How To Wear Ankle Boots All Year Round

by Freya Wilcox
Grey ankle boots and black jeans on marble surface

Comfortable, stylish and versatile – ankle boots are a flattering wardrobe staple at all times of the year. Whether you’re contemplating buying your first pair, wondering what to wear with tan ankle boots, or just looking for some style inspiration, we’ve got the must-read guide on how to wear shoe boots all year round.

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Autumn/Winter Trends

As the nights draw in and the days get colder, putting your feet back into ankle boots most definitely eases the pain! If you’ve ever wondered how to style your wintery outfit with ankle boots or what shoes to wear with skinny jeans, going for a pair that sit at the ankle is both flattering and certainly suits the season.

Black, tan and brown coloured boots are great transitional colours for autumn into winter. We also love the fact that when the darker colours come out of the wardrobe, you can have more fun with your footwear. Go for leopard print, studs, velvet, frills or embroidery – these styles of ankle boots with skinny jeans work so well and the celebs are loving them.

A/W Inspo: Jeans and Boots

In terms of how to style your skinny jeans and ankle boots, go for black or blue denim jeans, tucked in. These colours really work with brown shades, meaning you never need ask how to wear brown ankle boots again!

If you’re thinking of a boyfriend or bootcut pair of jeans at this time of year, don’t try and tuck them into the boots (nightmare!). Instead, roll up your jeans slightly to reveal cute, frilly socks sitting just above the ankle, or go for some frayed edges that are particularly stylish right now. Both of these looks will really show off any embellishments on your boots or that cute, feminine heel (perhaps both together, but more on that in our top 15!).

A/W Inspo: Boots to Wear With Dresses

Tan coloured ankle boots with dresses and thick tights are a winter winner – think autumnal colours to complement the change of season; but if you’re wearing a pattern on the top, it’s best to keep the boots more minimalist.

A/W Inspo: What to Wear With Black Boots

Praise be the black boot: a perennial wardrobe favourite. Indeed, when it comes to what to wear with black ankle boots in winter – they really are made to go with everything! The juxtaposition of floral prints and more sturdy shoe boots works really well, even during the colder months. But you can also feel safe in the fact that pulling on your favourite black pair (either heels or flats) will work with skinny jeans and oversized jumpers at the weekend, shirts and dresses for the 9-5 (we love office ankle boots), and even that planned trip out for cocktails after work.

Victoria Beckham, Taylor Swift and Fearne Cotton wear ankle boots in autumn/winter

Photo Credit: Pinterest

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Spring/Summer Trends

When spring has sprung, there’s no need to worry about not being able to wear ankle boots. Trust us when we say that those boots you’ve come to live in will still have their place!

S/S Inspo: How to Wear Ankle Boots with Dresses

During the daytime, a dress with boots combination is both cute and comfortable. There are many pairs on the high street that incorporate sandal details such as sling backs, so that your feet aren’t so closed in. Summery outfits with brown boots look fab during the day, too – pair with a patterned spaghetti strap dress and denim jacket for a relaxed vibe, or high-waisted shorts and ankle boots when it’s hot.

We also love the floral embellished detailing on boots right now, which can be worn with a dress at any time of day and really suit the spring.

S/S Inspo: Evening Outfit with Boots

When it comes to how to wear ankle boots at night, heeled peep toes or pointed boots with shorts or skirts are a real winner, but also work if you want to be comfortable in your jeans and leather jacket. That’s the great thing about ankle boots – they can dress up or down any outfit choice. Plus the famously stylish mid-heel is sure to let you dance the night away (without the pain!).

If you can handle it, the heeled variety make a great mini skirt with ankle boots combo, as well as looking fab with a dress. And you definitely won’t need to question what to wear with black skinny jeans again – this is a perfect evening look.

S/S Inspo: Office Ankle Boots

If you thought that workwear could not include ankle boots during the summer, think again! A pencil skirt with boots can look so chic, particularly if you opt for a mid-heel to elongate the leg, but which also allows your feet enough comfort to get through a long day. Midi, floaty skirts are a must-have for warmer work days and look effortlessly stylish with boots.

Celebrities and bloggers wear ankle boots in spring/summer

Photo Credit: Pinterest

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Our Top 15 Ankle Boots

Our featured top 15 cover all seasons, styles and times of day, and each include something unique. The black leather boot is a wardrobe essential, but many brands are adding a hint of colour to the heel or subtle embroidery across the ankle. We love the burgundy heel from Oasis below, which will instantly glam up your look.

Alongside popular leather items, suede is still a big hit and we particularly love the autumnal reds, browns and greens available. The gorgeous deep blue colour on the Chloe ankle boots also looks incredibly luxurious, as does the detailed scalloped stitching across the front.

Our floral faves come from mom jeans and an oversized jumper during the day, as well as with your staple leather skirt during the evening. This can also be said for those killer leopard print boots!

There are different heel sizes to choose from within this selection, to suit all manner of activities. If you have a long day of retail therapy on the cards, you can’t go wrong with a classic pair of Chelsea boots, and if you’re after office ankle boots or you have another reason to dress up, the mid-heel will be perfect.

Have you got a favourite yet?

Anthropologie Tassel Boots
Anthropologie £82.95
ASOS Wide Fit Peep Toe Shoe Boots
ASOS £42
ASOS Chunky Ankle Boots
ASOS £35
ASOS Miss Selfridge Leopard Print Boots
ASOS £68
Dune Tan Warm Lined Chelsea Boots
Dune £85
Michael Kors Mercer Cutout Leather Ankle Boots
Michael Kors £195
Miss Selfridge Divine Burgundy Split Heel Boots
Miss Selfridge £27
Marks and Spencer Block Heel Western Trim Ankle Boots
Marks and Spencer £35
Net-a-Porter Chloe Suede Scalloped Ankle Boots
Net-a-Porter £600
New Look Black Suedette Double Strap Chunky Block Heels
New Look £13
Oasis Terri Ankle Boots
Oasis £45
Office Literally High Cut Boot Black Cherry Blossom Embroidery
Office £70
Office Bramble Chelsea Boots Black Leather
Office £70
Topshop Madame Embroidery Boots
Topshop £89
River Island - Buckle Shoeboot
River Island £38

Top Tips on How to Wear Ankle Boots All Year Round

  • Invest in a good quality pair of black ankle boots – they go with anything and everything so you’re bound to get enough wear out of them to justify the cost.
  • Peep toes and sandals are perfect for changing seasons and evening looks.
  • Contrasting floral prints with heavy duty boots really works – get styling!
  • Embroidery and velvet is so in right now. Why not be brave with pattern or fabric choice and let your feet do the talking?
  • Don’t worry about what to wear with brown boots – they definitely suit skirts and dresses at summer time.
  • High ankle boots work well with pencil skirts, particularly if you go for a mid to high heel.
  • When it comes to jeans and boots, tuck your skinnies in but roll up boyfriend jeans for a look that’s bang on trend.
  • Go for a chunky block heel for comfort during the day and night.
  • Don’t be afraid of colour, particularly if the rest of your outfit is more basic.
  • Ankle boots with frayed jeans look amazing- experiment with ankle socks and jean styles too.

It’s safe to say that the ankle boot obsession is here to stay and we couldn’t be happier. The variety of styles, colours and emerging patterns are bringing these trusty shoes up to date and making outfits more fun. Be bold with your choices as these styles weren’t just made for walking, but talking too!

Read more great articles on women’s fashion here at

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