January 24, 2025
How to Wear Ankle Boots with Jeans: 10 Perfect Pairings for Every Style
No matter what your style is, there’s one article of clothing every closet shares: jeans. They’re timeless, reliable and versatile enough for nearly every occasion. If you’re looking for a way to give your denim a little oomph, you can’t go wrong with ankle boots, a time-tested classic that you’ll reach for season after season.
One of the things we love about this shoe is that learning how to wear booties is easy! But making this classic combination look intentional takes creativity and planning. So, how do you wear ankle boots with jeans? The truth is that there’s no one-size-fits-all rule. Like everything in fashion, it’s about finding the right balance between cuts, lengths and proportions — and sprinkling in your personality to make it all your own.
The good news? With a few styling tips, you can take this combo to new heights and create looks that feel effortless and uniquely you. If you’re on a mission to learn how to wear jeans and ankle boots, we’ve got 10 stylish and fun ways to make the most out of these go-to pieces.
1. Black Ankle Boots With Printed Jeans
Black ankle boots with jeans never go out of style. And, for a little extra personality, pairing them with printed jeans is a surefire way to stand out. From something bold and eye-catching, like animal prints or bold florals, to subtle geometric patterns, the sleekness of black boots grounds the quirkiness of printed denim. It’s a combo that works well for casual outings, creative-casual office days or any time you want to elevate your look without overthinking it.
Styling Tip: Choose a fitted ankle boot that hugs your leg to let the print take center stage. If your jeans are cropped or have a tapered fit, leave a slight gap between the hem and the boots to break things up visually. Plus, consider keeping the top simple — think solid colors or subtle textures — to balance out the statement jeans.
2. Wedge Ankle Boots With High-Waisted Jeans
Booties and high-waisted jeans are equal parts stylish and comfortable. But how do you wear short boots with jeans that sit high on the waist? Again, it’s all about balance. Choose slightly higher booties, like wedges, to complement the leg-lengthening effect of high-waisted jeans. This will help create an elegant and flattering silhouette with laid-back retro vibes. Wear it for a trip to your local coffee shop or when you want an easy, chic look that feels effortless.
Styling Tip: To keep the look clean, wear high-waisted jeans with straight or skinny cuts. Tuck in a fitted or semi-fitted top to emphasize your waistline, or opt for a flowy blouse for a boho aesthetic. If you’re layering, choose a cropped jacket or one that cinches at the waist to highlight the leg-lengthening effect of this combo.
3. Suede Ankle Boots With Mom Jeans
Oh beloved mom jeans, the trend that gave us style and comfort. Their relaxed fit doesn’t mean they always have to be fully casual, though. If you want to elevate the look, go suede! There’s something about the texture of suede boots that works seamlessly with the looser fit of mom jeans. The soft material adds a touch of sophistication, while the jeans keep the outfit grounded and laid-back. This combination is great for everyday wear, from casual Fridays at the office to lunch with friends or picking the kids up from school.
Styling Tip: Try cuffing the hem of your jeans to show off the boots and create a more intentional look. Pair with a tucked-in graphic tee for a casual vibe or a cropped cardigan. Or, take the outfit from day to night with a structured coat that pulls everything together.
4. Heeled Ankle Boots With Boyfriend Jeans
Boyfriend jeans are one of those cuts that look great on every body type. But how do you wear jeans with ankle boots when you need to style a more relaxed fit? The secret here is creating contrast. When you wear heeled ankle boots instead of flat booties, the added height balances the loose, laid-back feel of boyfriend jeans. It’s a perfect pairing for when you want to look chic and modern — without looking like you spent hours planning your outfit.
Styling Tip: Cuff the hem of your boyfriend jeans to sit just above the boots, highlighting the heels and keeping the proportions balanced. Pair with a fitted or tucked-in top to define your silhouette, and finish the look with a blazer or longline coat to create more layers.
5. Chelsea Ankle Boots With Cropped Flare Jeans
Bring the flair with flare jeans! We love cropped flare jeans for their playful, vintage quality. But figuring out what shoes to pair with this one-of-a-kind cut can be tricky. Chelsea boots are a perfect match thanks to their fitted design that complements the flared hem. Together, they create a look that feels modern, easygoing and just the right amount of edgy.
Styling Tip: Choose Chelsea boots with a slightly higher shaft, so there’s not too much of a gap between the jeans and boots. We suggest keeping it simple on top — choose a tucked-in tee or fitted sweater with a cropped jacket, and you’ve got a relaxed outfit that still feels current and put together.
6. Metallic Ankle Boots With Black Jeans
Looking to spruce up your style? If you have a pair of metallic boots sitting in your closet or you’re thinking about adding some to your collection, you need to know how to wear jeans with ankle boots that literally shine. The easiest answer? Black jeans. They’re simple, classic and let your boots take centerstage. You can choose boots in whatever metallic color you want and black jeans will always pair perfectly.
Styling Tip: Go for black skinny or straight-leg jeans that hit just at the top of the boots for a cleaner look. Pair them with a tucked-in tee or a cozy sweater to keep the outfit casual but stylish. To finish it off, throw on a jacket — leather or denim works great — and keep accessories minimal so that your boots remain the star of the show.
7. Minimalist Ankle Boots With Bootcut Jeans
Bootcut jeans are timeless, and pairing them with minimalist ankle boots is a foolproof way to keep your look cool and modern. The simplicity of the boots balances the subtle flare of the jeans, creating a combination that feels chic and effortless. Plus, it’s a versatile match that works for casual days and more formal outings. You simply can’t go wrong with jeans designed for boots.
Styling Tip: We recommend choosing designs with a slim profile that fit neatly under the jeans. Keep the hem just grazing the top of the boots to create a longer line and add a fitted blouse or tucked-in shirt to highlight your shape.
8. Leather Ankle Boots With Skinny Jeans
Who doesn’t love the look and smell of leather? Dark leather ankle boots with jeans that hug your curves are a tried-and-true combination that always delivers. The snug fit of skinny jeans pairs perfectly with the structured look of leather boots, making this duo versatile enough for a casual daytime event, a romantic dinner date or an evening out with friends.
Styling Tip: Tuck your skinny jeans into the boots to keep your lines clean, or let ankle-length jeans sit just above the boots for a little breathing room. If you want to create a more dynamic look, create balance with an oversized sweater, flowy blouse or cropped jacket. Add a scarf or a simple necklace to give the outfit an extra layer of style.
9. Chunky Ankle Boots With Distressed Jeans
Chunky ankle boots are famously hard to style because their design can easily overwhelm an outfit. Distressed jeans (especially slightly looser or cropped ones) provide the perfect canvas for playing around with this iconic style. The casual-chic look balances out the heaviness of the boots, creating a fresh and modern vibe. Together, they make an outfit that’s edgy yet approachable, perfect for transitional seasons or days when you just want to switch things up.
Styling Tip: Go for slouchy straight-leg jeans or cropped jeans that sit just above the boots to keep the proportions balanced. Pair with a simple top, like a knit sweater or a tucked-in tee, and add a light jacket for a little extra texture.
10. Lace-Up Ankle Boots With Straight-Leg Jeans
It’s important to know how to wear ankle booties with jeans in the straight-leg cut, as the balance between the structured fit of the jeans and the shape of the boots can make or break the look. To get this look right, the trick is in the details. Lace-up ankle boots are a perfect match for straight-leg jeans thanks to their clean lines and streamlined silhouette, which seamlessly complements the tailored vibe of the denim. The chic silhouette of straight-leg jeans pairs effortlessly with the rugged vibe of lace-ups, helping you achieve a casual look that doesn’t skimp on personality.
Styling Tip: Tuck the hem of your jeans slightly into the boots or let them skim the top of the boots for a more relaxed vibe. Pair with a fitted turtleneck or a chunky sweater to create contrast and add dimension to your outfit. To complete the look, layer on a tailored blazer or a cropped leather jacket for an ensemble that’s equal parts refined and edgy.
The Do’s and Don’ts of Wearing Jeans With Ankle Boots
The outfit suggestions above are just that — suggestions. You don’t have to buy a whole new wardrobe just to make it work with your shoes. Before you hurry over to your closet to try out these combos, keep in mind these do’s and don’ts for how to style ankle boots with jeans:
Do’s
- Cuff or crop jeans to highlight the boots.
- Pair slim jeans with chunkier boots and looser jeans with more fitted boots.
- Match textures like suede boots with structured denim or leather boots with soft, worn-in jeans.
- Use higher-shaft boots with cropped or flared jeans to keep proportions balanced.
- Let bold boots shine by keeping the rest of the outfit simple.
- Play with layers like jackets or coats to tie the look together.
- Make sure hems graze the boots instead of bunching over them.
Don’ts
- Let jeans bunch awkwardly at the ankles.
- Completely cover boots with overly long jeans.
- Pair wide-leg jeans with bulky boots.
- Overcomplicate your look if the boots are already a statement.
- Ignore hem lengths. Different styles of jeans need different boots.
- Hide bold boots under jeans. Let them stand out.
- Wear overly tight boots that create awkward gaps with your jeans.
Wear TOMS. Wear Good.
Learning how to wear booties with jeans is all about you and your unique style. At TOMS, we’re passionate about helping people find high-quality products that look as good as they feel. That’s why we create boots and booties that tick all the boxes, allowing you to step from season to season in comfort and style.
Plus, with every pair you buy, you help make a difference in people’s lives through programs that create real, meaningful change. Learn more about our impact.
Shop our women’s collection to find the perfect pair today!