How To Wear Ankle Boots

Mmm, fall: the season for pumpkin spice lattes, oversized blanket scarves, and lots of cable-knit sweaters. Of course, no autumn outfit is complete without a pair of ankle booties. 

Preferably black and chunky in the heel, these cold-season shoes do wonders in accentuating your look. Obviously, you’re free to wear them during spring and summer, but let’s be real—September to February are the peak months to enjoy ankle boots. 

If you require some styling inspo, we’ll show you how to wear ankle boots. We’ve gathered 16 different outfit ideas to choose from, and don’t worry—these fits are universal. 

What is an Ankle Boot

Unless you’ve been living under a rock, ankle boots are shoes cut to, well, the ankle! They’re usually made out of leather and synthetic materials.

Typically, most trendsetters gravitate to chunky heels, but we’re now seeing an upsurge on exaggerated, flat-footed platforms. 

History of Ankle Boots

For those who have a deep appreciation for the coveted ankle boot, I think a bit of history can help accentuate your love even further. The earliest mention of the shoe was recorded back in the prehistoric ages.

Cave paintings, murals, and other cultural etchings depicted people wearing animal skin boots. 

In the years to come, ancient civilizations located in Egypt, Asia, and Greece came to adopt the boot as a wardrobe essential. It signified the upper class for the Romans, as most came adorned with jewels and embroidery.

In the following eras, boots were synonymous with military uniforms, working attire, and sports riding. 

The earliest rendition of the ankle boot is traced back to the fifteenth century. With that being said, they didn’t become popular until the nineteenth century, when they were worn casually. 

The 1800s saw the birth of the Adelaide heel, which offered a heelless design with intricate lacing. You’re probably familiar with the famous Victorian ankle boot, which was fashioned by the likes of Queen Victoria and Prince Albert.

When to Wear Ankle Boots

As we mentioned before, the ankle boot is commonly worn during the cold season. They’re insulated, highly practical for slushy sidewalks, and uncomplicated to put on compared to knee-high booties.

Of course, you don’t have to wear ankle boots exclusively for fall and winter. With that being said, there’s a reason why most of us opt for sandals and slippers during July. 

If you’re wondering how to wear ankle boots, you should know that they can be fashioned casually and formally. Don’t worry; we’ll provide some styling tips to help readers get started. 

How to Wear Ankle Boots

There are multiple ways to style ankle boots. If you’re looking for something super safe, the classic jeans, tee, and leather jacket combo can never go wrong.

But, chances are that you clicked on this ‘how to wear ankle boots’ article looking for other outfit ideas—and we’re here to do just that! Below, we’ll share 16 OOTDs that you should definitely consider wearing out. 

9 Outfit Ideas with Ankle Boots for Women

Cowgirl-chic is not a look anybody can pull off—especially if it’s the dead of winter. Instead of opting for chaps and a fringe jacket, we suggest a more casual ensemble composed of cigarette pants, a black puffer jacket, and a pair of sunnies. 

This is a great outfit to wear if you’re wondering how to wear ankle boots with jeans. We highly recommend finishing off the look with a matching crossbody bag. 

If the weatherman calls for 5 inches of snow, perhaps it’s best to leave your stilettos behind. As a better alternative, we recommend basing your outfit on a pair of platform ankle boots. 

If the shoes come in the classic ‘sock’ silhouette, a set of wide-legged pants and a loose trench coat can help balance your proportions out. Take it from Zoë Kravitz, who is absolutely rocking this look with some added sunnies. 

Most of us wonder how to wear boots with jeans. It’s the safest of styling options, as the risk of outfit clashing is downsized to a 0. But, for those looking to up their fashion game, we suggest turning the tables by wearing a floral number. 

The grunge-themed boots pair well with the feminine silhouette of the midi dress. To help tie the look together, we recommend throwing a leather jacket on top. 

I’m 100% sure that Miranda Priestly wore this look during the Devil Wears Prada. If not, it definitely screams ‘fashion editor’ to me due to the tucked sweater and the cheetah-print skirt.

The sunnies and matching belt help to blend the top and bottom together. In our humble opinion, this is the ensemble to opt for if you’re looking for how to wear ankle boots over 40. 

For us girls, our go-to pants will always be the coveted legging. It’s the sexier version of sweatpants due to its skin-tight fit. 

If you’re wondering how to wear ankle boots with your Lululemons, we suggest keeping things classy with an oversized hoodie and bomber jacket. A clutch bag and a pair of sunnies can help elevate the entire look unless you’re keen on the ‘couch potato’ aesthetic. 

