Style Guide: What To Wear With Ankle Boots - THE STYLE INSIDER

Ankle boots are the ultimate versatile shoe. When you swap your wardrobe around from season to season, your ankle boots stay in a prominent position exactly where they are.

Why? They’re a wardrobe staple that can be styled with everything from trousers to jeans to dresses and skirts of all lengths. When paired with the perfect outfit, they exude effortless style. You may be surprised to discover just how many options you have available when it comes to selecting an ankle boot.

Different styles work for various outfits – from casual to  effortless glam, all the way through to a more opulent dressy vibe. If you’re still unsure what to wear with ankle boots, don’t worry, we’ve put together this style guide to offer up some inspiration and show you just how easy it can be to get the look.


What types of ankle boots are there

Before we get started with the finer details, it will pay to keep in mind the height of where the boot lands on your ankle. Some sit lower, some higher and some ankle boots have wider openings than others. Many boots are perfect for tucking jeans into because they have a wider opening. The way in which you dress your ankle boot can create gorgeous long lines with your legs and accentuate the ankle, which is the slimmest point. Your styling options are diverse with ankle boots, purely due to how many types of footwear you have to choose from. So let’s take a look.


Boots with a flat heel or no heel at all look fabulous with flowy dresses and A-line shapes. When styled in the correct way, this type of boot can also look great with jean legs rolled up or shorts when the weather is warmer. By nature, flat or no heel boots do tend to have a more relaxed, bohemian feel so they’re perfect for casual occasions. However, if you’re looking for a more high-end, luxurious look go for a leather boot with a pointed toe to take you into the evening with ease.

UGG Aureo


UGG Bandara


This type of boot is probably the most accessible and wearable of the bunch. The heel is high enough to make you stand up tall and accentuate your curves, while also being low enough to be comfortable for all-day wear. They can also be worn with most items of clothing – all lengths of dresses and skirts, as well as jeans and trousers – all great options to wear with a low block heel. Give your jeans a double roll at the bottom to reveal a subtle flash of ankle and you’re onto a winner.


A higher heel brings with it a dressier finish, elongating your whole body, and improving your posture. It depends on the height of heel you feel comfortable with as to whether you opt for a low or high heel. Again, these boots really do go well with any outfit and they add extra femininity, class and elegance along the way.

Woman in Black Shirt and Blazer Sitting on White and Brown Wooden Chair


Woman Holding Her Jeans

Wedge heels are a touch more limiting with what they can be paired with. They do, however, offer a fantastic alternative to other heels if you want extra comfort or just something a little different. In some cases, they can be worn instead of other ankle boots, but you will need to experiment with what suits you when it comes to a wedge heel boot.


This type of heeled boot offers up a lavish, glamorous look, they’re better suited to evening wear or a more upscale daytime look. The thin heel adds an edgier vibe, look for patent leather this season to tap into upcoming luxe inspired trends.


Photo of Woman Wearing Plaid Skirt

Open-toed ankle boots make the transition from the warmer months into autumn and winter seamless. They’re perfect with elegant tea dresses in the summer or a fitted playsuit when the temperature drops. Boots with pointed toes offer a more opulent and glamorous option no matter the material or colour. On the other hand, boots with a rounded toe can cross over in the categories of casual and dressy depending on the material and heel height.


You’ll find a myriad of options when it comes to the colour and finish of your ankle boots. But the main, versatile colour finishes you could choose from are black, grey and brown in a variety of shades. If you want to get adventurous with pops of flamboyant colour, choosing a bright hue adds an eye-catching finish to any outfit. Animal print ankle boots are also a fabulous on-trend choice to beautifully upgrade a look. Both leather and suede finishes are popular – leather can offer a more polished look while suede offers a casual-cool finish.


  1. An all-black outfit
  2. A skirt above the knee
  3. A midi or maxi length dress
  4. Your favourite jeans
  5. Floral print dresses
  6. Classic jeans and a t-shirt

We’ve pulled together a list of our favourite ankle boot looks to inspire you for the year ahead.


Lengthen your legs by wearing a black ankle boot with black tights, leggings, jeans or trousers. This is the perfect opportunity to embrace an all-black look and have fun with the winter 2018/19 trend of layering for an overall effortlessly chic, yet edgy, look. You know what they say – if you can’t find something to wear, then wear black!

