Everything you need to know about how to wear ankle boots in 2023

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.

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:

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.
   

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.

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 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.

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.

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: