How To Wear Ankle Boots With Jeans (2023 Style Guide)

Ankle boots and jeans are similar in several ways, such as they are always in style, there are several styles and colors, they are versatile, easy to wear, and there’s always something for everybody. Due to these similarities, they make a great combination. However, it’s possible to go wrong when styling these two fashion staples. 

In this guide, I will show you how to wear ankle boots with jeans. I will also give you several outfit combinations you can try and answer your frequently asked questions about ankle boots and how to incorporate them into your style. 

Types of Jeans to Wear With Ankle Boots

wearing ankle boots

Skinny Jeans

One of the ways you can wear ankle boots is with a pair of skinny jeans. This is one type of jeans you can’t go wrong with while wearing ankle boots. However, since the bottom of skinny jeans differs, there are different ways they work with ankle boots. 

The first way you can wear your ankle boots with skinny jeans is by tucking your jeans into the boots. Since they are a slim fit, they’ll easily fit into your ankle boots but be careful while doing this. 

Make sure your skinny jeans are long enough to fit into your boots without stretching them. Ensure your boots can fit your jeans without appearing bulky or awkward and that your ankle boots rest above your ankles and not below them. Finally, check if the hem of the jeans slips out while you walk. If it does, don’t use this style. 

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The next style is raw-hem skinny jeans. This type of jeans is usually roughly cropped at the ankle. Ankle boots that go past your ankle or stop at your ankles are great for this style of jeans. 

Alternatively, the bottom of your skinny jeans can be cuffed for a different style you can wear your ankle boots with. If you wish to cuff the leg of your jeans yourself, ensure you cuff your jeans once or twice. Only roll the hem once if it reveals the smallest part of your leg. 

Make sure the cuffed part of your jeans is about a finger away from your legs. If not, roll the bottom of your jeans twice. Note that if the hem of your skinny jeans stops a few inches above your ankle, there’s no need to cuff them because it already shows skin. 

Bootcut Jeans 

Bootcut jeans are another easy way to style your ankle boots. These jeans have wider bottoms, which work well with booties.

Since it’s easy for ankle boots to end up being swallowed by the wide bottom of bootcut jeans, it’s best if you wear a style of ankle boot that sticks out at the bottom. For this, I recommend you wear an almond or pointed toe which will not get covered up with wider bottom jeans. 

Wear ankle boots with heels to stretch your legs and reveal more depth to the style. If your ankle boots and bootcut jeans aren’t mixing well, it’s probably because your booties are too flat. An inch or two of heels can go a long way in creating that flattering look you desire. 

Straight-Leg Jeans

Straight-leg jeans are as simple looking as the name suggests and go straight down from the waist to the hem. They are easy to style and can be baggy (boyfriend jeans) or slim fit but not skinny. Styling straight-leg jeans with ankle boots is quite easy as long as you keep these points in mind. 

First, pair your ankle boots with straight-leg jeans that stop right at the top of your booties. It shouldn’t reveal skin or cover your ankle boots. If you have ankle boots that stop right before your ankle, you should pair them with loose jeans that don’t have a wide bottom. Also, ensure there’s only a sliver of skin showing. 

Baggy Jeans 

Baggy jeans are great with ankle boots. They are easy to pair, but there’s a catch. You should always let the hem of the jeans fall over the ankle boots. This way of wearing ankle boots works with any type, from Chelsea boots to lug-sole to western ankle boots. 

If the hem of your baggy jeans is too long and there’s a high chance of you tripping on them, you can cuff it once. Cuff your baggy jeans in a way that doesn’t reveal skin. 

Simple Jeans and Ankle Boots Outfits

man wearing boots

If you’re looking for ankle boots and jeans style inspiration, I have the perfect outfit combos for you to try. These are simple and require basic clothing you probably already have in your closet.

1. Blue Straight-Leg Jeans + Heeled Ankle Boots + Jacket 

This is one of my favorite ways to style ankle boots. Get a pair of blue straight-leg jeans that are not too loose. You can wear a turtleneck or a cropped hoodie or top, depending on the weather, then get a heeled ankle boot. 

For this look, your jeans should sit over your boots and not reveal your skin. Also, avoid cuffing your jeans with this style. Get your favorite jacket, whether it’s a leather jacket, a trench coat, or a denim jacket. 

2. Wide-Leg Jeans + Shirt + Heeled Ankle Boots 

This outfit is great for one of those days when you have nothing to wear but still want to look stylish. Grab a pair of wide-leg jeans, your favorite shirt, and heeled ankle boots. Ensure you wear a pointed or square-toe ankle boot so it sticks out from the wide-leg jeans. Also, tuck your shirt into your jeans. 

