5 Ways to Wear Ankle Boots, According to Instagram's Best Dressed

Ahh, ankle boots, that perennially stylish wardrobe staple that you return to time and time again whenever the temperature outside starts to drop. This year, I impatiently counted down to my favourite season of the year (boots season) and was not disappointed by the vast array of new boot trends popping up on the runways and on my social feed. But as usual, it was the trusty ankle boot that were the first ones I reached for this season.

No matter your age, style or shoe preference, ankle boots are all-rounders. Dressing up? Add stiletto-heel ankle boots. Running errands? That's a white tee, jeans and sturdy ankle boots kind of day. Heading into the office? I've got you, it's all about the cashmere knit, satin skirt and leather ankle boots. But much as we love our timeless ankle-hugging friends, it can be challenging to come up with fresh, innovative ways to style them. That is, until now. 

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(Image credit: @astyleedit)

In a bid to find the chicest way to wear our favourite boots of all time, I scoured the feeds of editors, tastemakers and the street style set to find the looks that give the footwear staple a new lease of life, particularly for autumn and winter. And I think you'll be very pleased with the results. Keeping scrolling to see five new ways to wear ankle boots for autumn/winter and shop the best looks now.

1. ANKLE BOOTS + SHEARLING JACKET + STRAIGHT-LEG DENIM

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(Image credit: @emmanuellek_)

Style Notes: For cosy weekends and casual weekdays, look no further than a shearling aviator. There are exceptional styles on the market now for every possible budget, just be sure to buy one size up for a slouchy effect (and to leave enough room for a chunky knit when needed). 

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2. ANKLE BOOTS + DOUBLE DENIM 

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(Image credit: @smythsisters)

Style Notes: Yes, double denim is a retro look, but I mean that in the best possible way. This easy outfit takes five minutes to throw on but looks effortlessly polished. As soon as the cold snap hits, just add a turtleneck underneath, and a longline coat on top. 

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3. ANKLE BOOTS + AN LBD

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(Image credit: @rayan.xasan)

Style Notes: I'm bored of strappy sandals for the evening—give me boots I can last all night in. Rayan proves that all you need to make simple boots feel dressier is, well, a dress. And a long black dress will work for any event on your calendar. 

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4. ANKLE BOOTS + A MAXI COAT + AN OVERSIZED SHIRT

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(Image credit: @anoukvye)

Style Notes: If a long coat and boots isn't the perfect combination for autumn and winter, I don't know what is. Break up a dark outfit with clean, white accents like an oversized shirt and jeans and you've got yourself a new, easy work uniform. 

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5. PRINTED ANKLE BOOTS + EVENING TOP + BLACK TROUSERS

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(Image credit: @lucywilliams02_ )

Style Notes: Maximalist dressers, this one is for you. A good pair of ankle boots don't have to be plain black leather—you can stand out from the crowd in patterned, coloured and textured boots too. The best way to make the most of your new boots? Add a little sparkle for eveningwear and opt for cropped trousers that show your boots in all their glory. 

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Up Next: 8 Simple But Incredibly Chic Ways to Style a Black Blazer This Season

This story was originally published at an earlier date and has since been updated.

Fashion Editor

Remy Farrell is a London-based shopping editor with nearly 10 years of editorial experience covering fashion, beauty and lifestyle. After graduating with a journalism degree and working on the editorial and fashion teams for titles such as Grazia, Elle, Cosmopolitan and British Vogue, she moved into the luxury e-commerce sector, working as fashion assistant at TheOutnet.com styling for the social media channels and helping to develop the collections for the in-house brand Iris & Ink. After expanding an assisting and styling portfolio that includes shooting talent such as Gigi Hadid, Victoria Beckham and Miquita Oliver, she also branched out into beauty, creating tried-and-tested reviews and diverse beauty content.

In her role as shopping editor at Who What Wear, Remy is interested in discovering new and exciting brands to share with the Who What Wear readership and particularly loves uncovering hidden gems at affordable prices to make shopping accessible to everyone.

Born and raised in Sheffield, Yorkshire, Remy moved to London in 2014 and lives in the Docklands with her partner and pug Billie.