How to wear ankle boots

If there’s a type of shoe that you can rely on through autumn and winter, it has got to be a pair of ankle boots. Cosy, comfortable and stylish there’s plenty of ways to wear ankle boots, from classic Chelsea boots for casual occasions to block heeled boots for smarter looks, there’s a pair to suit every lady and every outfit.

Ankle boots can be worn pretty much all year round and will work with almost everything you already have in your wardrobe. As it’s officially boot wearing season, we’ve put together a guide on the ankle boots to buy for autumn and what to wear with them.

Types of Ankle Boots 

Like all wardrobe staples, ankle boots come in an array of different shapes and styles, with a vast amount of ankle boots to choose from it’s important you pick a pair that will work with that will make the most out of your wardrobe. So, first thing’s first, let’s get to know the best types of ankle boots ...

Ladies Ankle Boot Styles

Men’s Ankle Boot Styles

Chelsea Boots

Best for: Smart casual looks, everyday, casual comfort

As classic as it gets, men's slip on Chelsea boots are a real investment, smart, stylish and easy to pull on they’ll look great with a range of trousers. To find the best Chelsea boots to suit the occasion, pull on a tan pair of boots with your blue denim jeans for a casual look and team black leather Chelsea boots with tailored trousers for a more formal finish.

Lace Ups

Best for: Smart, everyday casual, smart casual looks

Perhaps the most popular ankle boots for men, lace-up boots provide a lot of support at the ankle making them both practical and comfortable to wear. You can dress them for pretty much every occasion, from casual weekend days or refined and smart occasions. Men's chukka boots or desert boots, are a really classic way to style up your weekend outfits, they’re lightweight and flexible so they’re great for keeping you comfortable.

Walking Boots

Best for: Smart casual looks, everyday, casual comfort

If you’re heading out for a walk, you need the right pair of boots to suit the terrain. Just like lace-up boots, walking boots are designed to support your ankles while protecting you from rain and snow, while providing cushioned comfort that supports your feet on uneven ground.  

It’s best to opt for a lightweight pair to keep you nimble on your feet, and of course walking socks are the best way to keep you comfortable, just remember to accommodate for the thickness of the socks with a slightly wider or larger size of boot.

What to wear with ankle boots

One of the best things about ankle boots is that they are endlessly versatile. We’re not afraid to say it’s what we love most about the cold weather, their practical designs and flattering style means that it’s easy to finish any outfit with a sense of sophistication. Whether you’re wearing your ankle boots with your dressed down jeans, smart trousers, a skirt or a dress, ankle boots are the ultimate choice for Autumn, Winter, and maybe even Spring.

How to wear ankle boots 

The key to styling your ankle boots is to set out some simple style rules to create a perfectly polished outfit that is easy to throw on should the weather take a turn. 

• Styling the hems of your trousers is important when it comes to finishing your look. For skinny jeans and slim fit trousers, you should either tuck them into your boots or create a little turn-up so the hems sit just above the top of your boot as this will give the appearance of a longer leg.
• Match the colour of your boots to elements of your outfit and accessories, it will keep your look sophisticated and elegant.
• Remember, the darker the colour the smarter the boot. So, for casual looks opt for light colours like tan and go for blacks, dark browns, and navy for a smarter sign off.

How to wear ankle boots with jeans

Wearing ankle boots with your jeans is perhaps one of the easiest outfits for the colder months because they can be dressed up or down. For a weekend-ready look, put on a flat pair of ankle boots with your slim fit jeans and wear with plenty of layers to keep things cosy. A collared shirt and a knitted jumper make a great outfit option that will easily work with a brightly coloured tailored coat when you’re venturing out into the cold.

For a cosy option, look for pair of boots with knitted cuffs and tuck in the hems of your jeans. Not only is this a great way to incorporate some colour into your looks, but it will keep you feeling extra toasty. If you need to add more warmth, a thick pair of woolly ankle socks will lend a cosy finish.

As for dressing up your jeans for smarter occasions, go for a darker pair of ankle boots with black denim jeans for your base and liven up your look with a bright floral print blouse. Avoid tucking in the hems of your jeans here, let them sit just above the top of your boots as this will give a chic and elegant finish.

How to wear ankle boots with dresses

Ankle boots are perfect for pairing with your dresses when chosen well because they’ll lengthen the appearance of your leg. For a sophisticated look, opt for a midi-dress that will sit in the middle of your calf and match the colour of your ankle boots with a waist belt and bag.

For a more casual look in the colder weather, wear a knee length floral dress with a pair of woolly tights (opt for a brightly coloured pair if you want to go bold) and finish with a knitted cardigan to keep the chill at bay.