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3. Cuffed Straight Jeans + Lug Sole Ankle Boots + Sweater Dress

If you’re looking for a cozy outfit, wearing a pair of jeans and a sweater dress with your ankle boots is a great combination. Get a pair of cuffed straight jeans, but ensure the cuff is not too bulky or wide. 

Wear a sweater dress on top, but ensure it’s not so long that it hangs awkwardly over your body. You can also tuck the front part of the sweater into your jeans. Next, wear a lug sole ankle boot that sits directly under your jeans. 

4. Ankle Boots + All Black 

If you’re stuck on how to wear ankle boots with jeans, this combination is super easy to pull off. Grab a pair of black jeans and any black top of your choice. Then pair it with any ankle boot of your choice. 

Instead of wearing black ankle boots, try wearing some other color. Not only does this complement your outfit well, but it also makes your boots pop. You can wear brown or red ankle boots or if you have one with an animal print, this is a great way to style them. 

5. Raw-Hem Jeans + Chunky Ankle Boots 

If you want an edgy look that’s easy to put together with your ankle boots, try out this combination. Grab a pair of raw-hem jeans and pair it with chunky ankle boots with big buckles. 

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6. Straight Leg Jeans + Jacket + Red Ankle Boots 

If you want to play with colors but still look classy and elegant, this combination will blow your mind with how easy it is to achieve. First, grab a pair of white straight-leg jeans then tuck in a black top and a black jacket. You can then wear a pair of red ankle boots. 

Using this same concept, you can wear a pair of blue straight-leg/ mom jeans, a peach top, and a long brown plaid long coat. You can wear peach-colored ankle boots with them. 

7. Western Ankle Boots + Blue Jeans + White Top

Most people claim Western ankle boots are the hardest to style but it’s quite the opposite. They are stylish on their own so you don’t need too much to spice it up. A simple pair of jeans and a white top is a perfect combination for this kind of boot. You can throw a leather or denim jacket into the mix. 

8. Jean Dungarees + Ankle Boots 

This is another casual way of wearing ankle boots with jeans. You can wear long or cropped dungarees with any top of your choice. This type of jeans works with almost any booties. You can wear stiletto booties with long dungarees cuffed at the hem. 

Or you can wear blocked-heel ankle boots. Lace-up or flat ankle boots are also great for wearing jeans dungarees. You can also spice up your outfit a bit more with a long leather jacket or a long coat. 

9. Jean Shorts + Booties

On a sunny day, you can wear jean shorts and booties for a lunch date with friends. It’s incredibly easy to style with flat ankle boots, cowboy boots, or pointed-toe booties with an inch or two heels. You can also wear a hat while rocking this outfit or opt for a belt. 

Why not try to mirror Taylor Swift’s style by wearing a pair of blue jean shorts, a shirt, and brown booties? To make this outfit even more interesting, add one of your favorite jackets into the mix. I strongly suggest you wear white jean shorts while trying out this combination. 

How To Spice Up Your Ankle Boots Outfit 

woman wearing boots

So you’ve put together the whole outfit and you still feel like something’s missing? Not to worry, below I have listed a few simple ways you can further spice up your ankle boots outfit. 

Try these out to see the difference between before and after.

1. Jewelry

Wearing jewelry is important when creating any outfit. Those pairs of earrings that make your eyes pop or match your coat might be what changes your outfit from good to great. 

There are different ways to accessorize your ankle boot outfit with jewelry. If you’re wearing a classy outfit, a pair of round earrings are a great accessory. Also, wearing different kinds of rings is great. Other accessories you can try are bracelets, wristwatches, or necklaces. If you’re having doubts about what accessory to wear, stick to rings and earrings. 

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2. Jackets 

Ankle boots and jackets are one of the greatest outfit combinations. It’s almost impossible to go wrong with it. If you feel like your outfit is too simple or nothing is going on, you can put on your favorite jacket to match your outfit. My go-to jackets are a leather or denim jacket, a long coat, or a trench coat. 

3. Bags 

Bags are a great way to spice up your outfit. Also, they can help you appear bold and confident. There are not many restrictions with pairing bags with your ankle boots. However, you have to ensure the bag matches the outfit and occasion. Asides from boosting your style, bags are also necessary to keep your items safe.

4. Belts 

Belts are great for styling mom jeans. They can be simple yet they go a long way in elevating your outfit. Many people think belts are mostly used to hold a pair of jeans that doesn’t fit tight on the waist. While this is correct, it’s not its only use. You can also put on a belt as an accessory for your outfit. Simple yet cute. 

