How to Wear Ankle Boots With Jeans: Outfit Ideas + 6 Styling Tips

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Every woman has the same pair of shoes in her closet. No, it’s not white sneakers. It’s not even a pair of nude stilettos.

The shoes you’re guaranteed to have in your closet are ankle boots. These boots have stood the test of time and are a girl’s best friend.

Heading to the office? Put on jeans and ankle boots. Hitting the town with your friends? Put on ankle boots with jeans.

This classic combination works for any occasion. When you master the art of how to wear ankle boots with jeans, you’ll always have something to wear.

Alicia Vikander, Nicky Hilton, Anne Hathaway, Katie Holmes, and Olivia Palermo show how to wear jeans with ankle bootsAlicia Vikander, Nicky Hilton, Anne Hathaway, Katie Holmes, and Olivia Palermo show how to wear jeans with ankle boots (Credit: Aurore Marechal / ABACA / ROger Wong / Janet Mayer / Startraksphoto / Jose Perez / INSTARimages)

These boots are the perfect investment in your closet as they work for almost any season. Come rain or shine, you can grab these shoes out of your closet.

We’re sharing our ultimate guide on how to wear ankle boots with jeans. You’ll find out everything you need to know about the different types of ankle boots, which jeans to style them with, and the ultimate do’s and don’ts.

The 3 Different Types of Ankle Boots

Like all good things in life, ankle boots come in different shapes and styles. A trip to your favorite department store will show you just how many styles you can choose from. The easiest way to think about ankle boots is to divide them by height: low, medium, and tall.

Not everyone will love all three. It can often take a little trial and error to find the right style for you. Start by considering your height and the type of jeans that you usually wear.

If your legs are slimmer, you can usually choose from any three heights. Tall boots are ideal for those with longer legs, while a medium ankle boot is the most versatile of them all.

1. Tall ankle boots

These ankle boots are wider in the calf and give you enough space to tuck the jeans inside your boots. While they’re shorter than thigh-high boots, this style is the perfect choice for milder climates.

Shorter than thigh-high boots, tall ankle boots are wider in the calf area, allowing you to tuck your jeans into the boots easilyShorter than thigh-high boots, tall ankle boots are wider in the calf area, allowing you to tuck your jeans into the boots easily (Credit: Andrey Arkusha / Shutterstock)

They make a statement without being too overpowering. A tall ankle boot will typically come with a block heel, adding an elevated feel to your outfit.

If you want ankle boots that you can wear through winter, look out for a taller style.

2. Medium ankle boots

If you’re splurging on one style, let it be medium ankle boots. This height is the perfect in-between option, stopping just above your ankle.

They’re more fitted than taller ankle boots, helping to give the illusion of slimmer legs, without causing your denim to bunch up.

The most popular ankle boot type, medium ankle boots stop just right above the ankles and are usually fitted, giving an illusion of slimmer legsThe most popular ankle boot type, medium ankle boots stop just right above the ankles and are usually fitted, giving an illusion of slimmer legs (Credit: Voyagerix / Shutterstock)

What we love about medium ankle boots is that they’re the most versatile. They sit in a sweet spot right between tall and low ankle boots, giving you the best of both worlds.

You can swap out sneakers or stilettos for a pair of medium ankle boots.

3. Low ankle boots

The style you’ll come across least is low ankle boots. These boots are ideal for those who are upgrading from sneakers to ankle boots and want to try something new.

You can style ankle boots with almost any kind of jeans. You can also experiment with styling these boots with leggings or dresses.

Low ankle boots are the perfect alternative to sneakers and can also be worn with dresses, jeans, or leggingsLow ankle boots are the perfect alternative to sneakers and can also be worn with dresses, jeans, or leggings (Credit: AmbientShoot / Shutterstock)

If you want to wear ankle boots during the spring and summer, the low ankle style is one you want to invest in.

Choose the Right Heel Height

The other thing you want to consider when shopping for ankle boots is the heel. While some ankle boots will be flat, others have a skyscraper heel. You want to choose the functionality of your shoes and when you typically wear your jeans.

