going into a professional or more formal setting. A medium-high shaft ankle boot like this can also work. This brown flat Chelsea boot has a 5-inch shaft that’s perfect with this. Be careful with a shaft that comes up too much higher because it will cut the leg line at the wider part of the calf and create a shortening effect. 

When you’re wearing a skirt with an ankle boot, make sure the shaft fits tighter around the ankle. A loose ankle boot makes legs look like toothpicks or frumpy. 

If you’re wearing a pencil skirt that comes down below the knee, go for a lower shaft bootie so the leg line looks longer, and preferably choose one that’s flesh toned. 

I’d add a matching brown bag to this outfit to tie the boot color into a second spot so it looks intentional.

Let’s look at a longer black skirt outfit. 

With this black midi skirt, I’m wearing black ankle boots that have a medium-high shaft that’s fitted to the ankle. Midi skirts are about as long as I go since I always feel swallowed up by the fabric of a maxi skirt at 5’6”.

long black skirt outfit

Paired with a black skirt, these black boots create one long lean line. You can add some black tights or black leggings to stay warm. Or, to look more casual, wear a black leather jacket over the outfit.

Alright, let’s look at a dress!

Next up is a navy floral dress with a dark jean jacket.

dress outfit

I wore this outfit wine tasting. Certainly you can wear a tall boot with a short dress, but wearing an ankle boot creates such a fun, casual look!

The brown of the boot looks beautiful with navy and dark denim and picks up the orange tones in the floral print.

You can wear this going from winter to spring. And from summer to fall. 

How do you wear flat ankle boots?

To create super flattering outfits with jeans and flat ankle boots, extend the look of your leg line as much as possible. There are 5 ways to do that. Choose high-rise jeans. Wear full-length jeans. Match the color of your boots to your jeans. Wear flesh-toned boots. And finally, choose pointed toe ankle boots. 

Experiment with different looks. Take selfies in the mirror and then look at the pictures to get an objective sense of what looks best. 

Wearing ankle boots with jeans, skirts and dresses creates a fun, and modern silhouette. You’ve got this!

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.

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.