How to Wear Ankle Boots & Ankle Boot Styles

September 30, 2025

How to Wear Ankle Boots & Ankle Boot Styles

There are so many ways to wear women's ankle boots ‐ because there are a number of different styles to choose from. Comfort is important, as is matching the right types of ankle boot to the right occasion. Find out more in our expert guide.

Best Women’s Ankle Boot Styles

Kitten Heel Boots

Best for: work, interviews and everyday casual

Kitten heels tend to be quite thin, but are still stable and easy to walk in – because the heels tend to be under two inches. The small heel adds a touch of elegance compared to flat boots. They’re perfect for pairing with tailored trousers, dresses, or even jeans if you want to smarten up a simple look.

Wedge Heel Boots

Best for: everyday comfort and stability

While wedge heels tend to be a little taller than kitten heels, they’re still easy to walk in due to the lack of a gap between the toe and heel of the shoe. Wedge heel boots support your entire foot and give you more contact with the ground, providing more stability. Pair with skinny jeans or leggings and a longline knit for a sleek but cosy outfit.

Chunky or Block Heel Boots

Best for: work and job interviews

Chunky or block heeled boots are also a great choice for comfort, as they give your heel more surface area and protection. While they aren’t as stable as wedges, they’re much more so than, say, stilettos. Because of the elegant look they provide, chunky and block heel ankle boots are great to wear for work or a job interview.

Open or Peep Toe Boots

Best for: weddings, parties and special occasions

When fitted correctly, open or peep toe boots can be super stylish – allowing your pedicure to add a hint of glamour to your outfit. This makes open and peep toe ankle boots perfect for weddings, parties and other special occasions. They pair well with cuffed trousers, skirts and dresses.

Flat Ankle Boots

Best for: everyday comfort and casual wear

When it comes to ankle boot styles, these are by far the most comfortable and relaxed. Ankle boots can pretty much be paired with whatever outfit you have on – and are in their element on cold or rainy days. Team with anything from jeans and dresses to skirts and tights.

Lace Up Ankle Boots

Best for: work or special occasions, depending on the style

Womens lace up ankle boots come in many styles, from flat to peep toe. The laces can be adjusted for the perfect fit. However, be careful how tight the laces are – especially around the ankle area. As the day goes on and your feet swell, tight lacing can cause numbness and pain in your foot. Depending on the style of your lace up boots, they could be a good option to wear to work or to a special occasion. Just check they look right with your outfit first.

Buckle or Strap Boots

Best for: everyday support

Buckle or strap boots generally provide more support to your ankle than slip on boots. Make sure to check the strap can be adjusted to your size, and isn’t too big or too small.

• Too big won’t provide much support and could hurt your ankles.
• Too small could lead to numbness in your ankles and feet.

Tassel Boots

Best for: making a style statement

Tassel boots don’t usually add anything to the fit of the boot. However, when paired with the right outfit they can add a stylish detail that completes your look.

How to Style Ankle Boots

Knowing the types is one thing, but how do you actually wear ankle boots? Here are some outfit ideas to help you get started.

• With Jeans: Skinny jeans or straight-leg jeans look great tucked into ankle boots. Cropped jeans also work well with heeled styles, letting the boots shine.
• With Dresses: Short dresses pair nicely with flat or heeled boots, while midi dresses balance out chunkier boot styles.
• With Skirts: Ankle boots with A-line or pencil skirts make for a stylish smart-casual combo. For a coordinated look, match the colour of your boots with your tights.
• With Workwear: Go for block heels or sleek Chelsea boots with tailored trousers and a blazer for an office-ready outfit.
• By Season: In autumn, pair boots with layers like knitwear and scarves. In spring, go lighter with dresses and ankle boots in tan or pastel tones.

How to Wear Ankle Boots Over 40

The key to wearing ankle boots over 40 is finding a boot that suits your shape and sense of style. Make sure:

• The hem of your jeans is no more than an inch off the ground when wearing them with bootcut jeans.
• If wearing ankle boots with a skirt, that it’s no shorter than knee length.
• The colour of your boots matches your outfit. Wearing boots that are the same colour as your tights or skirt will help keep your look understated and elegant. Why not try pairing brown ankle boots with neutral tailored trousers?

How to Wear Ankle Boots Over 50

Ankle boots are one of the best pairs of shoes to wear if you’re over 50. There are a range of ankle boot types and styles that could work for you, including:

• Flat ankle boots – one of the more versatile styles which will go with any look or outfit.
• Tasselled or buckled ankle boots – these can add an extra detail to a simple, everyday look like skinny jeans and a shirt.

Our comprehensive style guide has all the information you need on how to wear ankle boots over 50.

Men’s Ankle Boot Styles

Lace Ups

Best for: work and special occasions

Lace up boots are a popular choice for men, because they provide a lot of support – especially to the ankle – and are comfortable to wear. Lace up boots can also look refined and professional, making them a great option for work and special occasions.

Chelsea Boots

Best for: work, weddings and smart casual looks

Chelsea boots are stylish and smart pull-on boots. These iconic shoes have been fashionable for decades. They look great with smart trousers for work, interviews and special occasions – and also go well with jeans for more of a smart-casual look.

Desert Boots

Best for: everyday, casual comfort

Desert boots, otherwise known as Chukka boots, are lace up boots usually made of suede or imitation suede. These lightweight, casual boots are great for weekend and light work wear.

Walking Boots

Best for: outdoor activities like walking and hiking

Walking boots, or hiking boots, are just like normal lace up boots but with more comfort. Designed to protect your ankles and cushion your foot, they also guard your feet against rain and uneven ground.

Finding the right ankle boot type can be a hefty task, so try plenty of different options on before deciding what’s right for you. If you’re still unsure on how to wear ankle boots with your favourite outfits, take a look at our style guide.

Our Top Ankle Boot Picks

For Womens

• Lilley Brown Chelsea Boot - A timeless slip-on boot that transitions effortlessly from office wear to evening outfits.
• Hush Puppies Brown Leather Boot - Country-inspired and casual, these pair perfectly with floral dresses or skirts.
• Lilley Lace Up Boot - Cosy knitted trim makes these a winter staple with jeans and chunky knits.

For Men

• Beckett Chelsea Boot - Sleek tan Chelsea boots ideal for smart or smart-casual outfits.
• Relife Brown Zip Up Boot - With a rugged design and fleecy lining, these boots blend heritage style with cold-weather comfort.
• Urban Territory Brown Hiker Boot - Practical walking boots with style to spare – great with jeans and outdoor layers.

Styling Ankle Boots FAQs

Are ankle boots still in style in 2025?

Yes! Ankle boots remain a wardrobe essential because of their versatility. Whether flat, heeled, or embellished, they work across all seasons and occasions.

Can you wear ankle boots with skinny jeans?

Absolutely. Skinny jeans tuck neatly into ankle boots, showing off their shape. To elongate your legs, pair dark jeans with matching dark boots.

What socks or tights should I wear with ankle boots?

For a seamless look, match tights or socks to the colour of your boots. In colder months, try cosy patterned socks that peek over the top for a playful detail.

Check out the shoezone blog for more style tips and footwear suggestions for every occasion.