Everything you need to know about how to wear ankle boots in 2024

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Updated:

January 30, 2024
How to wear ankle boots

Ankle boots are everywhere, in every conceivable style, yet they are one of the hardest pieces of footwear to style! So much so that one of the most common questions I get asked in the fall season is: How do I wear ankle boots? Along with…

Should I tuck my jeans into the ankle boots, or pull them over the top? 

Don't stretch your jeans over the top of your ankle boots, it looks dated and uncomfortable, you should do this instead.

Can I wear ankle boots with dresses? 

Yes! The right ankle boots look amazing with dresses.  Here are some great options.

Can I wear ankle booties with dresses?  

Yes! The right ankle boots look amazing with dresses.  Here are some great options.

And which ankle boots work with skinny jeans?

My favorites are short western-style ankle boots, and barrel boots, but there are lots more! See here.

If you’ve asked yourself the same questions, you’ve come to the right corner of the internet! I've spent the last 18 years working as a personal stylist, helping women like you put outfits together that they love wearing, and this post draws on that wealth of knowledge to share everything you need to know about how to wear ankle boots in the winter months, so you can put outfits together for the colder months that look good, with ease and confidence.

Short on time?

these are the top 3 ankle boot styles for 2023

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best ankle boots wearing with for mom jeans

a pair of mom jeans worn with ankle boots

watercolor ankle boot

This is a PERFECT ankle boots for wearing with mom jeans.  The ankle is narrow so it will sit inside the hem of the jeans. and the heel is low so they align with that relaxed look.

best ankle boots for straight-leg jeans

black straight-leg jeans worn with ankle boots

the chelsea boot

This style looks great with a straight leg jean and the shape is perfect - the fitted ankle sits neatly inside the hem of a straight leg, and the tall shaft fills the gap when the jeans are cropped.

best ankle boots for wide-leg jeans

a pair of dark blow wide leg jeans worn with western style ankle boots

mandey boots

A western style ankle boot always looks great with a wide-leg jean - long or cropped. 

what are ankle boots?

Ankle boots (also known as booties) are boots that have a short boot shaft that sits at the ankle or just above.

There are lots of different types of ankle boots, in a range of shaft heights from a low ½ inch right up to tall 5 inches. They come in all toe shapes, from pointy to square and almond to round, and they come in all heel heights - from block to stiletto.

They are a crucial component to fall outfits, that offer a wealth of options when it comes to putting different looks together, yet they are one of the hardest items of footwear to style.

how to find the right ankle boots for your body-shape

It’s a fact that some ankle boots will look better on you than others, but if you don't know which boots work best for your body-shape and why, you’ll end up wasting money on booties that don’t look good or that you can’t figure out how to wear, or what to put them with.

So, before you dive into how to wear ankle boots, and which ankle boots go with what - I recommend taking some time to learn which styles will work best for YOU. 

Trust me, once you have this information it will be so much easier to shop for ankle boots (because you’ll know what to avoid), and it will be so much easier to put together outfits that look as good on you as they do in your head!

To find the best ankle boots for you, take these 5 points into consideration:


1

CONSIDER THE BOOT SHAFT HEIGHT FOR YOU

The point at which the top of the ankle boot hits your leg will affect how flattering they are.

The general rule is that the most flattering shaft height of the boot is one that cuts you across a narrower part of your leg.

The reason is that the top of your boot will draw a line across your leg, so if it does this at a narrow point, your legs will look slim; and if it draws a line around a wider point, your legs will look wider. So, choose a pair that highlights the point you want to show off!

2

THINK ABOUT THE HEEL SHAPE

If you carry your weight on your bottom half, or have a bottom heavy shape like a pear shape, then you might find that a slim, kitten or stiletto heel looks a little squashed on you.  If that's the case, try a chunky, block heel instead.  It will be much more flattering.  

On the other hand, if you have very slim legs then a chunky heel can emphasize slimness and  look a little clumpy.  You'll find that a slim, kitten or stiletto heel will balance your frame much better.

3

think about the width of the ankle boot shaft

A neat fitting ankle boot with a narrow ankle like this will slim and elongating your legs.  However, try to avoid choosing an ankle boot that is very tight as this can have the opposite effect and can make legs look chunkier than they are.


A wide ankle can also make legs appear slimmer, however, if you have slim legs, an ankle boot that gapes at the ankle may look clump on you and make your legs look slimmer than they are.

4

consider the ankle boot's toe shape

A pointed toe will elongate the leg, making it appear longer and narrower, whereas a square or round toe may shorten your leg.

5

play around with different combinations to find the best option for you

If you like square-toe boots but worry that they make you look dumpy, you can mitigate this by choosing a square-toe ankle boot that has a high heel and a tall boot shaft! This will elongate your leg and prevent you from looking squat.

Likewise, if you like pointy-toe booties but don’t like how they make your legs look slimmer, choose flat ankle boots with a pointed toe and a lower boot shaft.

