How to Wear Ankle Boots with Jeans

Every trendsetter has their comfort spot. For some, it’s a holey t-shirt, a pair of beat-up sneaks, or a cozy cable knit sweater. Others refer to complete outfits, given that styling coordination takes a great amount of effort in the morning. 

Ankle boots with jeans are considered a common go-to for many casual dressers. Stylish yet practical, it’s regarded as a basic fashion statement that’s relatively free of bells and whistles. If anything, it’s a level-up from the usual sweatpants combo.

Despite its versatility, ankle boots with jeans have been done to death. It requires a bit of an upgrade, especially for fashionistas who love to mish-mash various aesthetics. 

Obviously, there are different takes on this classic OOTD. Chelseas can be easily swapped for Demonias for an edgier look. On the other hand, high-waisted Levis can be switched for low-cut True Religion jeans as a homage to Y2K. The options are limitless. 

With that in mind, you’re probably wondering how to wear ankle boots with jeans.

Consider us your styling fairy godmothers, as we’ll share some trendy outfit ideas, fashion advice, and some shopping recommendations. Hopefully, by the end of this article, you’ll understand:

  • How to wear ankle boots with straight leg jeans 
  • How to wear jeans with ankle boots 
  • Classic boots and jeans varieties 
  • Ugly ankle boots with jeans outfit ideas to avoid 

What Is An Ankle Boot? 

With a short silhouette, ankle boots are the cropped version of thigh-highs and knee-highs. There are hundreds of designs to choose from, such as the coveted combat or the classic Chelsea. 

Lace-ups, the thickness of the tongue, the presence of elastic webbing, and other features will depend on the style of the shoe. It’s worth noting that there are usually two types of ankle boots on the market, that being a flat-footed design or the iconic heel. 

History Of Ankle Boots

Our obsession with boots is a prehistoric love affair. More specifically, 12,000 to 15,000 BCE, where cave paintings depicted people wearing animal skin shoes.

Future civilizations came to adopt the early wellington boot that was soon synonymous with different disciplines, social statuses, and classes. For instance, boots were adorned with dripping jewels to signify the Roman elite. 

The ankle cut first emerged in the fifteenth century but only rose to popularity during the eighteenth and nineteenth periods. 

Constructed out of silk and satin, the Adelaide heel was probably the first shoe that was meant to be fashionable rather than functional. Of course, they were also worn by the working class, but that didn’t stop the late Queen Victoria from sporting them. 

When To Wear Ankle Boots With Jeans

Before we discuss how to wear ankle boots with jeans, we thought it best to address the ‘whens’ first. 

Considered the main go-to for many casual dressers, this common combo is usually worn for everyday use.

Think of city-bound shopping, second dates, fast food runs, and laidback hangouts. Consequently, jeans and boots can never be worn formally. Trust me, you do not want to be the center of gossip at your friend’s wedding. 

In terms of seasons, ankle boots with jeans are best worn during early spring, fall, and winter. We don’t recommend donning this outfit in summer, as its full-coverage silhouette is bound to produce sweats and chafing. 

How To Wear Ankle Boots With Jeans

Despite their surface-level specificity, ankle boots with jeans are open to hundreds of outfit possibilities. Do you opt for bell-bottoms or skinnies?

For shoes, should you wear Chelseas or Naked Wolfe? Ultimately, it depends on what you own currently in your closet, but that shouldn’t discourage you from keeping a Pinterest board of things to shop (or thrift) for. 

For those stuck in a styling kerfuffle, we’ll show you how to wear ankle boots with jeans using 10 outfits. Let’s get started! 

10 Outfit Ideas For Ankle Boots With Jeans

If Emily Cooper truly wanted to blend in with the Parisian fashion scene, she should ditch her love for maximalism and proclaim a newfound obsession for ‘minimalism romance.’ 

Sweet, innocent, and refreshingly casual, this OOTD features a pair of mid-wash denim, a pearly white sweater, shiny ankle boots, and a matching crossbody bag.

It’s the kind of outfit that screams ‘cappuccinos in cafes’ and ‘strolls by the Champs Elysees.’ This, ladies and gents, is how to wear ankle boots with jeans without resorting to a grunge-based edge. 

Black is usually the safest option for those wondering how to wear ankle boots with skinny jeans. Despite its practicality, we understand the ambivalent feeling of adopting dark and gloomy shades on sunny days. 

In that case, we recommend this stylish outfit composed of light-wash skinnies and burgundy boots.

Accentuated with a fuzzy blue trench coat, it’s definitely a lighter take on contemporary fashion. To top off the look, we suggest a matching purse with a dainty gold chain. 

Given the upsurge of Farrah Fawcett shag bangs and crochet clothing, it’s only natural for us to include a 70s-themed ensemble in our ‘how to wear ankle boots with jeans’ guide. 

This hippie-inspired outfit consists of a pair of mid-wash bell bottoms, a striped long sleeve turtleneck, and a set of brown heels.

