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How to Wear Ankle Boots with Jeans (+ 19 Outfit Ideas)

I think we can all agree that a great pair of ankle boots are one of those wardrobe essentials that won’t be going anywhere anytime soon. Ranging from sleek and modern to rugged and edgy, this boot style has long been used as a go-to shoe style for the cold weather months. But they also raise an age-old question: what pants should I pair them with?

Ankle boots may be endlessly versatile, but there are a few considerations to make when deciding which jeans to pair with them. Thankfully, today’s post is here to save the day!

We’ll be going over how to select the perfect pair of ankle boots for your wardrobe, how they pair with each style of jeans, and a few bonus tips on making the most of this classic style. We’ll even share some real life outfit ideas to give you some ideas on the best way how to wear ankle boots with jeans!

Let’s jump into my guide on how to wear ankle boots with jeans.

How to Wear Ankle Boots With Jeans

How to Wear Ankle Boots with Jeans

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The 3 Main Types of Ankle Boots

Booties come in all shapes, sizes, and colors, but generally, there are three main types you’ll come across: tall, medium, and low ankle boots. Depending on your own personal taste and wardrobe, you’ll want to make sure you pick the pair of boots that will grant you the most wearability.

Tall booties will usually hit a few inches above your ankle boots and are often slightly wider in calf width. This style is especially popular lately, giving a current and modern vibe to your style.

Medium heights are by far the most common style you’ll come across. These are probably what you first think of when you hear “ankle boots”. These usually hit about an inch or so above your ankle bone and generally are slightly more fitted to the calf.

ankle boots

Low ankle boots are a bit more uncommon. This style will generally hit right at or just below the ankle bone. This style is a great option for spring and looks great with leggings, rolled jeans, and even skirts.

Which Boots Work Best with Which Jeans?

This is a question that often plagues even the most seasoned fashionista. But thankfully, there’s an easy answer: it’s all about height.

This means taking the height of your boots and the crop of your jeans into account in order to create the most flattering look. Here is a breakdown on pairing your ankle boots with some of the most popular types of jeans.

Skinny Jeans

red ankle boots, skniny jeans and grey cardigan

Of course, the most popular jeans style out there is also one of the best styles to pair with ankle boots! A slim fit pair of jeans leaves little room for awkward bunching or unflattering looks. However there are still a few details to consider depending on the height of your boots.

The first option is the classic rolled leg. This involves cuffing the hem of your jeans to create a neat and streamlined look, and is great for adjusting your look to accommodate varying boot heights. It’s also incredibly flattering, drawing the eye to the smallest part of the leg.

The key to this style is to pay attention to the cuff. You’ll only want to roll your jeans once or twice to avoid making the cuff too wide and bulky on your leg. It’s also important to make sure you keep the cuff no more than 2-3 fingers high in width. This is the best option when wearing low and medium-height ankle boots.

ankle boots in fall

If your skinny jeans are more cropped a single cuff is the easiest way to get a chic look by showing just a sliver of skin. If they’re a bit longer you can do a single wide cuff to get the same effect. The type of cuff will depend a lot on the type of jeans and the inseam length.

The next option is to tuck your jeans into your boots, but you’ll want to be careful with this one. To avoid any awkward bunching, ensure that your skinny jeans are fitted at the ankle and that your boot’s calf width is wide enough to accommodate your jeans. As you may have guessed, taller ankle boots are the best choice for this method.

If you’re looking to make styling your ankle boots and skinny jeans even easier, consider a pair of raw-hem jeans. This style is often slightly cropped and will fall perfectly over most pairs of ankle boots. These are very on-trend at the moment and can be found just about everywhere. But you can also make your own pair if you’re feeling a bit crafty!

Wide Leg Jeans

ankle boots with jeans outfit

It’s safe to say that wide leg jeans or flare jeans can seem daunting when styling ankle boots. But not only are they easier to pair together than you might think, but booties often look incredibly classy and high fashion when paired with wide leg jeans.

color block sweater and flare jeans

Medium and high ankle boots work well for this style. This may seem unexpected, but these styles will perfectly complete the streamlined look without showing a sliver of skin of your ankle when walking.

Straight Leg Jeans

pink and red shacket and straight leg jeans outfit

We’re seeing more and more straight leg jeans in stores and on the streets, and thankfully, it’s just as easy to pair ankle boots with this style as skinny jeans! In fact, they may be even easier to style, since they don’t have to be tucked or rolled.

When wearing this style, it’s all about finding a pair of jeans with the perfect inseam. Full-length ankle jeans will usually fall seamlessly over the shaft of your boot, but you’ll want to pay closer attention with cropped styles.

cropped jeans and cardigan

While cropped straight leg jeans often end up working perfectly with ankle boots, you want to make sure there isn’t too much space between the top of your boot and the hem of your jeans. This can create an unflattering effect that looks awkward and cuts off the line of the leg.

For this reason, make sure to keep the gap between the boots and jeans less than an inch wide. Depending on the length of jeans, low, medium, and high ankle boots can all work well with this style.