2022: the year of the oversized blazer trend. Considering that it’s the hottest fad on social media, it’s only natural for us to include it in our ‘how to wear ankle boots’ lineup. 

This outfit is composed of a leather jacket, a matching black dress, a Louis Vuitton crossbody bag, and of course—a pair of flat-footed stompers. It’s certainly the ensemble to opt for if you’re looking to up your Instagram feed. 

Ankle boots with jeans will always be a classic combo. But, I’m sure most of you have done this outfit to death. 

For a fun spin, a printed zip-up sweater and a pair of wide-legged jeans are considered a more elevated take on this outdated trend.

If you’re wondering how to wear ankle boots that are white, it’s usually best to match them with something that’s equally as bright, whether that be a color or pattern. 

Considered another great example of fashion juxtaposition, this daring outfit combines springtime romance with hardcore grunge. It’s definitely a daring look to pull off, but we highly recommend it for trendsetters looking to shock.

As an added accessory, we suggest a black crossbody bag and some statement jewelry for extra pizazz. 

Leather on leather is certainly a bold choice to make, but it’s an excellent look if you want to imbue those subtle ‘femme fatale vibes.’ The outfit features a puffy white blouse and a body-con midi dress. 

The thigh-high slit may spell danger for random winds, but it can easily be remedied by wearing some tights underneath. The ankle boots are the real star of the show, as they come with lace-up details and a pointed toe. 

7 Outfit Ideas with Ankle Boots for Men

Dr. Martens are usually the go-to choice for the winter season. They’re durable, practical to wear, and timeless in style. Since most gravitate to grunge clothing to match their platform boots, we suggest opting for a ‘hot’ outfit composed of a flame-printed sweater and matching jeans.

The beanie is absolutely necessary to complete this entire look. 

Something about this outfit gives me ‘New York City coffee boy’ vibes. It’s a bit pretentious, but we can’t deny that it’s a solid look. 

This urban-chic ensemble is undoubtedly an elegant take on modern streetwear, composed of a leather jacket, a mock-neck tee, and two-toned jeans.

The ankle boots add that extra ‘umph’ to the ensemble. Of course, you can always swap them out for Converses if you’re nearing the end of winter. 

For those Googling ‘how to wear ankle boots with straight leg jeans,’ this is the outfit to opt for. It’s a smart look composed of tailored white pants, a printed cardigan, and a crew neck t-shirt to help give off that layered effect. 

The platform shoes embody a sort of ‘art-school’ feel to the entire ensemble. If they were substituted with oxfords, they would definitely scream ‘my daddy pays for my tuition’ vibes—which is not what we want. 

I get it; not all of us can pull off hardcore grunge or skater boy-chic. If you’re into soft pastels and looser silhouettes, we suggest a more romantic fit composed of black shorts and a striped sweater. 

It’s absolutely necessary to find an oversized pullover, as it’ll help imbue those demure and innocent vibes to your entire look. This is how to wear ankle boots for those not keen on dark and brooding aesthetics. 

The “how to wear ankle boots’ question can easily be answered by figuring out the aesthetic of your shoes. If they’re chunky, why not compose a cohesive fit that’s also bulky? 

As an example, this ensemble features a baggy pair of jeans, a puffy cream sweater, and an oversized knit beanie. Don’t forget to accessorize with a matching necklace and stud earrings if you’re feeling especially extra. 

This outfit is definitely giving me Ryan Tedder vibes due to the fedora and matching scarf. If you want to cop that ‘musician fit, we highly recommend wearing a well-fitted trench coat, a crew neck t-shirt, dark-wash jeans, and brown leather lace-ups. 

It’s an excellent look if you love the hipster scene. Of course, the wide-frame glasses are optional, but they help blend the whole look together. 

Men can pull over flannel blazers too. Take, for instance, this outfit, which is composed of a well-fitted jacket, straight-legged jeans, a white tee, and a black cardigan underneath.

Dr. Martens are an absolute must if you’re going for an elegant streetwear look. 

But, for those searching for something more office-appropriate, you can always sub out the ankle boots with loafers instead. 

What Type of Ankle Boots Can You Get?

Ankle boots come in all shapes and sizes. If you want to find your coveted pair, you’ll need to assess your personal tastes and needs. For instance, if you prefer minimalism, we suggest opting for a simple set of pointed boots.

On the other hand, those who love the grunge vintage scene may find platform shoes as a better option. 