Once you understand which elements work best for your legs and your frame, you can be more choosy and ultimately find the ankle boots that work best for you.

want to know more about which clothes work for your shape?

My simple guide will show you exactly what the most and least flattering clothes are for your shape, so you can start creating outfits that look good on you ?

should you tuck your jeans into your ankle boots?

The only time you should tuck your jeans into your boots is if they fit neatly inside the ankle with no ruching or bulk.  If you need to wrap your jeans around your ankle to fit them in the booties, don't do it.

Skinny jeans are typically the best style for tucking into ankle boots, but if the boots have a wide boot shaft, or are a looser fit like this  or this , you may be able to tuck a straighter leg jean into them.  But typically, the hem of your jeans needs to be super tight at your ankle, to fit them neatly inside an ankle boot.

If your jeans don’t fit inside neatly, or they bulge out the top of the boots when you tuck them in, you have 2 options:

  1. Cuff your jeans so they’re just sitting above the top of the boots. You can do a small cuff or a wide cuff, it can be neat or messy, whichever you prefer...or whichever is needed to get the length just right.
  2. Or, (this one may seem a little more drastic) you could chop off the bottom of your jeans and leave a raw edge like this that sits just above the top of the boots. I've done this to a couple of my skinny jeans and I love the look.

is it OK to stretch my jeans over the top of my ankle boots?

I always think this looks a little odd and somewhat dated, especially if the jeans are so tight that you can see the silhouette of the booties through them then. 

You'll also probably find the jeans ride up over the top of the boots, which will be super annoying, not to mention uncomfortable.

Instead, I suggest cuffing the hem of your jeans so they sit above the boots. Or choose a pair of boots with a wider, looser ankle so the jeans can be tucked inside them. There are some ideas below for cuffing your jeans.

how to cuff your jeans with ankle boots

There are a few different ways to cuff jeans, and I recommend playing around and experimenting with what works best for you and your outfit.

  • If you have lots of fabric that needs shortening, try a messy cuff.  The way I do this is to do one large cuff, and then a second cuff on top of that - don't worry about lining everything up neatly, it’s supposed to look messy…like you just pushed the hem up.
  • A rolled cuff is a good option if you like a neat looking cuff.  Just cuff, and cuff again to hide the hem of the jeans
  • If there isn't much fabric to shorten, just do a simple narrow, one cuff.  
  • And lastly, another good cuff to do if you have long jeans to turn up, is to make a feature of the cuff and go large.  This works particularly well with dark blue jeans.
images of different ways to cuff jeans with ankle boots

what to do about the gap between the hem of your pants and the top of your booties

If it’s not too cold I suggest simply leaving the gap bare, especially if you're wearing white ankle boots.  Otherwise I suggest wearing skin colored tights or socks, or maybe even fishnets.  I always think this is the best look.

If it’s too cold to bare any flesh you have a couple of options:

  • You can make a feature of the gap and wear colored socks or tights, or patterned socks or tights - I love metallic or leopard.
  • Or, you can wear socks or tights in the same color as the ankle boots - this is a great way to create a column that elongates the legs, so if you're petite you might want to try this.

Whichever option you go for, think about the weight and thickness of the socks and make sure that they compliment the boot style.  For example, if you’re wearing a tight fitting sock boot a fine knitted sock or hosiery will be a better fit than a chunky cable sock.

is it ok to wear ankle boots with a dress?

Absolutely! Ankle boots look great with all dresses, especially a long dress of maxi dress! I often think an ankle boot looks a little more relaxed than a knee-high boot with a dress, and they give you lots more options for styling, too.

You just need to choose the right style for the length of your dress.  I’ve shared lots of great options to wear with dresses here, and there are a couple of outfit ideas to inspire you here.

a photo of a women whowing you how to wear ankle boots with a skirt

how to wear ankle boots with different clothing styles👇

1

how to wear ankle boots with skinny jeans

Skinny jeans can be tricky to wear with ankle boots, particularly if there isn't enough space inside the bootie to tuck your jeans in.  So here are some tips on wearing ankle boots with a pair of skinny jeans:

  • Choose a western-style ankle boot with a wide ankle like this or this - this will enable you to tuck the jeans neatly inside the boot.
  • Opt for a pair of combat boots that have laces that can be worn loose enough to tuck a pair of skinny jeans inside
  • Look for ankle boots with a short boot shaft like this, or a low-cut bootie like this so that your jeans sit comfortably above the top of the boot.
  • If your jeans are too long to sit above the ankle boot, or too bulky to sit inside the ankle boots, cuff them to the right length. For some ideas on how to cuff your jeans, head here.
  • Or, if you're up for some simple DIY, consider cutting turning your skinny jeans into split -hem jeans but cutting a short slit in the side of  each hem so they sit over the ankle boot.  Or cut the hem and leave a raw edge that's the correct length.

top 3 ankle boots to wear with skinny jeans in 2023

Western style ankle boots

lug sole ankle boots with a wide ankle

Pointed toe stiletto ankle boots

outfit ideas for wearing ankle boots with skinny jeans

A women wearing ankle boots with skinny black jeans

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How to wear ankle boots with black skinny jeans

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the 20 best ankle boots to wear with skinny jeans in 2023

2

how to wear ankle boots with straight leg jeans

Straight-leg jeans look great with a pair of ankle boots, but they do have a tendency to bunch up on top of ankle boots...unless you choose the right style.