Compared to the bright and bold aesthetic of Saturday Night Fever, this OOTD is considered a softer take on the disco scene. In terms of accessories, you can never go wrong with a pair of oversized shades. 

We’re fairly certain that Harry Styles’ wardrobe consists of jeans, ankle boots, and fun button-ups only. We can take inspiration from his daily fits, such as this classic ensemble. 

Composed of black skinnies, pointed toe zip-ups, and a gold-speckled shirt, this look is considered a great example of what soft rock celebrities typically wear.

The shaggy hair is totally optional, but we highly recommend accessorizing with gold-toned jewelry for a touch of bling. 

Blues will always be your go-tos’, but you should never underestimate the power of white jeans. Take, for instance, this outfit, which features a pair of bleached denim with a bright red Coca-Cola sweatshirt. 

Done in collaboration with menswear designer Daniel Fletcher, this playful look is reserved for those in the mood for a pop of color. It also comes with a stylish carry-on bag, which helps to blend this ‘how to wear ankle boots’ contender together. 

I know; we previously mentioned that ankle boots and jeans can never be worn formally. With that being said, this stylish outfit manages to pull it off. 

Considered part of the 2015 Saint Laurent menswear collection, this ensemble features a blend of mattes, sheens, blacks, and burgundy.

It’s relatively slick in silhouette, which bodes well with casual cocktail parties and networking events. For those still wondering how to wear boots with jeans, we suggest trying on this sleek and sophisticated fit out for size. 

The Canadian lumberjack look is not an aesthetic most trendsetters aspire to imbue. But, if done correctly, it can totally be an Instagrammable moment. 

Considered a great way to answer the ‘how to wear flat ankle boots with jeans’ question, this stylish outfit features a matching denim jacket and a pair of mid-wash pants.

It’s tailored in silhouette, which embodies a sense of class and sophistication. Trust me, this ensemble would not work if it was a mix of oversized shapes. 

Let’s be honest. The ‘f*ck off’ boots are a bit much, but it’s intrinsic to the Vetements brand. Considered part of the designer’s off-shoot Spring collection, this edge-lord edition speaks volumes of VTMNTS’ ‘I couldn’t care less’ attitude.

 It’s composed of a black graphic hoodie, a pair of faded jeans, and the ever-so-iconic boots. Complete with a set of shades, this is a look worth considering if you really (really) can’t be bothered with societal B.S. 

On Wednesdays we wear pink. With that being said, Regina George isn’t the author of this guide—so you’re free to wear this color whenever you want. For those looking to imbue that ‘plastic’ energy in a more contemporary manner, we suggest this chic outfit. 

It features a pair of dark-wash denim, a Barbie pink button-up, and a white crop top. Compared to Cady Heron’s look in the movie, I think it’s fair to say that this get-up is more flattering and fetch. 

Patchwork denim only had 5 minutes of fame in the TikTok spotlight, but that shouldn’t discourage anyone from sporting a pair now.

For instance, this stylish ensemble showcases a mix of grays and blacks for a more sophisticated look. 

Featuring a half-tucked button-up with a pair of faded denim, this ‘how to wear ankle boots with jeans’ contender is definitely a level-up from the usual combo.

The stiletto heels help to sharpen this intimidating image. Of course, the fanny pack and the choker necklace work to bolden the entire look as well. 

What Type Of Ankle Boots And Jeans Can You Get?

Fashion involves a frenzy of subcategories. Sure, you’re on the lookout for a pair of ankle boots—but what design are you after? Is the chunky platform silhouette, or is it the classic stiletto?

Of course, this also applies to jeans as well, as varieties differ in wash, cut, and shape. 

For those still wondering how to wear ankle boots with jeans, we’ll provide a short list of popular styles that are currently trending. 

Ankle boots:

  • The chunky heel: Considered a go-to for bar-hopping, there’s a reason why trendsetters prefer this boot style for longer days. It offers a wider degree of comfort. 
  • The ‘sharp’ silhouette: This includes pointed-toe styles and stilettos. It’s a sure-fire way to look sleek and sophisticated without the added effort. 
  • Platforms: Not a fan of heels? Flatforms and chunky silhouettes are considered the next best thing. Plus, it offers a boost of height for those 5’3” and under. 


  • High-waisted jeans: Aren’t blessed with long legs? If so, you can provide the illusion of height by wearing rib-cage jeans. 
  • Cigarette cut: tapered, slim, and considered more comfortable than skinnies, this style of jean keeps things sleek and roomy for casual days. 
  • Anything but traditional blue: if you’re in the mood for a pop of color, we recommend switching to pinks, oranges, and whites instead of classic blue. 

How To Choose The Best Ankle Boots and Jeans

Ankle boots and jeans are considered wardrobe basics. With that in mind, there’s a good chance you own a few pairs of both already.

But, for those who have yet to adopt this outfit into their closet, there are a few things to look out for when it comes to shopping.

Responsible buyers judge clothing and shoes based on five criteria: price, quality, material, fit, and design. 