Before you answer the ‘how to wear ankle boots’ question, we’ll feature some classic designs worth considering:

  • The stiletto heel 
  • The chunky platforms 
  • The classic Victorian boot 
  • The good ol’ reliable Chelseas 
  • Combat lace-up boots 
  • The classic pair of Uggs 
  • Sock boots 
  • Timberlands 

How to Choose The Best Ankle Boots

Let’s be honest; a $15 pair of cheap ankle boots isn’t going to win any awards in durability. Fast fashion retailers will typically cut corners in order to provide affordability.

Of course, by no means are we suggesting that you invest in a $1,000 pair of designer kicks. There are multiple footwear stores that offer high-quality ankle boots for around $100 to $200

A good pair of stompers should be constructed out of premium leather, durable synthetics, and suede. In terms of lining, most reputable companies use merino wool, cotton, silk, or polyester on the inside. 

It’s worth noting that some ankle boots are strictly designed for harsh weather conditions. If you live in icy climates, we suggest looking out for shoes that come with steel toes and snow grips. 

How to Style Ankle Boots

Figuring out how to wear ankle boots shouldn’t be a frustrating task. If you’re at a loss of what to do, there are some general tips that trendsetters can use to form an outfit. Based on the ensembles we’ve featured so far, here are some common styles worn with ankle boots:

  • The oversized blazer/puffer jacket: the exaggerated silhouette of these jackets pairs well with the slim-fit nature of ankle boots. Of course, you don’t have to fork over $400 for a well-made blazer, as you can easily find one at your local thrift store. 
  • Cigarette and wide-leg jeans: long gone are the days of skinny jeans. That accentuated ‘flare’ looks absolutely great with a pair of ankle boots. And best of all, it requires no tucking. 
  • Dresses and midi skirts: the grunge-themed aesthetic of ankle boots works well with the feminine attributes of floral patterns and flowy dresses. It’s a great example of fashion juxtaposition. 
  • Sunglasses: Let’s be honest; the ankle boot is an intimidating look to pull off. If you’re looking to imbue those ‘don’t look at me vibes,’ a pair of sunnies can help strengthen those boss babe vibes. 

Fashion Tips to Avoid With Ankle Boots

If you’re an ankle boot believer, you should already be familiar with some ‘fashion sins.’ The classic stomper can look odd and out-of-place if styled incorrectly. Below, we’ll feature a few outfit no-nos to consider the next time you wear a pair of classic stompers. 

  • The clog rain boots: Popularized by Bottega Veneta, these shoes should probably remain on the runway. They offer a childish vibe, and it’s certainly a hard piece to accessorize if you’re a novice dresser. 
  • Mini skirts: Don’t get me wrong; this can definitely work if you wear some black tights underneath. Those who choose the ‘bare option’ are at risk of looking too top-heavy.
  • Socks that peek over the edge: if you’re wearing ankle boots, make sure to find a pair of short socks. Wearing a set that’s too long can offer an odd pop of color to your fit, especially if it’s a wild print. 
  • Know when to tuck in your ankle boots: Some designs come with a tight sock fit or a loose open hem. Obviously, if you wear flared jeans, there’s no need for extra tucking.
  • The open-toe boots: believe me, if you live in snowy climates—the thought of slush and dirt creeping into your peep toe is a nightmare you don’t want to live. And no, socks can’t be worn as extra protection. 

How to Take Care of Ankle Boots

High-quality ankle boots don’t run cheap. If you’re keen on wearing them forever, it’s best to implement some routine maintenance.

I’m sure not all of us have the time to visit our local cleaner, which is why we’ll offer some tips and tricks on how to take care of your ankle boots at home:

  • When wearing them, stay away from puddles, snowbanks, and dirt spots to help maintain their quality. 
  • Leather shoes often require a conditioner to help preserve their texture and flexibility.
  • Use salt removers (or a mix of water and white vinegar) to remove salt stains from suede boots.
  • Add a protective sole to increase the longevity of your ankle boots.
  • Use a boot shaper to maintain the silhouette of your shoes. Of course, newspaper and foam will also do the trick. 

Best Places to Buy Ankle Boots

So, you’ve figured out how to wear ankle boots, now it’s time to buy a pair. For those in search of their perfect fit, we’ll feature some boutiques and stores to support:

  • Nordstrom 
  • Amazon 
  • Browns 
  • ASOS
  • Little Burgundy 
  • ALDO
  • Dr. Martens 

Final Thoughts

Ankle boots are not a passing fad. On the contrary, they’re a wardrobe staple, which is why it’s necessary to invest in a high-quality pair.

Obviously, you don’t need to own 50 sets of stompers in order to look fashionable, as you can make do with just one. 

From super casual to dressed to impress, we shared 12 of the best ensembles to wear with ankle boots. Hopefully, you’ve gathered enough inspiration to create a cohesive fit of your own. 

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