5. Sunglasses 

Stuck on what way to spice up your ankle boot outfit? Grab your favorite pair of shades and go about your day. 

Types of Ankle Boots

There are so many types of ankle boots and it’s almost impossible to name them all. However, these types are the easiest to style and they’re always in trend:

1. Block Heel Ankle Boots 

Block-heel ankle boots are comfortable, stylish, and classy. They are pairable with almost any kind of jeans which makes them a favorite for many people. This type of ankle boot can either have a square or pointy toe. 

2. Cowboy Ankle Boots 

Cowboy ankle boots are always in style and as we’ve said before, they are easy to style and go with almost everything in your closet. There are several styles of cowboy ankle boots including animal print, leather, or velvet. 

3. Chelsea Ankle Boots 

These are comfy and stylish. If you want a casual laid back outfit, pair these Chelsea ankle boots with your favorite jeans. They are perfect for any weather and match several fashion trends. 

4. Flat Ankle Boots

These are one of my personal favorites. They are stylish, chic, and versatile. If you’re an older individual that loves to rock boots, you should own a pair of flat-ankle boots. They’re incredibly easy to style and trendy – this type of boot is a must-have.

5. Stiletto Booties 

Stiletto booties are perfect for any occasion. It’s not just with jeans you can style them with. So owning a pair gives you something to wear with other outfits in your closet. They are one of the most popular types of ankle boots because there are many styles and colors to choose from. 

6. Lace Up Booties 

The origin of lace-up booties goes back hundreds of years and till this present time, they are still trendy. They are easy to style with straight jeans, skinny jeans, or cuffed jeans. 

7. Knitted Ankle Boots

Need a pair of booties for the winter? Get knitted ankle boots. These boots have a knitted design that is cozy and stylish. They are comfortable, warm, and soft. They can have a pointed or square-toe design. Also, some have block heels while others have stilettos. 

Tips On How To Wear Ankle Boots With Jeans

1. Stick To Your Style 

Sticking to your personal style will help you when styling ankle boots with jeans. While it’s good to wear something different from your usual, if you’re new to styling ankle boots with jeans, you should probably stick to your preferred style. 

So, if you typically don’t wear flat booties, there’s no need to get one. Wearing ankle boots with jeans according to style allows you to be intuitive about what feels right and what doesn’t. 

2. Comfort

What makes an outfit beautiful is how confidently you wear it. You cannot be confident in an outfit that makes you uncomfortable. This is why I advise you to wear what makes you feel good about yourself.

3. Keep It Simple

Simplicity plays a key role in wearing ankle boots with jeans. You don’t need to go over the top with colors and prints. Jeans and booties can stand out on their own so keeping the rest of your outfit simple is essential. 

Frequently Asked Questions

How can I maintain my ankle boot? 

Cleaning your ankle boots regularly is one way you can maintain them. Proper cleaning is important in determining how long they last. The first step is to be aware of the material your boots are made of –  velvet, suede, leather, etc. The cleaning method for suede boots is different from leather.

After confirming the material of your boots you should clean them accordingly. For example, you can use warm and slightly soapy water to clean leather boots. However, this will not work for suede boots which require a suede brush and suede shampoo to remove tough stains. 

Other tips for maintaining your boots include: 

  • Don’t put them in a washing machine unless instructions tell you to do so 
  • Always air-dry your ankle boots 
  • Clean them after every use 
  • Don’t neglect the insides of your boots
  • Store them in a dry area

Can I wear ankle boots in the winter?

Yes, you can wear ankle boots in the winter. One of the best ways you can wear your ankle boots during the winter is with jeans. Ankle boots are perfect for any season as long as you style them right. Ensure you wear comfortable booties during the winter. 

Can I wear socks with ankle boots?

Yes, you can wear socks with ankle boots. There are three easy ways you can do this. You can style your booties with thick slouchy socks that rest mid-calf. This casual style works great with dresses and skirts which show off the legs. 

Another way is to wear a pair of cuffed jeans, ankle boots, and socks that stop a few inches above the boots. 

Lastly, you can wear skinny jeans, ankle boots, and socks which cover your jeans. This is a pretty style but be careful not to pull your socks up. It should stop a few inches before your calf. 


Ankle boots are trendy, stylish, and comfortable. I advise every woman to own at least one pair because of how easy to style they are. Hopefully, this article has served as a useful guide to help you know how to wear ankle boots with jeans.

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