The Best Shoes to Wear With Ankle Pants
top of page
  • Writer's pictureBrenda

The Best Shoes to Wear With Ankle Pants

Updated: Oct 15

Ankle pants are considered at least an office wardrobe staple, if not a general wardrobe staple, thanks to their more professional look and ease of wear. They come in different lengths and cuts as well as varying amounts of flair, but one thing is certain; they can be worn across different seasons.

With winter right around the corner, you may be thinking it’s time to pack up your cropped pants and jeans but I’m here to tell you that won’t be necessary.

In this post, I would be showing you different ways to style a pair of ankle pants for not just the warmer months but also the winter seasons. If you are looking for what shoes to wear with ankle pants during the winter, then you want to keep reading.


Let’s start by answering the question below:

What are ankle pants?

Ankle pants refer to pants that hem at the ankle. They are typically shorter than regular pants and hit right at the ankle bone. What is great about them is that they can be styled with so many types of shoes thanks to their shorter length and don’t require much effort. They can be styled up or down as well to create more business-appropriate looks or casual looks, if paired with the right shoes.

In today’s blog post, I would be showing you different ways to style a cropped pant, taking into account the different seasons as well as the different dress codes you may be dressing for. This post is meant to serve as a guide to show you the different shoes you could pair with a cropped pant the next time you’re unsure of yourself.

*Disclosure: This post may contain affiliate links, which means that I get a commission if you decide to make a purchase through our links, at no cost to you.

Where can I find the best cropped pants?

I would like to start off by sharing some great ankle pants options if you’re on the hunt for a good pair which could be as versatile as your lifestyle.

First on the list are these high-waisted skinny ankle pants from Old Navy. They are very affordable and come with thousands of rave reviews which is always a great thing to see when shopping online. They also come in a range of great neutral colors which would allow you to mix and match with different tops and sweaters to create many different outfits.

If you’re looking to build a more casual look featuring cropped pants, I would recommend you try a pair of cropped skinny jeans such as these ones. Cropped jeans are the perfect jeans to pair with ankle boots in the fall because you won’t need to tuck anything in as the boots would hit right where your jeans end. I talk more about this on my post HERE.

Spanx now has a great pair of pull-up ankle pants you can now take from the boardroom to vacation in the Hamptons. These skinny ankle pants are a great option of cropped pants you could wear with either ballet flats or high heels. Although they are a little on the pricier side, the reviews say they’re worth the extra coins.

If ankle pants in a relaxed fit and rich color are your thing, then you must checkout this pair from ASOS. I hope by the time you’re reading this post it’s still available but I love the green color, tie front belt and of course…the pockets! They’re more of a lightweight pair of pants and so I would stick to wearing them in the Spring, Summer and early Fall.

Now that I’ve shared some great websites you can browse to find a great pair of ankle pants, let’s talk about styling them. The type of shoe you choose to wear with your ankle pants is really the determining factor in how your overall look would come together.

1) A pair of ankle boots

As mentioned several times on this blog, ankle boots are the best shoes to go with anything ankle-length. That’s because they typically hit the ankle bone right where your pants or skirt reach. You could style a pair of ankle jeans with Chelsea boots and a bomber jacket to create a fall look with a casual vibe.

Get the look HERE

Another look I love is pairing Chelsea boots with cropped ankle pants, a sweater and a trench coat to top it off. If you want your outfit to be more dressy, try a pair of heeled ankle boots and add a longline coat to really elevate your look.

2) A pair of ballerina flats

Ballet flats are a great way to style a pair of ankle pants or jeans in a business casual manner. My personal preference for more formal occasions is to go with a pair of pointed toe flats. Choosing flats in a neutral color is also a great idea if there’s a lot going on with your pants and sweater in terms of bright colors.

Get the look HERE

Consider pairing your ankle chinos with a simple top and a flat shoe for a more elevated summer causal look. During the fall, replace the top with a long-sleeved sweater and throw on a jacket to complete this chic fall look.

3) With a pair of sneakers

Let’s face it, sneakers and anything are a thing now. You can find sneakers being paired with skirts and dresses as well as jeans and pants. Create a chic casual vibe by pairing classic white sneakers with a pair of culottes and a simple shirt. You could add a denim jacket to this look if it’s a little cold outside.

Get the look HERE

Another way you can create a nice and simple ankle pant + sneaker look is by opting for a pair of chunky sneakers. I like how chunky sneakers make the rest of your body look so much smaller in comparison. The chunky sneaker look works with both denim as well as more formal pants. It could even be your in-between footwear that you switch up when you get to your destination. That’s what I call commuting in style.

4) With strappy sandals

Strappy sandals are the perfect shoes to pair with your ankle-length pants when you’re going for an elegant look. Choose a soft and sexy top if you’re styling this look for date night. If you’re headed a for a more formal event, a white blouse (or in any solid color) would make for a great top.

Image source here

Another way to style ankle pants with strappy sandals is by wearing a crop top. This look works best if the ankle pants are high waisted. Don’t forget the earrings and shoulder bag to complete your look.

5) With a pair of knee-high boots

During the colder months, styling a pair of ankle length pants with some knee-high boots is a great way to keep both warm and stylish. It would be easiest to go with wide-leg pants in this case just so it’s easier to get the boots on and not have to worry about tucking them in. You could definitely go with a pair of cropped straight leg jeans as well but just know that this is the more casual option. You could top your look off with a leather jacket to add some sass.

Get the look HERE

Feel free to have fun with your choice of boots and try a pair of sock boots if you never have. They don’t tend to reach all the way up to your knees but have a higher shaft than the average ankle boot.

6) With platform shoes

Nowadays, platform shoes could be sandals, loafers or even flip flops. They’re a less formal and more comfortable form of heel that you can pair with your ankle pants and jeans depending on your personal style and the occasion you’re dressing for. I like to go with platform sandals if I’m headed somewhere very informal like a pool party or brunch with the girls.

Get the look HERE

The platform loafers or platform heels could be worn to work with a pair of ankle wide leg pants and a simple sleeved top. We all know the platform flip flops are to be saved for a day at the beach, a casual barbecue, or a brief walk around the block.

7) With a pair of high heels

There’s no way this list would complete without the heels! We’re talking kitten heel pumps, strappy heels, stilettos or regular pumps. I personally like to choose open toe heels for fancy occasions such as birthdays, dinner dates and galas. I like to save the pumps for more business events, but these could definitely be paired with ankle length boyfriend jeans and a cute top for a more edgy look.

Get the look HERE

If you have short legs, heels and cropped pants are your best friend. The combination of the cropped pant and high heel would make you appear even taller.

I hope you have come to see just how much your shoe styles influence your entire ankle pant look. The type pf pant you choose would heavily influence your shoe choice as some fabrics are much more casual than others. There is bound to be a look that goes with your personal style on this list, and I hope you have found it useful.

Do let me know which one of these shoe choices was your favorite and which one I may have missed.

If you need some guidance styling a pair of brown pants, check out my post: 12 Shoe Colors to Pair Perfectly with Brown Pants for some guidance.

Looking for ways to wear your jeans with running shoes? Check out this post HERE

If you're looking for some more ways to style your ankle pants for the next season, check out my post: 12 of the Best Shoes to Wear with Ankle-length Pants.

Until the next post,



bottom of page