5 Ways to Wear Ankle Boots, According to Instagram's Best Dressed (2024)

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 ofnew 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 Ireached 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 aboutthe cashmere knit, satin skirt andleather 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.

In a bid to find the chicest way to wear our favourite boots of all time, Iscoured the feeds ofeditors, tastemakers andthe street style set to findthelooksthatgive the footwear staplea 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 newways to wear ankle boots for autumn/winter and shop thebest looksnow.

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

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

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

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

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 + BLACKTROUSERS

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.