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We all know that a classic pair of boots and a solid pair of jeans are wardrobe essentials. And we even all know that they look great when worn together. But what’s a little less known is how to wear them together. How tall should the boots be? How short should the jeans be? What’s the right style for both? Is there some sort of magic formula that ensures the right look every time? If these questions have been swirling around in your head and you’ve been wondering how to wear ankle boots with jeans, I broke down the different looks to a math formula (I got out the tape measure and all) and put together this ultimate style guide!
What to Know About How to Wear Ankle Boots With Jeans
Before we get into all the different ways to wear ankle boots and jeans, it should be mentioned that a lot of this is based on personal preference, your own unique personal style, and how you like to wear your jeans.
I know this can be confusing to those who want to know whether or not they’re wearing something the “right” way, but when it comes to fashion, there really are no hard rules. There are guidelines, but ultimately, you should wear what you like and feel comfortable in.
This post can give you the tips and tricks and visual examples needed to pick the right choice for you – because sometimes you’ve just got to see it to know if you like it or not!
But with that being said, jeans and boots belong to my signature outfit combination, so I’ve experimented a lot. (When I die, bury me in a blazer and basic t-shirt too, please.) And though I’m not a trend-focused person, part of my job is knowing “what’s out there”, and after 6+ years of studying various looks, this is what I think works.
Okay! Let’s start with the jeans styles. I picked four major styles that almost everyone has in their wardrobe (or should):
Spoiler alert: These are, in my opinion, one of the best types of jeans. There are slight differences between slim and straight-leg jeans, but for the most part, they are pretty similar, so most of these rules can work for both.
Have a pair of mom jeans instead? Mom jeans are classified by the waist, hips, and the way they fit. Most mom jeans have a slim ankle cut, so it’s possible you can use these styles interchangeably too.
In this post, I’m wearing straight jeans from Madewell’s The Perfect Vintage Straight Jean Line. Definitely recommend!
It’s true, they are not the most current style of jeans anymore. If you’re wondering what’s “in”, wide-leg, flare, and looser, baggier jeans are popular. However, skinny jeans can still serve a purpose.
In this post, I’m wearing an older pair, but these look really similar.
Similar to bootcut jeans and how they flare at the end, these are shorter (cropped) and are a more current version. You may also see these go by demi-boot, crop flared, flare cropped, etc.
In this post, I’m wearing an older pair, but these look really similar.
Instead of flaring out at the end, these have more of a general roomier fit on the legs, while still being fitted around the waist and hips. They are not supposed to be baggy.
In this post, I’m wearing Everlane’s Way High Jean. They are technically not wide-leg jeans, but that is how they fit on me. However, here is their version of a true wide-leg jean.
When building your jean collection, stick with denim jeans of varying washes. Blue jeans are going to be the most classic and it’s helpful to have them in a light, medium, and dark wash to cover different seasons and occasions.
Once you’ve got those covered, black and white are the next helpful and classic colors to have. Regarding what’s trendy, different colors will always come in and out in popularity, but neutral ones are the best ones to have first.
Now, onto the boots:
Ankle boots, ankle booties, calf boots – these are all used interchangeably by retailers and stylists alike, but there are slight differences. For this post, we are classifying ankle boots as boots that end at the ankle (sometimes called a bootie).
In this post, I’m wearing Everlane’s The Day Boot. These ankle boots are an investment and they cost more now than what I paid for them, but I think they’re worth every penny. I’ve worn these for years and they are my favorite pair of black boots. They’re about as classic as you can get.
Sometimes calf boots fall under the ankle boot umbrella. But these taller boots have a higher shaft, so to differentiate for the sake of this post, I’m calling them calf/mid-calf boots as sometimes they’re advertised as mid-calf boots too.
In this post, the ones I’m wearing are old, but these look really similar.
Whether a block heel or stiletto heel, this style of boot is classic and can always style a chic look! Though lately, cowboy boots have taken their place. Personally, Western boots don’t make the timeless fashion cut to me (as it’s hard to style a classic look with them), but it doesn’t mean it’s wrong to have a few trendier styles for a more modern look. (Just focus on the wardrobe essentials first.)
if you have a pair you’re trying to style, these tips can be shared, assuming your cowboy boots are tall boots. Though the styles are different, the shaft of the boot usually fits the same as wider knee-high boots.
In this post, the ones I’m wearing are old, but these look really similar.
