how to style ankle boots

How to wear ankle boots 9 ways

Ankle boots are my most worn boots in the fall and winter. And honestly, even in the spring. They go with jeans, dresses, skirts (mini and maxi dresses) and will help elevate any look where you just threw on sneakers. They are super versatile in that you can wear them with casual looks like jeans and t-shirts, but they can also be dressed up enough to pair with an office or date night dress. But I think one of my favorite things about ankle boots is that they help transition pieces from summer to fall or winter to spring.

How to wear ankle boots

When thinking about how to wear ankle boots, there are a few things to keep in mind. There are so many different styles of shoes and not every shoe goes with every outfit. Some ankle boots have a high or low ankle. There are those that are tighter around the ankle and those that are wider. Each one goes well with other items in your wardrobe and may look better with certain pieces than others.

I have several different types of ankle boots in my closet that go with different things. I have these taller boots and tighter ankle boots to go with the dress and skirt. Or they’re good with leggings because they’re fitted and the shoe sits nicely over them. Then there are these lower chelsea boots that go best with my jeans that allow a little ankle to show. It also goes well with dresses and skirts.


I have yet to really find one ankle boot that goes with everything. With so many different styles and only some working with certain bottoms, I think you need to have a few styles in your wardrobe. I don’t think you need a TON. But definitely enough to match the types of outfits you own and wear the most.

Flat ankle boots are great for everyday wear, comfortable and stylish. It goes with most of your items from jeans to dresses. But because they are flat, you may not feel like they are dressy enough for the office.

A fun trend for this weather is to wear a peep toe or open toe ankle boot. These laser cut peep toe boots are super fun for spring and fall.

There are also low booties, the ones with side cutouts like the ones shown above. There are high ankle boots that hit more mid-calf as opposed to those that can hit right at the ankle. For winter, there are winter ankle boots that are warm and cozy. And then my personal favorite, thanks to ALL the rain, are these waterproof ankle boots.

And there are also SO MANY different styles from western inspired, to pointed toe boots, to go-go inspired white boots. The options are really endless, and ankle boots can be found for every outfit, every style and every price.

Tips for styling ankle boots


When you are petite or have short legs, it is important to always keep leg lengthening in mind. This usually means adding a heeled bootie, a pointed toe, or at least a rounded toe. It probably also means you should avoid mid-cut ankle boots. It can really cut you off if not done right. The only time a mid-body ankle boot could potentially work is if you’re going monochromatic. So all black, or black with dark dark jeans and so on. It will help you build a longer streak and work in your favor.


For someone like me who lives in my jeans, I’ve come up with every possible combination of ankle boots and jeans in my wardrobe. There are certain jeans in my wardrobe that go well with certain shoes. Then there are those that require really low ankle boots that go well with jeans that have a longer inseam. And then there are these Everlane jeans that I love, they’re basically short inseams for almost a petite figure that work with all my taller shoes.

It seems silly that just a few inches in a shoe or a pair of jeans will make a big difference, but it does. When your jeans start to form in your boots, it can look disheveled and disheveled. So keeping the lines clean, good tailoring and the right shoe will create a more flattering look overall.


If you live in an extremely cold climate, you’ll probably want to go for an ankle boot that covers your ankle with a higher shaft. This way you stay pleasantly warm! You can also add interest to your look by letting a bit of your socks show.


how to style ankle boots
how to style ankle boots


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how to style knee high boots

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