The following content may contain affiliate links. When you click and shop the links, we receive a commission.
When it comes to fall fashion, one of the most common outfit combos is jeans and ankle booties. Jeans are the obvious pants choice for the fall: They’re warm, flattering, and comfortable (if you have the right pair) and look great with almost any top. Booties are loved for similar reasons: They’re warm, flattering, and comfortable (again, assuming you have a good pair) and look good with most styles of jeans.
However, not every pair of jeans looks good with every pair of booties. Some booties look better with jeans tucked in or just kissing the hem, other booties look better when your jeans cover the top of them, and some look best with jeans that cover the shoes entirely. In today’s post, I’ll break down what booties to wear with what style of jeans, so if you’re struggling to style yours, I’ve got ya covered.
Ways To Wear Ankle Boots With Jeans In The Fall & Winter
I debated how to approach this post. At first, I thought I’d break down each style of jeans and discuss what booties work with them, but then I realized that you’re likely reading this post because you already own booties and aren’t sure how to wear them. So, below, I’m outlining the most common styles of booties so that you can quickly scan to find the pair you have and then share how to style them.
What are the different types of booties?
This is a great question. There are a ton of booties on the market, and it’s almost impossible to put them into three or four categories. But for the sake of this post, I’ll break booties down by “shaft height,” meaning the height of the part of the bootie that goes up your ankle. I’m outlining the post this way because I find that the shaft height determines the style of jeans I wear. I know that not every style of bootie will fall into these categories, but I hope you’ll find each section helpful to apply to other styles.
High Shaft Booties
High-shaft booties typically come in two different styles: tight up the ankle or more of a wide-shaft.
Narrow ankle
The best way to style tight-ankle high-shaft booties is with a wider pair of jeans. It’s difficult to tuck any style of jeans (even super skinny) into ankle booties with a tight shaft since it starts to look messy. Instead, wear them underneath mom jeans, wide-leg jeans (cropped or full-length), or boyfriend jeans. The top of the ankle won’t show unless the jeans are cropped, and that’s okay.
Wide ankle
A wide-fitting high-shaft ankle bootie gives you a little bit more flexibility when tucking your jeans. This style looks great with super skinny jeans if you tuck them into the booties because the wide shaft makes room for the jeans while the jeans still give you a flattering look near the ankle. Since they have a wider profile, I avoid wearing this style of booties with mom jeans, wide-leg jeans, or boyfriend/straight jeans. While the booties themselves aren’t bulky, they do not define your ankle at all and, therefore, aren’t quite as flattering with relaxed styles of jeans.
Mid-shaft booties
The majority of the boots that I own are a mid-shaft. Like tall-shaft boots, you’ll find both narrow-ankle and wide-ankle options. This style of booties (specifically with a heel) are the most versatile in my closet.
Narrow ankle
Narrow-ankle mid-shaft booties typically look best with skinny jeans. You can tuck your jeans into the boots, wear cropped skinny jeans that just skirt the top of the booties, fold a tiny cuff in your skinny jeans so they sit right above the booties, or even roll your skinny jeans under so that your new “hem” just barely touches the booties. You can also style these booties with wide-leg jeans, mom jeans, kick-flare, boyfriend, and straight jeans. The bootie’s narrow-ankle fit helps to balance the wider, relaxed leg of these denim styles.
Wide Ankle
For wide-ankle mid-shaft boots, you can also pair these with skinny jeans. Again, you can tuck, roll, cuff, etc. However, with a mid-shaft bootie with a wider ankle, avoid wide-leg jeans, mom jeans, boyfriend jeans, and straight jeans. Since these booties have more “bulk” to them, they don’t balance relaxed jeans as well. A great example of these booties is Chelsea boots. They are great with skinny jeans but since I don’t own skinny jeans at the moment, I wear them most often with leggings.
Low-shaft Booties
Again, these booties with a lower shaft generally come in a narrow ankle style or a wider ankle.
Narrow ankle
They look great with skinny jeans, but they aren’t flattering tucked in. If you try to tuck jeans into low-shaft booties, you’ll end up with a messy, bulky ankle. Instead, make a narrow cuff or roll them under so that the jeans hit right where the booties start. They look perfect under wide-leg jeans, mom jeans, boyfriend jeans, and straight jeans, too.
Wide ankle
Wider ankle low shaft booties are versatile but more complicated to style with wide-leg/mom jeans, etc. These are better worn with skinny jeans the same way the narrow ankle low shaft booties – jeans rolled under or cuffed, but not tucked in.
In general, I’m not a big fan of low-shaft booties as someone who’s 5’1″. They tend to shorten my frame rather than elongate it!
Final Tips for Styling Jeans with Ankle Booties
- Consider proportions: Always think about the length of your jeans and the height of your ankle booties. You want the two to complement each other without any awkward bunching or cutting off the line of your leg. The goal is to elongate your legs when possible.
- Experiment with textures: Play with different materials. Leather or suede ankle boots can add a touch of luxury to denim, while textured jeans (like ripped or distressed) can give a more casual, edgy vibe.
- Add layers: To elevate your look, throw on a stylish coat, chunky sweater, or oversized blazer to finish your outfit.
In the end, finding the right pair of jeans for your ankle booties is all about balance, comfort, and personal style. I don’t believe in rules when it comes to fashion, so wear whatever feels cutest to you!
Shop The Post