How to Wear Ankle Boots with Jeans

I’m so excited to share an update to my most popular post EVER today! Ankle boots are the most popular footwear choice in the fall and winter, and jeans are our most popular clothing item. It makes sense that figuring out how to wear the two together would be important. Let’s dig into how to wear ankle boots with jeans!

I’ll be breaking down how to wear ankle boots with ankle length skinny jeans, straight leg jeans, cropped skinny jeans, and long skinny jeans. We’ll talk about what type of boot works with each style of jean and why! The main thing to keep in mind is that you do not want a huge gap of skin showing between the top of your boot and the bottom of your jeans and/or you do not want your jeans to bunch up a lot on top of your boots.

How to Wear Ankle Boots with Ankle Length Jeans

Let’s get started! I thought I would pick my favorite pair of jeans first and the most common style – how to wear ankle boots with ankle length skinny jeans. By this I mean a standard pair of skinny jeans that hits at or just above your ankle. I am wearing the Abercrombie high rise super skinny jean. It’s a great pair of jeans. Runs true to size, stretchy but doesn’t stretch out. My go-to pair. The regular length hit about an inch above my ankle bone, and I am 5’10. Definitely order the short if you are shorter than I am.

When wearing this length of jean, you usually want to go for a boot with a shorter or mid-shaft style boot. In the first photo I am wearing the Target classic boot. Lower shaft and lower heel. Super comfy and easy to wear! In the second photo I am wearing the same jeans and a similar boot that doesn’t have much of a shaft. Here is the current version. You can wear a taller boot too. The goal is to show either a little skin or just let your jeans and boots meet with this combo.

How to Wear Ankle Boots With Cropped Jeans

Since cropped jeans are by nature a shorter length, you need a taller boot here. It’s a little harder to tell with my mirror selfie, but this is the same pair pictured at the very bottom of the post. It’s my tallest shaft boot and pairs perfectly with a more cropped pair of denim. Bot my boots and denim are older here, but these jeans are the AG Farrah in the cropped version.

How to Wear Ankle Boots with Long Jeans

Below are my longest pair of skinny jeans, the Madewell classic skinny jean in tall. When not rolled, they come to the top of my foot. In the first photo I am wearing them with my all time favorite ankle boots, the Marc Fisher Alva. They are definitely a splurge pair, but you can use my code LTD2107 for a 20% discount. They come in all colors, leather, and suede. Since this boot has a taller shaft AND my jeans are long, I needed to roll the bottom of my jean up just one time. Simply cuff the bottom of your jeans up one time.

In this photo, you can see how you would style these jeans differently when wearing them with a different pair of boots. This pair of boots has essentially no shaft at all which means the top of the boot and the bottom of the jeans just come together. The perfect pairing! There is no need to do anything! Here is the current version of the boots I am wearing.

How to Wear Ankle Boots with Straight Leg Jeans

Possibly the trickiest of all, let’s talk about how to wear ankle boots with straight leg jeans. If you are really interested, I have a whole post on this topic that goes into a ton of detail about what makes this work! My recommendation is to look for a straight leg pair of jeans that is NOT too wide and that goes just above your ankle bone. If you buy a pair that actually flares out as it goes down as opposed to being totally straight or slightly narrowing, it gets tricky to pair with boots. You also want the inseam to be longer than you might think. 1-2 inches above your ankle bone is ideal.

Here I am wearing the Abercrombie high rise ankle straight jeans in the tall. I ordered the regular, and they were too short on me. The long was a tad too long, so I cut them to be right where I wanted. Find the right pair for YOUR body. It can take some searching. My other favorites are anything by Madewell in the Stovepipe or Perfect Vintage (second photo). A more budget friendly option are the Old Navy OG straight or Power Straight. I prefer a boot with a slightly taller shaft so that your boots and the hem of your jeans just almost meet. You don’t want a huge skin gap showing. Especially if your jeans are shorter, opt for a taller bootie. See examples below.

How to Wear Ankle Boots with Jeans Recap

I hope that helps clear up how to wear ankle boots with jeans. Really it all depends on the length of your jeans. You want to pick your boot height based on where your jeans hit your leg to prevent too much skin from showing. If this post was helpful to you, please consider sharing and pinning!

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