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.
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.
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).
As you may or may not know, Mango’s shearling jackets are second to none this season.
The perfect dark-wash denim.
Brown ankle boots are so versatile. Wear with jeans, dresses and skirts.
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.
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.
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.
We’ll always love a minidress, but right now, it is the midis that have our hearts. I love the leg-split detail on this knitted style.
Influencers, celebs and editors all love these boots.
The easiest way to add a Parisian touch to any look.
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.
A wardrobe staple you’ll reach for time and time again.
The whole Who What Wear team loves & Other Stories’ 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.
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.
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.