Start with the Jeans

Of course, in addition to your ankle boots, your jeans are important in making the most of this outfit combo. Before jumping into buying your perfect pair of ankle boots, you’ll want to make sure you have the perfect pair of jeans.

Consider how your jeans will fit into your wardrobe. Do you tend to go for darker or lighter colors? Do you consider your style more trendy or more classic? Will you be wearing your jeans casually, or more dressed up? These are the types of questions you’ll want to ask yourself when making your selection.

cognac ankle boots

Additionally, fit and quality are everything! Especially if you find yourself living in jeans, you won’t regret taking the time (and money) to ensure you get the best pair possible.

Confused by inseam? Head to this post to learn everything you need to know about your jeans inseam and the impact it has on your outfits!

If you find that your jeans bunch around the ankles or are a bit loose around the legs, this can be fixed! Just visit a tailor in order to have them perfectly customized to your height and figure. It may seem like overkill, but having jeans that perfectly fit your body will make getting dressed and looking amazing much easier.

Consider Your Own Closet When Shopping

Trying to find the perfect pair of ankle boots can be overwhelming, to say the least. With a myriad of varying choices on today’s market, you’ll want to carefully consider a few details before purchasing, especially in regards to height and ankle width.

First, think about what type of jeans and pants are most abundant in your closet. Do you find yourself with more pairs of wide leg jeans, flare jeans or straight leg jeans?

Or are you more of a skinny jeans type of girl? Ankle boots are going to be one of the most versatile accessories in your closet, so you’ll want to maximize their potential wear time as much as possible.

flare jeans and shackets

Just like with jeans, you’ll also want to think about your personal style and the colors you find yourself wearing. Lovers of all things black can’t go wrong with a sleek pair of black ankle boots. Inversely, nude or tan booties always look great with a lighter color palette.

Lastly, consider the material. Most boots will be either smooth leather, faux leather, or suede. Smooth or faux leather options will often give you a more expensive and classic look, but suede is often more flexible and comfortable to wear. My go to pair of boots (as you’ll see below) are suede. I love them!

Ankle Boot and Jeans Outfit Ideas

Want to see some different ways to wear ankle booties and jeans for some inspiration? Here’s a simple style guide with some different outfit ideas for wearing booties with jeans. Some of these will work better for different time of year (fall vs winter, etc) but hopefully it gives you some ideas!

1. All Black

all black outfit

Sweater | Boots

One of the most simple yet classic outfits to wear is all black! But don’t wear all black from head to toe. Give it a pop of color in you bootie. I love the look of a sleep black sweater or black top paired with black jeans accented with tan or printed boots.

You could wear brown boots with gold jewelry like I did here. Or you can pair your black on black with a printed boot (think snake skin or leopard boots). The pop of color in your shoe will have you looking like quite the fashionista!

As a general rule, cropped pair of jeans look great with a tall boots (as opposed to the shorter ones) so your legs don’t look extra short).

2. Single Cuff with Blazer

Single Cuff with Blazer

Similar blazer | Similar button down

Casual Friday? Work in a place where jeans are ok? This look is for you. The single cuff of the jeans gives your legs a long, lean look. The button down top paired with a casual blazer keeps things professional while the embellished bootie adds a bit of flair!

Swap the button down for a graphic tee and your ready for cocktails after work!

3. Cardigan and White Tee

Cardigan and White Tee

Cardigan | Crewneck t-shirt | V-neck t-shirt | Jeans | Boots

Love neutrals? We’ve got you covered. Pull on some dark skinny jeans with a double cuff to them making sure you can see a bit of skin at your ankle.

Pair it with a white tee and long duster cardigan, gold jewelry and tan booties! You’re ready to be the girl everyone comes to for fashion advice!

Find style tips for this outfit here!

4. Black Skinny Jeans and Denim Jacket

Black Skinny Jeans and Denim Jacket

Jacket | Boots (similar)

Running errands but still want to look good? Here you go! These black skinny jeans paired with wedged boots makes my leg line look extremely long (news flash – I’m actually really short!). I cuffed them twice to make them the right length and not bunch up on top of the boots.

Knotting a white button down gives it a more casual look to it and a denim jacket is the perfect completer piece, giving you that fashionista vibe.

5. Wintery Layered Look

Wintery Layered Look

Boots (similar)

If you’re wearing ankle booties in the winter, chances are you’re going to want to layer up your look a bit! Having a solid neutral base – darker wash jeans, a longer black and white top and grey jacket is a great way to set the tone of your look.

Adding a scarf with a bit of a pop of color gives you that boho feel to it and a bit of life to an otherwise muted palate.

You’ll notice that these jeans needed just one tiny cuff to make the perfect length for my booties.

6. Maroon Pants

Maroon jeans and vest

Jeans (similar)

Need a look that doesn’t include a regular pair of denim? Try colored jeans! These maroon pants are the perfect way to welcome fall in a chic way. Keep the rest of your outfit in neutral tones keeps this look professional enough for the office yet fun enough for a quick dinner out with friends.

These pants are extra long so doing one long cuff followed by another cuff that doesn’t quite reach the top of the first cuff gives it a unique look without bunching or looking unkempt.

