Wearing ankle boots with jeans is a classic, stylish choice that never goes out of fashion. However, it’s important to style them correctly, as not all jeans work well with ankle boots. In today’s guide, I’ll share some essential tips on how to pair ankle boots with jeans for a look that’s always on point. Whether it’s choosing the right cut of jeans or coordinating colors, these tips will help my you look effortlessly stylish every time.
If you’re searching for that perfect pair of jeans, check out my Denim Fit Guide where I share my favorite types of jeans, sizing, and more. And for more of my favorite fall boots, check out my post here.

How to Wear Ankle Boots with Jeans
Choose the Right Jeans Cut:
When selecting jeans to pair with ankle boots, consider the occasion and your personal style. There are many different types of jeans to choose from. Skinny and darker wash jeans are my go-to for a sleek, sophisticated look, perfect for dressier events. Pairing booties with Straight leg jeans offer a classic, versatile style that works for both casual and elevated settings. Cropped jeans are great for a more playful, modern look. And they’re a great way to showcase your ankle boots. Bootcut Jeans paired with ankle boots create a classic, balanced look, adding a touch of retro flair to your look. And wide leg jeans can create a modern statement, ideal for trendier occasions.
There is no perfect answer, however, I share some of my favorite ways to style ankle boots with jeans below, which will hopefully help to inspire your wardrobe. Also, don’t forget you can always cuff your jeans, especially straight leg or wide leg styles, to adjust their length and make your ankle boots stand out.
Don’t be Afraid to Cuff Your Jeans:
If you’re wearing jeans that are a bit longer, don’t be afraid to cuff them. A good place to cuff them is neatly just above or at the top of the boots. This adds a stylish touch and prevents bunching. However, avoid cuffing your jeans too high above the boot, because it can make your legs look shorter.
Try Different Boot Styles:
Try experimenting with different boot styles, like Chelsea boots, booties with a heel, or flat moto boots. Ankle boots can easily dress up a casual pair of jeans or add an edge to a more polished look. Rugged boots pair well with distressed jeans, while sleeker, heeled boots complement cleaner jean styles. The height of the boot’s heel can change the look and feel of the outfit too. For example, higher heels can dress up the look, while flat boots are more casual.
Keep the Occasion in mind:
Choose your ankle boot style based on the occasion. More polished or heeled boots are great for dressier looks, while flat or rugged styles suit casual outings. The shaft of the boot is also important. A higher shaft ankle bootie can look great with skinny or cropped jeans because they elongate your legs. Meanwhile, knee high boots work best with skinny jeans that tuck smoothly into them for a clean line.
Remember, fashion is also about personal expression. The most important thing is that you feel comfortable in your unique style!
13 Jeans and Ankle Boot Outfits
Black Wide Leg Jeans and Ankle Boots
I love the combination of black wide-leg jeans with black ankle boots for a smart casual look in fall. The kitten heel on the boots dresses up the look, while the wide-leg jeans keep the outfit comfortable. When paired with a cozy sweater, this outfit is stylish and comfortable, perfect for everyday wear. This outfit is a go-to for me when I want an outfit that looks polished but feels comfortable.


Straight Cropped Leg Blue Jeans and Ankle Boots
When considering a pair of jeans to style with ankle boots, cropped straight-leg blue jeans are my favorite way to wear them. The cropped look highlights the boots perfect. When choosing a boot, my go-to choices are typically a kitten or block heel ankle boots for their style and comfort. However, this pair of straight leg jeans look works well with any type of ankle boot, from Chelsea boots to Western booties, allowing for plenty of versatility in personal style.

Cropped jeans are a favorite way to wear ankle boots, as they allow the boots to be fully showcased. This pairing works with various types of ankle boots, from flat styles to those with heels.


When wearing booties with a pair of straight leg jeans, don’t forget to consider the boot style. Whether you go for a pointed toe heeled boot, a flat sole, or even Chelsea boots, a straight leg jean is a good complement for most of these styles. However, remember that a heeled boot tends to dress up your outfit and a flat boot is better for a casual outfit idea.

Straight leg jeans are incredibly versatile. Pair them with ankle boots with a slightly higher shaft for a chic, effortless look. This combination works well for both casual and more dressed-up occasions.
Wide Leg Blue Jeans and Ankle Boots
Wearing wide-leg blue jeans with ankle boots can be a bit tricky, as it’s important to ensure the jeans don’t overwhelm the boots because of their wider leg opening. However, this combination works wonderfully when the jeans are the right length. I particularly love this look with the brown ankle boots, which not only complement the rest of my outfit but also look great against the blue. With wide leg jeans, its always a good idea to choose a pair of ankle boots with a heel, as it helps to balance the width of the jeans and adds a bit of elegance to the overall look.

Cuffed Wide Leg Blue Jeans and Ankle Boots

Wide leg jeans with a wider leg opening can be tricky to pair with ankle boots, but they can also be incredibly chic and on trend. For this look, try a cuffed jean style to avoid overwhelming the boots. Ankle booties that sit neatly under the hem create a stylish and contemporary silhouette. This especially looks good when you have a pointed toe silhouette to peak underneath the jeans.
Cargo Blue Jeans and Ankle Boots
Cargo blue jeans are on trend right now and pairing them with chic heeled ankle booties is an excellent way to dress them up. The combination of the casual cargo jeans with sophisticated boots creates a trendy and unique look, perfect for making a statement this fall. Wear this look anywhere from a brunch with friends to a business casual meeting.

White Split Hem Jeans and Ankle Boots
Split hem jeans are another pair of jeans that are on trend. And these pair wonderfully with ankle boots for a chic look. I personally love going for a monochrome white outfit with these jeans to create an elegant and cohesive vibe. Simply layer on a sweater and matching accessories to complete the look. It’s a chic, comfortable outfit that’s perfect for both casual outings and more sophisticated events. The split hem allows the boots to peek through, adding a subtle chic detail to the overall look.

Skinny Blue Jeans and Ankle Boots
Skinny blue jeans are great with ankle boots for a streamlined look, and can easily be dressed up or down. I like to wear skinny jeans with white kitten-heeled ankle boots for an elevated casual chic style, and they also work well with a blazer for a smart business casual look. This combination is simple yet effective for a variety of occasions this fall and winter.


When you wear skinny jeans, opt for ankle boots that snugly fit around the ankle or choose a boot with a higher shaft for a seamless transition. This look will help to flatter your overall outfit.
White Straight Leg Jeans and Ankle Boots
White straight-leg jeans paired with matching ankle boots create a stunning monochromatic look that I absolutely adore. This look is perfect for a chic work outfit or any business casual event during the fall or winter. Also, to adapt this outfit for colder weather, simply layer on a coat, enhancing both the warmth and style of the look. And if you’re loving the light colored boots look and are looking for more nude boots outfits be sure to check out my post here for more inspiration.

Be sure to check out my most recent posts for more classy style inspiration!
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Please feel free to email me at thegraydetails@gmail.com if you have any questions! I’m always happy to help with styling or picking out a specific outfit for an event! Have an amazing day!!
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