The Ultimate Guide To Matching Your Shoes To Your Jeans

Guide To Matching Shoes To Jeans

Ugh - The What Shoe Goes With What Jean Challenge

The good news is that jean styles have evolved, and we as consumers have options… lots of them, actually. Because there is not just ONE particular style of denim that is dominating the fashion landscape, we can, hurray, hurray, pick what style is most flattering for our figure. And have multiple styles in our wardrobe arsenal to choose from.

The bad news is that what shoes to pair with what style of jeans then becomes a major challenge. Because the silhouette of the jean directly impacts the shoe choice, finding one that plays nicely with it is not always easy. It can feel like an ever-elusive search to find the right match.

But never fear - I’ve got you covered. Here’s a handy dandy guide that breaks it all down. And with each silhouette, I’ve given you both heeled and flat options to pick from. Because ladies, It’s our prerogative to change our minds (and to look flipping fabulous while doing so!)


What Shoes To Wear with Skinny Jeans

Skinny jeans have been our ride-or-die when it comes to form-fitting denim. And they are still a classic, so don’t worry about what gen Z is saying…If you love them, you should wear them. And there are ways to rock your skinnies that can feel current and modern.

Because skinnies hug your body in all the right places,  you'll want shoes that complement their sleek silhouette. Lug sole booties, retro sneakers, chunky loafers or stilettos all work! These shoe styles will help flaunt your figure while keeping your look on point by adding some visual heft below your ankles to balance out the skinny silhouette. Trust me, you can't go wrong with this combo!

If you’re looking to modernize your skinny jeans, opt for an ankle boot that fits under your jeans instead of over them - it will make all the difference.


What Shoes To Wear with Straight-Leg Jeans

Straight-leg jeans are like the cool cousin of skinny jeans – they have a looser fit but still give you that slimming effect we all love. This jean style is the perfect first pair to help you move away from your skinny jean habit. You can rock chelsea boots, high top sneakers, or fisherman shoes with this jean style. These shoes perfectly complement the effortless vibe of straight-leg jeans, giving you that "I just threw this on, but I still look amazing" feel.

I’ll go out on a limb here and even say the straight leg jean is the most versatile style of the moment - they tend to go with most shoe styles, so you can’t go wrong.


What Shoes To Wear with Bootcut Jeans

Bootcut jeans were made for, well, boots! These jeans flare slightly at the bottom, creating the perfect space for your favorite ankle or knee-high boots. Slip on a pair of these bad boys, and you'll be rocking a chic look that's perfect for work, a night out, or just strutting down the street.

The truth is this jean style works best with some heel (like a pump) - the angle created when wearing a heel perfectly complements the boot cut. However, if you’re not in a heel mood, opt for a shoe that has a pointy toe to help balance the flare. Pointy-toe flats or even a barely-there sandal work well.

what shoes to wear with bootcut jeans

What Shoes To Wear with Boyfriend Jeans

We all have those days when we just want to be comfy and casual – that's where boyfriend jeans come in. With their relaxed, slouchy fit, you'll want shoes that match their easygoing vibe. Try pairing them with sneakers, loafers, or sandals for a laid-back look that's still super stylish.

Boyfriend jeans can also work with a pump to dress them up - it goes back to the rule of juxtaposition and is a gem of a styling tip to up level your outfits.

what shoes to wear with boyfriend jeans

What Shoes To Wear with Wide Leg Jeans

Wide-leg jeans are a statement piece that can be dressed up or down, depending on the occasion. For a dressier look, heeled sock boots, ballet flats, or pointy-toe pumps work well with this silhouette.

Heeled sock boots provide a streamlined look that accentuates the wide leg, while ballet flats create a more relaxed, effortless vibe. Pointy-toe pumps create a chic and sophisticated look that adds some height and structure to the silhouette.

The key to making this style work is to see the shape of the lower leg and ankle, especially with a cropped wide leg. Visually, there must be a significant difference between the jeans and the leg’s width. Naturally, this occurs. A boot that is tight to the ankle, like a sock bootie, is ideal because it highlights the width differential.

When wearing full-length wide-leg jeans, having a more pointed shoe than round helps the wider silhouette feel proportioned instead of bottom-heavy. This denim style is ideal for women who are more triangular in their body shape, as it highlights the waist and camouflages the hip and thigh region.

what shoes to wear with wide leg jeans

What Shoes To Wear with Crop Flare Jeans

Crop flare jeans are a modern option that can be styled in many different ways. Sock booties, pumps, or sandals work well with this denim shape. Sock booties create a seamless transition between the shoe and the hemline, while pumps add height and structure to the silhouette. Sandals can create a more casual and relaxed vibe, perfect for a warm summer day.

The thing to keep in mind with cropped pants is that the shoe becomes more important. Think of it this way… the shoes are on display when the pants are shorter. And this is not a bad thing, at all! It’s actually a wonderful styling opportunity.

There are two things to keep in mind when picking your cropped jeans/shoes combination. First, the jeans should, in a perfect world, hit at the ankle bone. That is the most universally flattering and versatile point of the leg. It can be shorter, however, it should hit below mid-calf, between where the calf tapers and the ankle bone. 

Second, when choosing shoes for crop flare jeans, try to keep the hemline in mind and aim for shoes that won't cut off the leg line at an awkward spot. Having a bootie that is higher in the shaft and goes fully under the jean is the best way to create this seamless line. Additionally, having a shoe that shows more skin on the top of your foot, the vamp also achieves this visual cohesiveness.

what shoes to wear with crop flare jeans

I hope these tips for matching shoes to jeans have made this otherwise daunting process a little more digestible and achievable. My overarching goal is to empower you to create stylish and cohesive outfits that flatter your figure and show off your personal style

Whether you prefer skinny jeans, straight-leg, bootcut, flared, wide-leg, or crop flare, there is a perfect shoe out there to complement your favorite denim. So, experiment with different styles, have fun, and step out confidently, knowing you have found the perfect match.

Jean and Shoe Pairing Guide
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