How to Wear Ankle Boots

There’s one thing you simply can’t go wrong with: ankle boots. Every woman should have at least one pair because not only are they comfortable, they look fabulous on you, too.

They are a small boot that covers the foot and rises up to the ankle, this can sometimes cover the ankle and occasionally be worn half way up the calf. They can be heeled, stiletto-boots or they can be flat. Their versatility means that you’ll have a pair for every occasion. Whether you’re in need of cushioned, waterproof, fleece-lined or bold shoes, the ankle boot has got you covered.

As well as this, you can wear them with practically anything! A Summer dress, mom jeans, skinny jeans, tailored pants, chinos, culottes, cropped jeans, skirt and tights, you name it. Some have even worn them with their birthday suit (only at home, guys!).

We’re here to provide you with some glamourous, powerful and edgy style ideas that you can try out. Of course, like with any style, it will be a trial and error scenario, but that’s the fun of it. So, let’s get trending!

The Shopaholic

This is the everyday get up, normal style chelsea boots with a casual pair of jeans or leggings. If you fancy tucking your jeans in, go for it. if you want to have your socks poking out of the top, we’re loving it!

They can be any style, colour or material you can think of because they’re you. The shopaholic needs to be smart; spending a day walking around your local mall or town centre, you’re going to want a pair of comfy shoes. The classic chelsea is here for you, flat, well-lined and covering your foot in the best way possible.

You’ll be ready for all types of weather, if it snows, rains or shines. And, they’ll pair with anything from jeans to leggings to trousers, rolled 1-2 inches or tucked in. it’s up to you to try out some looks and find which one(s) work for you!

Another benefit to the classic shopaholic look is the colour spectrum you have. Of course there’s the traditional black or brown pair, but there’s also the leopard print pair, the pink pair or the emerald green pair. Be adventurous and strut your stuff down the high-street.

 The Office Chic

The one is questioned a lot in the fashion community. “Can I really wear ankle boots to the office?” Yes!

There are so many different breeds of ankle booties, that you’ll have plenty to choose from. We recommend keeping the professional style of flat ankle boots, (or small heel) with a rolled-up tailored trouser. Make sure there’s no socks poking out in this get-up because you’ll want to remain sleek.

We want you to be able to have comfy footwear in an office, so have a little look at some black, flat ankle boots that have a subtle point to the toe and maybe a couple of gold embellishments on the side/zip.

This look pairs fantastically with a duster coat and a handbag of the same colour as your boots! Have a nice tucked-in blouse and you’re good to go. There’s no need to be stood in uncomfortable office heels when you could wear a simple and youthful pair of ankle boots.

The Rodeo Gal

For a more bohemian style, you could always pair your ankle boots with a dress and sunhat. As trends are always coming back around, you can’t go wrong with the 60’s inspired boho look. Think, brown boots with a sprinkle of cowgirl, but not so much that you’re automatically yelling “Yeehaw!” at the end of every sentence.

Flowing dresses accessorized with flower crowns, flower anklets that droop over your lovely boots: It’s all about bringing your personality into your look.

Or, you could pair a lovely pair of blush pink faux suede ankle boots with a long Summer dress. The options really are endless! But, please, we urge you, do not be tempted by peep-toe ankle boots. Let’s not go there.

So, really the point would be that even if you’re up for a dress or a skirt-and-tights kind of day, your ankle boots will be there for every stride.

 The Date Night Ensemble

Here we have a special pair of boots, the pair that’s going to make them come back for rounds two, three, four and more.

Without putting too much pressure on these shoes, they will be the heeled pair of boots, perhaps a faux suede paired with those jazzy cut-off pants that have been hiding in the back of your closet for far too long.

There’s gorgeous styles of ankle boots on the market that have cut-outs going from the top of your boot down your foot. These provide a taste of your sexy side because they can elongate and show leading lines for a leading lady.

Maybe even go for the pair with a little sparkle just to show your adventurous side. Don’t forget, your ankle boot is your personality. Even for men; you can’t beat a good pair of chelsea boots on a man, and when your boots are hitting it off better than you on your date, you know you’ve found your match!

The “Why Am I Still Out at This Time?”

A pair of skinny black pleather (because we’re all about saving our furry friends!) trousers tucked into some dazzling night-out ankle boots and you’re off. Don’t worry, we know you’ll pull those trousers off!

Think of the highly patterned and embellished booties with the block heel to get you through the night. This look is best paired with a lovely white blouse and accessorized with things like long necklaces, large earrings, equally-dazzling handbags and a bandana.

If you’re questioning why we are saying bandana, have a look at our other article “How to Wear a Bandana” for tips and tricks on how to style!

Even if you don’t have a pair of bedazzled ankle boots to hand, if you have an old pair of boots you think could be upcycled, try bedazzling them yourself! We advise grabbing some cubic zirconia gemstones, a hot glue gun and a glass of wine for the fun-factor.

 The Outside Slippers

So, we’ve already told you that ankle boots can come in all shapes and sizes, but, they can also come with all types of inner lining. You can have cotton or faux sheep’s wool to keep your toesies warm in the Winter. Or, you have thin line or no line (cropped wellie boots) for the Summer months.

These can be used anywhere from shopping to the school run, from gardening to a date. Perhaps a third or fourth encounter, after you’ve worn your date night ensemble boots!

Your outside slippers should feel like you’re walking on clouds, allowing you to walk around for long periods of time without the hassle of heel pain, blisters or toe-pinching.

Again, these can be paired with almost anything. Many would even wear them with their sports clothing to get to and from the sports destination. For example, we recommend slipping your outdoor slippers on after a fun day skiing down some slopes, or even after a long-distance run.


Consider pairing your outside slippers with some tucked-in skinny jeans, cropped leg or rolled hem jeans with a comfortable top and you’ll be good to go. You may as well attach a pillow to your head, too.

 How Not to Wear Your Ankle Boots:

  • As long boots
  • As flip flops
  • On your hands
  • On your head
  • On your dog

A final note from us, would be to say that the flexibility that ankle boots provides is endless, including for the areas you can’t see. Every woman is perfect in their own way and we all have our own niggles. So, if you need orthotics for flat feet, extra cushions for high arches or even if you have a pedicure that went wrong. The ankle boot is the perfect answer, allowing room for everyone.


So, there you have it, 6 style ideas on how to wear ankle boots. There’s more out there and there’s plenty of personal editions that you should add to make the look more you. But, for now have a shop around and test some of these stylish get-ups and see how they fit you!