pair shoes with pants

The Ultimate Guide To Pairing Shoes With Different Pant Styles

Remember last time, we chatted about the longevity of skinny jeans? And the fact that some newer pant styles, with wider legs, are making their way onto the scene? And do you also remember that I said because of this shift, there’s an ongoing conflict about what shoe or boot to pair with these wider leg styles?

Well, this week, I’m addressing that very issue. It’s a subject that’s been coming up over and over again with clients, blog readers, and social media followers too. And for good reason. Shoe and pant combinations are an area many people struggle with. Even before the shift toward wider pant styles, it was challenging to know what shoes to pair with pants.

When the pants and footwear of an outfit are out of sync it feels off. It’s like having Froot Loops and filet mignon at the same meal. On their own, or in a different combination, they’re fantastic. Together, not so much. There’s an incompatibility.

Why is the shoe/pant situation so difficult? Well, for a few reasons…

  1. Shoes can make or break an outfit – a great ensemble with the wrong shoes is a big ole miss.
  2. Practicality matters. Shoes need to be walkable in and often the more comfortable a shoe is, the less pretty.
  3. There’s a direct connection between your shoes and the pants you’re wearing, they need to work together. Both in proportion and in the genre. Now that does not mean you need to dress in costume, but it does mean that there should be a harmony amongst the pieces. 
  4. The combination of shoes and pants is not only the foundation of an outfit but also the focus of the optical illusion that creates length and height
  5. Combined,  pants and shoes take up almost ½ of the body real estate, so it’s important they play nicely together..

How do you figure out what shoe goes with what pants?

One of my favorite exercises to do with styling clients is to create a photo album for them of the shoes that work with particular pants. And from the feedback I receive, clients find this very helpful! That way when it comes time to get dressed, they can start from the bottom up. 

pair shoes with pants

Typically that’s not how people go about putting together an outfit. But when you turn the equation around, you’ll know what 2-3 pairs of footwear coordinate with a pair of pants. Putting together the rest of your outfit will be a piece of cake!

Your Personal Cheat Sheet – The Shoe/Pant Formula

This explanation is way better suited for a video than the written word. Partly because it’s so visual, and partly because I’d always rather talk than type.  I’m going to give you an uber detailed description. I will be outlining what style of shoes pair nicely with what type of pant. And if you’re more of a visual learner like me, I will also be adding a video to my Instagram story to illustrate the formula.

The general rule to remember is this: The wider the pant leg – the slimmer the shoe profile should be.

By shoe profile, I mean the definition around the ankle (aka slimness in the shaft) and the pointiness of the toe. A round toe ballet flat might work with skinny jeans (slim) but looks quite squatty when paired with a culotte (wide) style jean.

So too, all ankle booties are not created equal. Clunkier booties, those that have a lower shaft height and a wider ankle opening (think of an engineer or moto boot) look good with a skinny jean because the jean sits inside the boot. But not with a straight leg, kick crop, or wider style because those wider legs sit outside or on top of the boot shaft. The heaviness of the boot helps ground a skinny pant but gives the illusion of a tree trunk leg when combined with a straight leg look.

The Ankle is Key

Seeing ankle, whether the actual bare ankle or the illusion of it with a fitted bootie, is what allows these wider jeans styles to look attractive. There needs to be visual differentiation between the volume of the pant and the delicateness of the leg/foot. Otherwise, it can feel very bottom-heavy.

There are three styles to look for to pair with the wider leg jean styles:

1. Sock booties

2. Pointy-toe pumps (or flats)

3. Ankle-strap sandals

Popular Pant Styles and What Shoes to Wear with Each Style:

Straight leg: The most versatile style. This pant leg works with most shoes and looks particularly modern with a sock-style bootie because the boot will fit under the jean but there will be room on the sides to see the smallness of the ankle.

Cropped kick: Looks great with a pointy toe or a sock bootie because the width at the bottom of the pant needs the juxtaposition of the slim ankle to really shine. This style does not really match well with a chunkier boot.

Boot cut or flare: These look best with a pointy toe pump or even flat. The narrow toe box helps achieve a delicate balance to the wide cuff of the jean.

Boyfriend: The slouchy nature of this jean allows it to work with most shoes. However, combining this style with a more feminine shoe, particularly a heel, elevates the whole outfit by playing the feminine off of the masculine.

I know this is a lot to take in, and you may need to refer back to this article a few times before you truly get the hang of what shoes pair well with what pants. But I hope that this brings a little clarity to the whole pants/shoe debacle. As trends change and styles come and go, my goal is to stay a few steps ahead of you (in my well-paired shoes) to guide you through the ever-changing world of fashion. 

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Since the purpose of this blog is to take the stress out of getting dressed, we try to make it easy on you by sharing shoppable links (accessed by clicking the PINK words or the actual photo) with awesome readers like you. We want to let you know, some of those contain affiliate links for products. There is absolutely no additional cost to you if you take action (click, purchase, subscribe) with one of these links. As a result, we will earn some coffee money from your click.  But we promise to drink it while creating more ad-free, helpful content like this.

Photo: Becky Cormell



Cleveland-based personal stylist and fashion blogger.

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