As soon as the temperatures drop and the rain inevitably arrives, one footwear style leaps up our list of must-haves: boots. This season, knee-high styles have been dominating the conversation, but personally, I'm loyal to the ankle boot. Versatile, comfortable and understatedly chic, the ankle boot has my vote for most essential autumn footwear.
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. 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, 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 seven new ways to wear ankle boots for autumn/winter and shop the best looks now.
HOW TO WEAR ANKLE BOOTS, ACCORDING TO INSTAGRAM BEST DRESSED:
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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I'm obsessed with this dark chocolate colour.
The perfect pair of straight-leg jeans.
Brown ankle boots are so versatile. Wear with jeans, dresses and skirts.
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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This denim jacket will work hard in your wardrobe year-round.
Don't forget the matching jeans.
These pointed-toe ankle boots are so chic, and I love the contrast of the suede with the denim.
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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I'm always a fan of COS' take on a black dress.
Influencers, celebs and editors all love these boots.
The easiest way to add a Parisian touch to any look.
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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A wardrobe staple you'll reach for time and time again.
The whole Who What Wear team loves Aligne's outerwear offering this season.
Ecru jeans look so good in winter when paired with cosy knits or layers.
Opt for these is you want to give a subtle nod to cowboy boots.
5. PRINTED ANKLE BOOTS + EVENING TOP + BLACK TROUSERS
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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A metallic knit is winter's answer to the jeans-and–a-nice-top look.
I love these comfy yet chic trousers. Wear with shirts, blazers and knitwear.
A patterned pair of boots add a playful touch to an evening look.
6. ANKLE BOOTS + TAILORED SET
Style Notes: I'll always be a fan of a tailored set with a white t-shirt as an easy yet elegant look. While I typically style them with trainers to keep the ensemble casual, I think ankle boots are a brilliant substitute to elevate the look just enough without making it look ultra-formal.
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Aligne has developed a cult following for its chic tailored separates.
A crisp white t-shirt is a layering essential.
The tailored trouser our editors swear by.
Pointed-toe boots may be trending this season, but a square-toe Chelsea boot is an undeniable classic.
A modern take on the quiet luxury trend.
7. COLUMN SKIRT + SHIRT + POINTED-TOE ANKLE BOOTS
Style Notes: When it comes to skirts, column styles remain at the top of my favourites list—and Francesca's outfit is a perfect demonstration of why. Sleek, understatedly cool and infused with a French vibe I can't resist, this whole outfit is an autumn dream.
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Classic in name, classic in style.
The kind of skirt that can be styled for so many occasions.
I love how Francesca uses a studded belt to give the outfit a bit of edge.
For just the right amount of height.
This story was originally published at an earlier date and has since been updated.