What shoes to wear with skinny ankle length pants blog graphic

Gotta love a good bit of style inspiration. In a follow up to What is the difference between ankle boots & booties? Here is the promised “what shoes to wear with skinny ankle length pants.” 

We’re going to break this down into two parts. First, what shoes to wear with skinny ankle length pants in general (with inspiration photos). Second what shoes to style with skinny ankle length pants for you.

What shoes to wear with skinny ankle length pants examples graphic
Scroll down for larger examples. Images via Unsplash.

What shoes to wear with skinny ankle length pants IN GENERAL

When styling a skinny ankle length trouser I lean towards a shoe that keeps a bit of space between the hem and the shoe. This could be a shoe like a ballet flat or mule. Or low cut sneakers, heels or boots.

Alternatively if the pant is on the looser end of skinny, you can go with a tight fitting boot that fits under your pants and still defines the ankle. Or go the exact opposite direction with a very tight fitting skinny pant that fits inside your boot. 

If the pants you’re styling are jeans, then chunkier sneakers and boots are also great options. 

Basically, you can wear any shoe you want with skinny ankle length pants, if you style it right. 

But whatever shoe you choose, don’t forget, if you’re styling your pants with a higher cut shoe (like an ankle boot) keep an eye out for unintentional cuff bunching. If you have cuff bunching, you want it to be intentional. 

And keep reading for help figuring out what shoes to style with skinny ankle pants for you.

What shoes to style FOR YOU

While pretty much any style combination of clothing could work in theory, the key to building and keeping a wardrobe you love is finding the combinations that work for you. Because that’s what personal style is.

So when you’re looking for shoes YOU should wear with skinny ankle length pants ask yourself: 

  1. What styles of shoes do you currently wear? If you wear any of the above shoes, start there.
  2. What types of shoes are comfortable for you? Being comfortable and confident in your clothing is one of the keys to personal style. So are any of the shoes you’re comfortable in a style that works well with skinny ankle length pants? If so, start there. 
  3. What’s the general vibe of your personal style? If you’re still here and neither of the previous questions spark a pant/shoe combination that you want to try, what is your reason for wanting to try styling skinny ankle length pants? 
    • If you’re wanting to play with a new style for fun and to see if it works for you – choose one of the general style options and have fun!
    • But if you’re asking because you feel like you “should” – give a general style option a try. Also remember that personal style doesn’t come from wearing what you “should” wear.

(When you’re expanding or figuring out your personal style, these are the types of things it can be really helpful to keep track of in your wardrobe inventory. In fact, it’s one of the example areas I call out in The Wardrobe Inventory Workbook, decide if building a wardrobe inventory might be helpful.)


And there we have it – what shoes to wear with skinny ankle length pants, both in general and also for you!

This post was prompted by a question I got asked. If you want your style question answered, submit it right here!