High-quality jeans are constructed out of a blend of stiff and stretchy fabrics. This usually includes a mix of cotton, polyester, and elastane.

Shoppers should also be on the lookout for integrated features such as pockets and belt loops. Trust me, a large majority of women’s jeans are free of functional compartments. 

In terms of ankle boots, materials such as leather, lambskin, and merino wool ensure a sturdy and durable design. You should never opt for cheap textiles like vinyl, as there’s nothing more annoying than buying a new pair every season. 

Fit and design are two sides of the same coin. In short, they ensure continued wearability. A pair of ill-fitting jeans and ankle boots are practically doomed to the back of your closet, as nobody covets the baggy feeling of poorly tailored garments.

In addition, bright colors and daring silhouettes may not blend with the rest of your wardrobe if you consider yourself a casual dresser. Of course, this may not apply to maximalist trendsetters. 

In terms of price, a standard pair of jeans can cost anywhere from $60 to $200. This also applies to ankle boots as well. Prices vary depending on what brand you support and the allotted budget you’ve given yourself. 

How To Style Ankle Boots With Jeans

So, have you figured out how to wear ankle boots with jeans yet? To the casual dresser, it’s a simple go-to that doesn’t require any finessing. But, if you were to ask a veteran trendsetter, it’s a plain cake that needs a bit of ‘frosting.’ 

If you’re in need of fashion tips, we’ll share some advice for those in the mood for a bit of styling spice. 

  • Experiment with the cut of your jeans: if you currently subscribe to skinnies only, we recommend that you widen your fashion horizons. There are multiple cuts of jeans to choose from, such as bell-bottoms and cigarette pants. 
  • The ankle boot aesthetic: booties come in a variety of shapes, colors, and silhouettes. If you’re bored of your current style, chances are that you only own one pair of shoes. Why not switch things up a little by adding some Demonias with your Chelseas?
  • The classic belt: When we think of jean accessories, the first thing that comes to mind is the traditional belt. It’s a simple way to level up any denim-themed outfit. 
  • The coveted cuff: Are those Levis too long for your liking? If so, there’s nothing wrong with the simple double cuff. 

Fashion Tips To Avoid With Ankle Boots With Jeans

As aforementioned, ankle boots with jeans are the foundation of basic styling. It’s considered the blank canvas for outfit coordination.

Consequently, this leads to hundreds of ‘failed experiments.’ Don’t get me wrong, I’m all for wearing what you want—but you’d be surprised by the amount of fashion faux attributed to this classic combo. 

For those who’ve already figured out how to wear ankle boots with jeans, we’ll share some styling tips to avoid. 

  • The triple cuff: the basic double cuff is considered passable in the fashion world. But, for those who find themselves in the ‘triple-fold,’ their outfit is in danger of looking too bulky. 
  • Peep-toe boots: What’s the point in adding a minuscule toe window? It doesn’t show your pedicure properly. Plus, it’s a sure-fire way of inviting rocks and dirt while walking. 
  • Brightly colored socks: Don’t get me wrong; I love a pair of vibrantly patterned knits, but I tend to tuck in the opening when I wear boots. 
  • Anklets: there’s nothing more annoying than that ‘slap and clink’ sound as you walk. In addition, it’s super uncomfortable to wear under socks. 

How To Take Care Of Ankle Boots

Consider yourself briefed on the ‘how to wear ankle boots with jeans’ query. Now, it’s time to do some routine care and maintenance. If you own a pair of Demonias, Chelseas, or Doc Martens, chances are that you don’t want those $200+ to go down the drain.

We’ll show you how to clean your shoes at home using 4 easy tips. 

  • Eliminate surface-level debris with a microfiber cloth or a small brush. 
  • Remove stains with a dampened cloth. For suede shoes, we recommend a solution of diluted vinegar (or baking soda) in warm water. 
  • Polish with leather conditioner to retain its shine 
  • Store in a dry place. Make sure to stuff your boots with newspaper to help maintain their silhouette. 

Best Places To Buy Ankle Boots And Jeans

Take this as an opportunity to give yourself a pat on the back. You finally know how to wear ankle boots with jeans! If you’re in need of recommendations, we’ll highlight a few stores that are worth considering. 

Jeans: Reformation, AGOLDE, Levi’s, Wrangler

Ankle boots: Naked Wolfe, Doc Marten, Nordstrom, ASOS

Final Thoughts

Getting ready for the day requires a mix of creativity, motivation, and confidence. To the casual dresser, it’s just a matter of repeated outfits. 

The ol’ ankle boots and jeans combo is an understated go-to, but it can be so much more than a pair of skinnies and Chelseas. The fashion world is open to hundreds of possibilities. All you need is a bit of ingenuity and inspiration. 

Throughout our ‘how to wear ankle boots with jeans guide,’ we showed you 10 trendy outfits to consider. From patchwork denim to playful button-ups, there’s definitely no shortage of Instagramable ensembles on our list. 

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