If they’re your go-to for a night out, you might want to invest in ankle boots with a thin heel. If jeans are your everyday style, you’ll want a more versatile block heel.

1. Flat ankle boots

Most flat ankle boots fall into the ‘Chelsea boot’ category. They’re a classic style for pairing with jeans and are a more elevated alternative to sneakers.

These ankle boots work best with straight-leg or skinny jeans.

1. Tila March Chelsea ankle boots; 2. Dr. Martens Church leather Monkey boots; 3. Cole Haan Harlyn Suede ankle boots; Kork-Ease Ryder ankle boot1. Tila March Chelsea ankle boots, $338 at Farfetch; 2. Dr. Martens Church leather Monkey boots, $170 at Zappos; 3. Cole Haan Harlyn Suede ankle boots, $185 at Saks Fifth Avenue; Kork-Ease Ryder ankle boot, $189.95-$194.95 at Nordstrom

Most flat ankle boots will have a shorter shaft, meaning you want to cuff your jeans or tuck them into the boots for a seamless look.

2. High block heels

Block heels give you extra height without compromising on comfort. If you want an outfit of jeans and ankle boots that you can wear anywhere, you need a high block heel.

Whether you’re at the office or grabbing cocktails with your friends, this outfit will ensure you’re on the best guest list.

1. Lauren Ralph Lauren chain horsebit ankle boots; 2. MICHAEL Michael Kors Porter suede boots; 3. A.W.A.K.E Ariana boots; 4. Sam Edelman Anika boots1. Lauren Ralph Lauren chain horsebit ankle boots, $192 at Farfetch; 2. MICHAEL Michael Kors Porter suede boots, $195 at Saks Fifth Avenue; 3. A.W.A.K.E Ariana boots, $620 at Shopbop; 4. Sam Edelman Anika boots, $170 at Shopbop

A higher block heel is usually found on tall ankle boots and will help to elongate your silhouette to create the illusion of a slimmer silhouette.

If you can only invest in one pair of ankle boots to wear with jeans, we recommend this heel type.

3. Thin stilettos

Ankle boots are a staple for a night on the town. A thin stiletto instantly adds a seductive feel to any ankle boots. What we love about this heel type is that you can find it on almost any style of ankle boots.

1. Stuart Weitzman Stuart 100 ankle boots; 2. Schutz Ashlee slouch high-heel boots; 3. Veronica Beard Lisa Prem Lea booties; 4. BCBGeneration Haxah ankle bootie1. Stuart Weitzman Stuart 100 ankle boots, $595 at Nordstrom; 2. Schutz Ashlee slouch high-heel boots, $178 at Saks Fifth Avenue; 3. Veronica Beard Lisa Prem Lea booties, $495 at Shopbop; 4. BCBGeneration Haxah ankle bootie, $168.95 at Nordstrom

A thin stiletto ankle boot will work with any style of jeans, whether you’re wearing skinny jeans or a wide-leg style.

The height of the stiletto means that your boots will pop out under the wide-leg jeans or slim your legs when wearing skinny jeans.

4. Short block heel

A short block heel is a perfect combination to wear with straight-leg jeans. This ankle boot style sits between a flat ankle boot and a high block heel.

They give you a little extra height without having a thin heel, making them comfortable enough to wear all day long.

1. MICHAEL Michael Kors knitted-panel ankle boots; 2. Kate Spade New York Delina suede ankle boots; 3. Rag & Bone Rover booties; 4. Carvela Secil ankle boots1. MICHAEL Michael Kors knitted-panel ankle boots, $320 at Farfetch; 2. Kate Spade New York Delina suede ankle boots, $248 at Saks Fifth Avenue; 3. Rag & Bone Rover booties, $395 at Shopbop; 4. Carvela Secil ankle boots, $205 at Farfetch

You can style your jeans with a blazer and button-up shirt for a chic workwear look. These ankle boots are a perfect choice for a capsule closet that’s built around classic jeans.