7. Jeans and Combat Boots

Jeans and Combat Boots

Jacket | Boots (similar)

Heading out to tromp in the snow but don’t want to wear winter boots? Pull on a pair of combat boots! These boots will keep you stable and (mostly!) warm when out in the wintery mix.

A pop of red in your jacket will keep you looking chic all winter long!

8. Colored Ankle Boots and Jeans

Colored Boots

Nothing says fashionista like a great pair of colored boots! Start with simple, neutral colors – a pair of skinny jeans in a dark wash and a white top and throw on a pair of studded colored boots!

Your boots will speak for themselves so keep your jewelry to a minimum and don’t try to overpower them. You’ll be the talk of the town (in a good way!) in this outfit!

9. Red Cardigan and Gold Accents

 Red Cardigan and Gold Accents

Can you mix brown and red? Heck yes! I love the look of brown and red together (this is just my personal preference – you can totally disagree!) and love the look of this outfit.

A knotted white tee gives you a solid base for some simple gold necklaces which pull in the gold bangles. The brown cut out of the boots give them a fun look and the red cardigan is a beautiful completer piece!

*Find 4 easy ways to tuck in a shirt here!

10. Black Jeans and Chambray Top

woman wearing black jeans, chambray top and cardigan over it with ankle boots

Chambray (similar) | Pants | Boots

One of the most classic outfits ever will be dark denim (I love a pair of black jeans!) and a chambray top. It always looks chic whether you knot your top or tuck it in!

Pair it with a some tan booties, add some bracelets and a chunky necklace and you’re good to go!

If it’s extra cold out, add a long sweater over the top! Chic, warm and perfect.

*Find more chambray shirt outfits here.

12. Stripe Top with Chambray

Stripe Top with Chambray

Chambray | Pants | Boots

A simple twist on your classic chambray top and dark denim is to add a stripe tshirt or graphic tee underneath! Keep your chambray shirt unbuttoned so your t-shirt peeks out for a fresh and new look.

13. Pops of Red

Pops of Red


If you love denim on denim, here’s a simple way to keep it looking stylish. Add a longer red top underneath to break up the denim on denim (aka the Canadian tuxedo look).

A wide cuff of the jeans helps draw your eyes down towards your cute booties and a red beanie on top keeps you looking young and fresh!

14. A Little Leopard Belt

A Little Leopard Belt

Similar Balenciaga Bag | Belt (similar)

If you loved the pop of color on the booties in the outfit above, here’s another fun look! Keep the majority of your outfit neutral, like before, with dark blue jeans, a dark t-shirt and long grey cardigan. But add a pop of fun with a leopard belt tied around your waist!

The belt helps give your waist some definition and the leopard adds a fun print to your look!

15. Mix Patterns

Mix Patterns

Wedge Boots

Need to branch out from neutral looks? Try mixing some patterns! When you mix patterns like this, one simple tip is to spread them out! Stripes on top paired with camouflage boots on the bottom gives them enough breathing room in between so they don’t overpower one another.

16. Black Jeans and Cashmere Sweater with Neutral Boots

Woman wearing quince jeans and quince cashmere sweater

Pants | Sweater | Boots

Solids are always a winning combination and will forever look classy. These wide leg cropped jeans look perfect with the neutral boots!

Pair it with a simple, soft cashmere sweater and you’re going to look master that quiet luxury look we’re all loving!

Find my full Quince review here!

17. Grey Jeans and Chelsea Boots


Jeans | Stripe Shirt | Jacket | Chelsea Boots

Yes, you can wear Chelsea bots with jeans, even grey ones! The simple black and white stripe shirt ties in the black boots and the denim jacket is perfect for cooler fall days.

*Check out other Chelsea boot outfits here!

18. Ankle Boots with Straight Leg Jeans

pink and red shacket and straight leg jeans outfit

Shop the outfit: Straight Leg Jeans | White T-shirt | Pink Shacket | Boots |

Straight leg jeans or mom jeans are some of my favorite jeans to wear with ankle boots! The shaft of these boots end just above the bottom of the jeans which help elongate my legs instead of shortening them.

The bright color of the shacket combined with the neturals of the rest of the look really make this outfit a statement!

19. Flare Jeans and Ankle Bots with Cropped Shacket

flare jeans and shackets

Shop the Look: Jeans | White T-shirt | Cropped Flannel Shacket

Flare jeans can be hard to style with ankle boots. The biggest trick here is to have a boot with a pointed toe so your feet don’t get lost under the fabric!

Throwing on a cropped shacket will help your legs look longer and a tucked in shirt will help define your waist.

And there you have it! Ankle boots are a timeless staple that won’t be going anywhere anytime soon, so don’t be afraid to invest in a great-high-quality pair. You’re sure to get your use out of this classic style for plenty of falls, winters, and even springs to come.

2 thoughts on “How to Wear Ankle Boots with Jeans (+ 19 Outfit Ideas)”

  1. I love your blog so much! You give so much practical advice that I can actually apply to my closet. I look forward to your emails and all the little rabbit holes I can go down with the links you have to other posts. Thank you!


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