In 2024, these boots are not as popular anymore. However, if you have a pair and like them, there’s no use throwing them out! Though they’re not as timeless, they do have more of a casual look. (And living in the midwest, I think they’re a pretty practical shoe).
In this post, I’m wearing Sam Edelman’s Waterproof Platform Boot.
Sock boots are not the current trend (if that matters to you), but I think they’re one of the best boots to wear with almost all types of jeans. Because they fit like a sock, they take a lot of the guesswork out of knowing what jeans to pair with them. As long as the jeans have a wider-leg opening than the sock boots, you’re good to go.
In this post, I’m wearing Everlane’s Glove Boot and I highly recommend them!
This is a classic style that has seen a lot of reiterations. If you have a taller pair, then the height is similar to combat boots and these tips could work for those as well.
In this post, I’m wearing Sam Edelman’s Laguna Chelsea Boot.
As you start to build your boot collection, make sure you get different colors. No, not pink, orange, or purple, but brown, black, and varying shades of beige. You’ll find that you can wear and style these colors the most. Then if you want to get a few fun colors and prints, feel free!
Okay, now that you’ve got the shoe and jean overview, let’s get technical, technical.
STRAIGHT-LEG JEANS
Starting with my favorite pair of jeans, straight-leg, let’s see what works. As you can see, the majority of the classic boot styles work, which is why this is one of the best styles of jeans to have in your wardrobe.
They are a great option to wear with almost every major boot style, but one style specifically doesn’t work as well: knee-high boots. If you’re wearing taller boots over bottoms, then it should have a seamless fit. Straight/slim jeans are not skinny, tight, or fitted enough.
CROP FLARE JEANS
Crop flare jeans are probably the second best option to wear if you’re wondering how to wear ankle boots with jeans. As you can see, most shoe styles work, except once again, taller boots do not.
Because crop flare jeans have a flare and not a wide leg, there is not enough room to wear tall boots under and they are not seamless enough to wear over. Both scenarios create weird lines, bulges, and unnecessary bulkiness.
When it comes to pairing this jean style with heel or flat ankle boots, the best way to ensure that it looks good and not awkward is to keep the hem of your jeans 1/2 inch to 1 inch (ideally) above your jeans, measuring at the top of the bootie.
Any lower than a 1/2 inch and your jeans could start to get stuck in your pair of ankle boots. Any higher than 2 inches and the proportions look off, almost like you are wearing capris with boots.
To sum up: A good rule of thumb for crop flares and ankle boots is that your jeans slightly graze your boots by 1/2 inch OR the jeans hang past your boots.
SKINNY JEANS
Currently, I rarely wear skinny jeans, and if I did, it would be with knee-high boots. But if you still want to wear your skinny jeans with ankle boots, you have some different options. Depending on how long your skinny jeans are, you may need to find a way to make the meeting of jean and boot aesthetically pleasing.
Options:
- Tuck your skinny jeans into your boots
- Fold the skinny jeans under to create a cleaner break
- Single cuff
Cuffing them is my least personal favorite option as I think it’s dated and it reminds me of this girl:
If your jeans will stay, I think folding the jeans under can be a great way to still wear this jean style if that’s what you want.
WIDE-LEG JEANS
Because wide-leg jeans have a wider leg opening, it makes wearing ankle boots a lot easier! With this jean style, your boots need to go under without being too tall. Be careful of ankle boots/ booties as you don’t want the hem of the jeans “meeting” the boots because they can get stuck when you walk.
We covered a lot of dos and don’ts. In a nutshell, here’s what I think doesn’t work:
And here are visual examples of what does:
And if you need an easy graphic to pin without my face in it (aww why not), then just tap the picture if you’re on mobile:
That’s a lot! Let’s summarize:
- The easiest (and most current) way to wear ankle boots with jeans is the following jean styles: Straight leg jeans, crop flare jeans, or wide-leg jeans. You can create many different outfits out of these jeans.
- Boots with a heel can give you a more polished look. (Stiletto high heel optional.)
- My favorite way to wear ankle boots with jeans? If I had to pick, I’d choose these combinations, but it’s certainly not my only favorite: straight jeans + ankle boots and crop flare jeans + ankle boots
How to Wear Ankle Boots With Jeans: Perfected
The fall and winter season is the perfect time of year to wear ankle boots with jeans. Now that you have these wardrobe essentials, it’s time to build the rest of your fall wardrobe, so you can be ready to style your best outfits this time of year. Learn how in How to Build the Perfect Fall Capsule Wardrobe (With 100 Outfit Ideas)