What Jeans to Wear With Ankle Boots

Figuring out how to wear jeans with ankle boots is easier than you think. There’s one golden rule to follow. It’s all about height. Not just your height, but the height of your ankle boots and the crop style of your jeans.

Before you start shopping for ankle boots, you want to make sure you have the right jeans in your closet. While we love jeans, they can be some of the most problematic clothes to shop for.

They’re not a ‘one size fits all’ style. It’ll take a little trial and error to find your signature jeans to wear with ankle boots.

To help you with your shopping, there are a few denim styles that you should focus on. These jeans are the ones that will look effortlessly chic with almost any style of ankle boots.

1. Cropped jeans

One of the easiest jeans styles to wear with ankle boots is cropped jeans. You’ll get all the comfort of wearing your favorite jeans while showing off your new ankle boots in the process.

1. R13 Boy Straight Mid-Rise Distressed Stretch Crop Jeans; 2. Re/Done 90s cropped straight-leg jeans; 3. B Sides Lasso wide-leg cropped jeans1. R13 Boy Straight Mid-Rise Distressed Stretch Crop Jeans, $495 at Saks Fifth Avenue; 2. Re/Done 90s cropped straight-leg jeans, $325 at Matches Fashion; 3. B Sides Lasso wide-leg cropped jeans, $416 at Matches Fashion

The trick with this style is to find cropped jeans that end just before your ankle boots. You want to show off as much of your boots as possible.

2. Skinny jeans

Are skinny jeans canceled? We don’t think so. While the Gen Z of TikTok may have outlawed skinny jeans, we think they’re a classic that every woman should own.

Not only do skinny jeans show off your curves, but they’re also the perfect choice for ankle boots.

What makes this style so versatile is that you can easily tuck them into your boots for a seamless look. Styling ankle boots with skinny jeans will give the illusion of a few extra inches of height. What’s not to love about that?

1. Levi's High Rise Skinny Jeans; 2. Frame Le High high-rise skinny-leg jeans; 3. Paige Margot cropped skinny jeans; 4. Frame Le High Skinny Jeans, $210 at Saks Fifth Avenue1. Levi’s High Rise Skinny Jeans, $89.50 at Shopbop; 2. Frame Le High high-rise skinny-leg jeans, $193 at Matches Fashion; 3. Paige Margot cropped skinny jeans, $275 at Farfetch; 4. Frame Le High Skinny Jeans, $210 at Saks Fifth Avenue

If you’re cuffing your skinny jeans, make sure to keep the cuff no more than three fingers in height.

When you’re tucking your jeans into the ankle boots, you want to make sure the denim is fitted at your ankles to avoid them bunching inside your boots.

Taller ankle boots are a classic choice for wearing with skinny jeans but don’t be afraid to experiment with your shoe choice.

3. Straight leg jeans

Sometimes, jeans work so well with ankle boots that you don’t have to worry about how to style them. Straight-leg jeans tick all the boxes.

If you’re wearing low-rise ankle boots, you don’t have to do anything with your denim jeans. You can flash a little skin around your ankles to elongate your legs.

1. Levi's Ribcage straight ankle jeans; 2. B Sides Louis straight-leg jeans; 3. Le Jean Relaxed straight jeans1. Levi’s Ribcage straight ankle jeans, $108 at Saks Fifth Avenue; 2. B Sides Louis straight-leg jeans, $242 at Matches Fashion; 3. Le Jean Relaxed straight jeans, $258 at Shopbop

The trick with this styling look is to choose the right inseam for your straight-leg jeans. Shop around for a full-length style that flatters your body type and height.

Investing in the right jeans means that you can wear them with almost any style of ankle boots.

4. Wide leg jeans

If you’re not a fan of skinny jeans, chances are you’re living it up with wide-leg jeans. This silhouette is one of the most popular right now.