Here are some tips to help you choose the right ankle boots to wear with straight-leg jeans:

  • Go for an ankle boot with a narrow-fitting ankle like this lug sole bootie or a stretch boot like this which will allow the jeans to sit comfortably over the top of the ankle boots.
  • Many straight-leg jeans are cropped so opting for a short pair of ankle boots like these hiking-style boots will work well.
  • If your jeans are too long to sit above the ankle boots and too narrow to sit over the top of them, cuff your jeans to the right length.
  • Alternatively, you could cut your jeans to the right length to sit above the ankle boots. Or, cut a slit into the hem and turn them into split-hem jeans so they sit over the top of the boots.

top 3 ankle boots to wear with straight leg jeans in 2023

Pointed toe sock boots

Square toe heeled booties

Western style ankle boots

outfit ideas for wearing ankle boots with straight leg jeans

an image of platfrom ankle boots worn with straight leg jeans

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the best ankle boots to wear with straight leg jeans in 2023

3

how to wear ankle boots with cropped jeans

Cropped jeans are the BEST style of jeans to wear with ankle boots. You don't have to decide whether or not to tuck the jeans inside the boots because they sit above the ankle boots - perfect!

Your options are fairly unlimited when it comes to ankle boot styles, but with that said, I do think a narrower fitting or short ankle boot will work the best.

an image of a women wearing ankle boots with cropped jeans

top 3 ankle boots to wear with cropped jeans in 2023

Lug sole Chelsea boots

Heeled, western ankle boots

Pointed toe sock boots

outfit ideas for wearing ankle boots with cropped jeans

Cropped jeans or pants can make you look shorter and wider than you are, so a great way to mitigate this is to team them with a sock boot. Sock boots are tight around the ankle and sit neatly inside the leg of cropped jeans.

A women wearing cropped kick flare jeans with anke boots

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the 20 best ankle boots to wear with cropped jeans in 2023

4

how to wear ankle boots with wide leg jeans

In the summer, wide leg jeans are easy - you just throw on a pair of Birkinstocks or Teva's and you're good to go.

In the cooler months it's a little trickier.  Shoes or sneakers work well, but they're not super warm in the depths of winter, so if you want to keep wearing your wide-leg jeans throughout 2023, here are some tips:

If your wide-leg jeans are full-length, the only factors you really need to consider is the heel height of your ankle boots, and the toe shape, as any ankle width will fit under wide-leg jeans.   I like a chunky sole, a pointy toe, or a squared toe ankle boot.  I'm currently loving pairing wide leg jeans with chunky ankle boots that have a monk strap like this, or that have loafer detailing like this pair of ankle boots.  And I recommend avoiding a round-toe ankle boot as this can look dumpy and dated with a wide-leg pant.

If the wide-leg jeans are cropped, you will also want to choose an ankle boot that has a tall, tight ankle (like this sock boot, or this pair of tall lug sole boots) so they fit comfortably inside the hem of the jeans.

top 3 ankle boots to wear with wide-leg jeans in 2023

pointed toe ankle-boots

Square toe sock boots

Western-style ankle boots

outfit ideas for wearing ankle boots with wide leg jeans

an image of a women wearing ankle boots with cropped wide leg jeans

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5

how to wear ankle boots with flares and boot-cut jeans

Flares and boot-cut jeans look best worn with western-inspired boots, pointed-toe ankle boots, square-toe ankle boots, or platform booties. A round toe can look a little dumpy and dated with a flare.

top ankle boot styles to wear with flares in 2023

Western-style ankle boots

Pointed toe ankle boots

Black flare jeans worn with wooden platform ankkle boots

Platform ankle boots

outfit ideas for wearing ankle boots with flares and boot cut jeans

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6

6

how to wear ankle boots with dresses and skirts

The main thing to consider when choosing an ankle boot to wear with a dress is the length of your skirt. If the dress is a midi or mini you'll want to watch where the top of the ankle boot hits your leg and aim for a height that highlights a flattering part of your leg.

In general, my tips for matching ankle boots with dresses or skirts are:

  • A tight ankle will be the most streamlined and so will be the most flattering. It will elongate and slim your leg, especially if it's a heeled boot
  • A wider ankle also works if you're going for a casual look, but watch where it cuts your leg, if it cuts across a wider part of your leg it will be less flattering
  • Pointy styles are a classic look that always looks great as they elongate and slim the legs
  • And lace-up styles are a great option as they offer you the ability to wear the boot as tight or loose as you like.

The top ankle boot styles to wear with dress and skirts in 2023

Short cowboy boots