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Everything you need to know about how to wear ankle boots in 2022

Written by:

Updated:

Niki Whittle
October 31, 2016

Written by:

Updated:

Niki Whittle

October 31, 2016
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? 

You should NEVER pull your jeans over the top, 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.

And which ankle boots work with skinny jeans?

Lots! 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 17 years working as a personal stylist, helping women like you put outfits together that they love wearing, and this posts draws on that wealth of knowledge to share everything you need to know about how to wear ankle boots, so you can put together fall outfits that look good, with ease and confidence.

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.  

They come 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.  

They are a crucial component to fall outfits, that offer a wealth of options when it comes 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 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 height of boot is one that cuts you across a narrower part of your leg.


The reason being that the top of the 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 a square toe boot but worry that they will 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!

Likewise, if you like a pointy toe but don’t like how they make your legs look slimmer, choose a flat pointy toe boot with 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.

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 them so they sit above the boots, or choose a style of boots with a wider 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 or 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 dresses!  They often look a little more relaxed than a knee high boot, 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 skinny jeans

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

  • First off, choose an ankle boot with a wider ankle like this or this - this will enable you to tuck the jeans neatly inside the boot.
  • Look for ankle boots with a short boot shaft (a low cut bootie) 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 side 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.

outfit ideas for wearing ankle boots with skinny jeans

A women wearing ankle boots with skinny black jeans

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A wmen wearing a falloutfit with anle boots and skinny jeans

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A women wearing skinny jeans with ankle boots

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How to wear ankle boots with black skinny jeans

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How to wear ankle boots with black skinny jeans

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these are the best ankle boots to wear with skinny jeans in 2022

how to wear ankle boots with straight leg jeans

Straight leg jeans look great with 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 or this - this will allow the jeans to sit comfortably over the top of the ankle boots.
  • Many straight leg jeans are cropped so opting for a low rise pair of ankle boots like this 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,  ankle boots, cuff them to the right length.
  • Alternatively, you could crop them 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

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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an image of platfrom ankle boots worn with straight leg jeans

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an image of platfrom ankle boots worn with straight leg jeans

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an image of platfrom ankle boots worn with straight leg jeans

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these are the best ankle boots to wear with straight leg jeans in 2022

how to wear ankle boots with cropped jeans

Cropped jeans are the BEST style of jean to ear 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.  Your options are fairly unlimited, but with that said, I do think a narrower fitting, or short ankle boot will work the best.

  • A narrow fitting boot shaft will sit under your jeans easily
  • A tall ankle boot will avoid the annoying gap between boot and jeans
  • If you want to wear a wide ankle boot, choose a low rise boot to ensure that your jeans sit above them...otherwise they'll bunch on top of the booties
  • And if you're petite, or feel like cropped jeans shorten you, go for heeled ankle boots with a pointy toe to lengthen your legs.
an image of a women wearing ankle boots with cropped jeans

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 a cropped jeans. 

A women wearing cropped kick flare jeans with anke boots

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Image of a women wearing ankle boots with cropped jeans

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Image of a women wearing ankle boots with cropped jeans

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these are the best ankle boots to wear with cropped jeans in 2022

how to wear ankle boots with wide leg jeans

If your wide leg jeans are full length, the only factor you really need to consider is the heel height of your ankle boots, as any ankle width will fit under wide leg jeans.  I also recommend avoiding a round toe ankle boot as this can look dumpy and dated with a wide leg jeans.

If the wide leg jeans are cropped, you will want to choose an ankle boot that has a tall, tight ankle so they fit inside the jeans comfortably.

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

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

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these are the  best ankle boots to wear with wide leg jeans in 2022

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

Flares and boot-cut jeans look best worn with pointed toe ankle boots or platforms.   A round toe can look a little dumpy and dated with a flare.

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

a women wearing flares with ankle boots

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An image of a women wearing skinny flares with ankle boots

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these are the best ankle boots to wear with flares and boot-cut jeans in 2022

how to wear ankle boots with dresses

The main thing to consider when choosing an ankle boot to wear with a dress, is the length of your dress.   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 healed boot
  • A wider ankle also works, but watch where it cuts your leg, if it cuts across a wider part of your leg it will be less flattering
  • Pointy styles always look 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.

outfit ideas for wearing ankle boots with dresses

An image of a women earing ankle boots with a dress

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An image of a women earing ankle boots with a dress

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An image of a women earing ankle boots with a dress

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An image of a women earing ankle boots with a dress

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An image of a women earing ankle boots with a skirt

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A women wearing a pleated skirt with ankle boots

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An image of a women earing ankle boots with a skirt

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the best ankle boots to wear with dresses and skirts in 2022

conclusion

The truth is, that you will need a dew different styles of ankle boots in your toolkit.  One style is unlikely to work with everything in your closet, so take the time to understand what styles of ankle boots fit best with your collection, then go out and find them!

If you have any questions about how to wear ankle boots, get in touch - I'm here to help!

Disclosure: this post contains affiliate links, which means that if you purchase a product via these links I will earn a small commission. I NEVER link to products that I wouldn’t recommend to my clients, or purchase myself, in fact I own many of the styles linked here so can vouch for them! To find out more CLICK HERE