It’s easy to assume that the oversized shape means they’re not a good match for ankle boots. While they’re not the easiest to style, this combination can be one of the most sophisticated options.

1. DL1961 Hepburn High Rise Wide Leg Jeans; 2. Victoria Beckham Alina Wide-Leg Jeans; 3. Wrangler Heritage World Wide High Rise Wide Leg Jeans; 4. Frame Le Baggy wide-leg jeans1. DL1961 Hepburn High Rise Wide Leg Jeans, $199 at Shopbop; 2. Victoria Beckham Alina Wide-Leg Jeans, $490 at Saks Fifth Avenue; 3. Wrangler Heritage World Wide High Rise Wide Leg Jeans, $98 at Shopbop; 4. Frame Le Baggy wide-leg jeans, $305 at Farfetch

One of our favorite outfits is wide-leg jeans with high ankle boots. It’s a classic workwear look that you can elevate with a silk blouse or dress down with an oversized jumper.

The 6 Best Tips for Wearing Ankle Boots and Jeans

Are you not sure where to start with styling jeans and ankle boots? We’re sharing our ultimate tips in this section of our styling guide.

This list of ‘dos and don’ts’ are the golden rules of what to think about when putting together an outfit with jeans and ankle boots.

1. Cropped pants CAN shorten the body

Cropped jeans should always end before the top of your ankle boots. If they end too high up, it could shorten the length of your legs and make you appear plumper.

Depending on your height, you may find it easier to shop for ankle boots with a taller shaft instead of focusing on the jeans.

Cropped jeans should end just right above the ankle boots to create a flattering lookCropped jeans should end just right above the ankle boots to create a flattering look

2. How to wear ankle boots with skinny jeans

When you’re wearing ankle boots with skinny jeans, you want to avoid the denim bunching up over your boots.

It’s best to tuck the skinny jeans into your boots unless they are very short, in which case the denim will usually end up just above your ankle boots.

It's best to tuck your skinny jeans into your ankle boots to avoid the denim bunching up over your bootsIt’s best to tuck your skinny jeans into your ankle boots to avoid the denim bunching up over your boots

3. How to cuff jeans with ankle boots

Is your denim just not looking right? One of the quickest ways to switch up your look is to cuff your denim.

Cuffing your denim lets you show off your ankle boots and creates a contrast between the denim that elongates your legs.

Another benefit of cuffing your jeans is that it makes a more seamless look that is universally flattering for all body types and heights.

Switch up your look and show off your ankle boots by cuffing your denim jeansSwitch up your look and show off your ankle boots by cuffing your denim jeans

4. First pick the jeans you want to wear

When you’re putting together your outfit, start with the jeans. While some of us love building an outfit around our shoes, starting with your jeans means that you can narrow down which shoes to wear.

5. Choose versatile ankle boots that are easy to style

If you’re shopping for new ankle boots, don’t forget to consider your personal style and what you already have in your closet.

You want to choose boots in a versatile color that you can picture yourself incorporating into at least four or five outfits.

Don’t forget to consider the type of denim wash you typically wear, along with when you wear jeans. If you’re someone who wears jeans for a night out clubbing, you’ll want different ankle boots than someone who wears jeans as their signature day-to-day look.

6. Consider the season

Ankle boots aren’t just for autumn and winter. If you want to wear these shoes in spring and summer, shop around for a lighter color or a bold print. Textured ankle boots, such as snakeskin, work all year round.

Bold prints and textured ankle booties work all year roundBold prints and textured ankle booties work all year round

Whether you’re building a capsule closet or investing in your wardrobe, you need at least one pair of ankle boots. No outfit has your back more than jeans and ankle boots.

You can style with almost anything in your closet, taking you seamlessly from day to night. You can splurge on designer ankle boots or keep them affordable with a budget-friendly style.

Whichever style you choose, don’t forget to try out our tips and tricks on how to wear ankle boots with jeans. You’ll never want to wear anything other than jeans and ankle boots!

What are your tips for wearing ankle boots with jeans?

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