11 Best Tips on How to Wear Leather Ankle Boots

Ankle boots are something that you can wear year round. In this blog post, I am going to specifically talk about the popular leather ankle boots. Styling them can be both easy and hard. It is easy because they almost always look good with skinny jeans; it is hard because things can get a little tricky when you are not wearing jeans. I am about to show you a list of some of the best leather ankle boots outfit ideas that I have put together. Let’s check them out.

Black Leather Ankle Boots with Sleeveless Cropped Tee

black leather ankle boots sleeveless cropped t shirt

As mentioned at the beginning, leather ankle boots are something that you can wear year round. I agree that they are better suited for the cold weather but they do also look just fine for the summer if you enjoy looking more unique. So, as a little of surprise, I am going to start off the list with a summer outfit to prove the point. For this outfit, you can wear a black sleeveless cropped print tee for the top and pair it with black cropped jeans and the leather ankle boots.

Wear with Sleeveless High Neck Top & Black Skinny Jeans


Here is another summer outfit before I move on to talk about the fall and winter outfit ideas. Simply wear a form fitting, sleeveless, high neck top with black ripped skinny jeans and matte leather ankle boots.

Wear with Black Leather Jacket & Skinny Jeans

black ankle boots leather jacket outfit

Leather jacket and leather ankle boots are a perfect match, period. Not only because that they have the same texture and the same color, it is the combination of the usually form fitting cutting of leather jackets and the way ankle boots only covers up to a few inches above the ankle that makes the entire outfit tight and fit, making you look tall and slim. As a perfect demonstration, this outfit consists of a white top, a black leather jacket, black skinny jeans and leather ankle boots. This is such a cool and smart looking outfit that you can both wear to work or wear casually.

Wear with Leather Pants & Long Wool Coat

leather pants black ankle boots wool coat

Here is an outfit idea that explores the possibility of putting together leather leggings and leather ankle boots. To complete the outfit, pair the mentioned pieces with a grey knit sweater and a light grey long wool coat. The result is an outfit that looks both elegant and cool.

Brown Leather Ankle Boots with Comfy Sweater & Jeans

brown leather ankle boot sweater boyfriend jeans

One of the best ways to style the brown leather ankle boots is to wear it with washed denim jeans. You can keep it simple by wearing a black comfy knit sweater for the top. This is a minimal outfit that is so comfortably looking. It is an ideal casual outfit for the fall and the spring.

Brown Ankle Boots with Black Dress & Wool Cardigan

brown ankle boots black t shirt dress leggings

Brown leather ankle boots are as beautiful as the black ones. Let’s have another outfit idea that involves the brown boots. For the top, you can wear a black t shirt dress or shift dress. Wear a grey wool cardigan over the dress. Complete this feminine outfit is black leggings and brown ankle boots.

Wear with Oversized Knit Sweater & Wool Coat

black ankle boots comfy sweater wool coat

This outfit is a perfect example of how to dress beautifully with oversized sweater. When it comes to wearing oversized clothes, the proportion is the key, as you can look short or clunky if you mess that up. To achieve a well balanced proportion, for the top, you should wear a high neck oversized knit sweater and layer over it another oversized item in the brown wool coat. To balance out the loose top, you need something not only form fitting, but also extend the length of your legs visually for the bottom. To do that, you can wear cropped black skinny pants with black leather ankle boots. Don’t underestimate the two inches of skin that shows between the cropped pants and the boots. They are there to make your legs look long.

Wear with Cream Dress & Green Wool Coat

cream dress army green coat black boots

I put this outfit idea here on the list simply to show an interesting and good looking color combination. The outfit consists of a cream dress, a forest green wool coat, black leggings and ankle boots. For those of you that like the color of forest green, you may be interested in our blog post on how to wear forest green.

Grey Hoodie & Black Leather Jacket

black ankle boots grey hoodie black leather jacket

As a fan of hoodies, I always try to explore different ways to integrate into outfits of different styles. When you put a hoodie together with a dark and cool outfit, it very interestingly make the outfit looks much more causal and creates a softer tone. This outfit is a good example. Pair a typical grey hoodie with a black leather jacket, black skinny jeans and ankle boots to achieve this casual yet cool look.

Black and White Vertical Striped Shirt & Brown Leather Jacket

black and white vertical striped shirt leather ankle boots

For outfits that involve the leather jacket and the ankle boots, you can put them together with a button up shirt too. For example, wear a black and white vertical striped shirt with a brown leather jacket, black skinny jeans and ankle boots.

Black and White Striped Shift Dress & Black Leather Jacket

black and white striped shift dress leather ankle boots

Having mentioned quite a lot of outfit ideas that use skinny jeans to pair with black leather jackets, let’s talk about one that uses a dress. You can simply wear a black and white striped shift dress under your leather jacket. Wear black leather ankle boots with no leggings. For this particular jacket, it has a little bit of twist, which is the faux fur collar and that adds a touch of elegance to the entire outfit.

There are some of my favorite ways to style the leather ankle boots. I am sure that there are many fans of boots who are always exploring how to style different boots, such as suede boots, knee high boots and thigh high boots. If you are one of those fans, please navigate around our website. We have have together hundreds of boots outfit ideas that we want to share with you.