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 Jeans
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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This look so much more expensive than it is.
Albaray is one of my favourite brands for denim.
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 such a good investment piece.
3. Ankle Boots + Classic 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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This is such a timeless, classic style.
I love the thin heel, it feels so sophisticated.
A letter pendant necklace is part of my everyday look.
4. Ankle Boots + Maxi Coat + 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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I can't believe this is from the high-street.
WNU is every fashion editor's go-to for shirts.
I love the contrast between the suede and leather.
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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This asymmetric top with it's slightly shimmery finish is perfect for a night out.
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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The subtle pinstripe is so chic.
A matching tailored set makes you feel instantly put together.
Pointed-toe boots are such a classic style.
7. Ankle Boots + Column Skirt + Shirt
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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An Oxford shirt is such a classic.
The kind of skirt that can be styled for so many occasions.
For just the right amount of height.
8. Ankle Boots + Oversized Blazer + Barrel-Leg Jeans
Style Notes: Liv's ensemble is an combo I reach for time and time again when it comes to autumn. Flat chunky boots are so classic and work perfectly paired with an oversized blazer and barrel-leg jeans. On those colder days, you can easily swap the vest top for a chunky knit.
I'd size up by two or three sizes to achieve that oversized finish.
I'm obsessed with barrel-leg jeans at the moment.
One of The Row's iconic styles.
9. Ankle Boots + Funnel Neck Jacket + Jeans
Style Notes: Funnel-necks are making their comeback and judging by this jacket, we can totally see why. Paired with blue jeans and ankle boots, it's such an effortlessly cool outfit and one you'd wear on repeat.
This Massimo Dutti jacket went viral and has already been restocked once.
Agolde is one of my go-to brands when I want to invest in a new pair of jeans.
So chic.
This story was originally published at an earlier date and has since been updated.