Rob’s Top Tip: Play with layers of different lengths and textures for a fabulous finish. If you feel like your all-black ensemble needs lifting, add accents of animal print with a few accessories.


Great Plains Jersey Top

Great Plains Ripple Jersey Pleated Hem Top
Abellana Bomber Jacket
French Connection Abellana Bomber Jacket

French Connection Rebound Skinny Jeans
French Connection Rebound Skinny Jeans
Mharia Circular Heel Ankle Boots
Ted Baker Mharia Circular Heel Ankle Boots

Two Women Standing Beside Wall at Daytime


Showcase your legs with a dress or skirt that falls above the knee. The fabulous thing about this length of skirt means it can give off a more casual vibe or an evening look, depending on how you dress it. We love an edgy leather jacket and ankle boot pairing contrasted with a feminine floral dress.

Rob’s Top Tip: Make this look transition from season to season with the addition of tights and lightweight jackets through to heavier coats to protect you from the elements.


French Connection Aubine Drape Dress
French Connection Aubine Drape Dress

Junique1 Biker Jacket
Boss Casual Junique1 Biker Jacket

Elysian Boot
UGG Elysian Boot


In the autumn months, create a fabulously feminine outfit with either a closed or peep toe boot and a pleated midi skirt with a chic jumper tucked in. In the summer, pair a midi dress or skirt with a cami top and have a lightweight jacket to hand. Or you could take a rebellious tone with your style by pairing a long dress with edgy combat or flat ankle boots. So many possibilities!

Rob’s top tip: A midi-length hemline teamed with cute ankle boots is the absolute ideal outfit to transition between seasons. Have fun experimenting with this look.

Photo of Black Patent Leather Boots


Roll up or cuff your jeans so that your ankles peek out (this also looks striking with the previously mentioned all-black layering) or you could tuck your jeans into the boots for another super chic and effortlessly cool look. This works with all heel heights and what you choose totally depends on the overall finish you’re looking for from your ensemble. If you’re going for cocktails with the girls, opting for a higher heel would be perfect but if you’re going shopping for the day choose a lower heel for comfortable style. Adding a tote bag completes this look with style.

Rob’s Top Tip: Tucking your jeans into your ankle boot can create a long, lean leg line while cuffing them slightly can highlight slim ankles.


Bell Sleeve Wool Blend Sweater
Armani Exchange Bell Sleeve Wool Blend Sweater

Australia Keller Croco Boots
UGG Australia Keller Croco Boots
Sophia Skinny Jeans
Superdry Sophia Skinny Jeans


Tote Bag
Armani Exchange Tote Bag


Floral dresses with ankle boots are the ultimate mix of feminine style and edgy glam. In the summer keep a light or leather jacket to hand to pair with as the temperature cools. As the season transitions, layer the look by wearing the dress and boots with tights and a long wool coat.

Rob’s Top Tip: This look can work for both the office and a night out with subtle changes in accessories. Add a cute crossbody bag with a delicate chain to make this look translate into the evening with ease.


Linosa Crinkle Off The Shoulder Maxi Dress
French Connection Linosa Crinkle Off The Shoulder Maxi Dress
Liveca Elastic Detail Leather Ankle Boots
Ted Baker Liveca Elastic Detail Leather Ankle Boots
Core Coating Long Belted Mac
Great Plains Core Coating Long Belted Mac
Doriis Bow Detail Micro Xbody
Ted Baker Doriis Bow Detail Micro Xbody


Woman Sitting on Ground Leaning Against Tree
Woman Standing While Holding Black Tote Bag

These looks feature clever layering for cosy-yet-chic styling options. Pairing your boots with jeans and a casual tee leaves a fantastic canvas to layer over the top with. For an ultra cool and casual vibe choose a denim jacket, leather backpack and a scarf. For a more polished finish select a trench, chic wide brim hat and a tote. As this is a more casual look, keep in mind that plaid is in vogue for winter 2018/19 – the addition of a plaid shirt or scarf would look gorgeous with either of these outfit choices.

Rob’s Top Tip: Both of these looks are fabulous for year-round casual style. As the w