These 8 Ankle-Boot Outfits Are So Good You'll Want to Live in Them This Autumn

We know you're probably making the most of the last few weeks of sandal weather, but now that we're experiencing the first signs of autumn, it's a good time to start thinking about clothes and shoes to wear in the colder weather. And where better to start than ankle boots

Ankle boots are a trusty accessory that'll easily transition you into autumn. So much so they're usually the first thing we'll start wearing once the temperature drops, with the best styles always selling out early. However, assuming you already own a pair of ankle boots that you love, we've instead focused our efforts on unearthing some excellent ankle-boot outfits to wear them with.

Styling up ankle boots is easier than it sounds. You need to take into account the silhouette and length of your clothing to ensure it doesn't throw off the overall aesthetic of your look. To help you master the art of creating chic ankle-boot outfits, we've rounded up some impressive looks for you to try. 

From prolonging the lifespan of a summer dress to navigating the tricky leather-on-leather situation, here are eight ways to style your ankle boots this autumn.

1. LIGHT-WASH DENIM + BRIGHT BAG + BLACK BOOTS

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(Image credit: @meganadelaide)

Style Notes: For a '90s take, try wearing light-denim jeans and jumpsuits with a pair of black ankle boots—the contrast feels very of the decade and will look the cool throwback part. 

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2. BLAZER + MINIDRESS + SOCK BOOTS

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(Image credit: @champagnemani)

Style Notes: One of the easiest ways to make your minidresses feel effortless is to sling a blazer over the top and finish with a pair of boots. We always opt for fitted sock styles, as they fit to the natural line of your leg. 

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3. BELTED JACKET + FLUID SKIRT + SQUARE-TOE BOOTS

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(Image credit: @hannasteffanson)

Style Notes: Belted outerwear is fast becoming one of the biggest jacket trends of the season. Paired with a floaty skirt and trusty ankle boots, this is an outfit you'll want to wear on repeat this autumn. 

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4. SHACKET + ERCU JEANS + HEELED BOOTS

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(Image credit: @hannahlewisstylist)

Style Notes: We're sure you'll be pleased to hear that shackets are still going strong for 2021. We love how Hannah has given hers autumnal appeal with on-trend, loose-fit jeans and a pair of heeled ankle boots.

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5. JUMPER DRESS + TOP-HANDLE BAG + CHUNKY FLATS

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(Image credit: @slipintostyle)

Style Notes: Jumper dresses are synonymous with autumn dressing and, naturally, look their best paired with ankle boots. While they can be dressed up with a heeled style, we love how they look when paired with chunky, track-sole boots. 

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6. TRENCH COAT + PATTERNED TROUSERS + WESTERN BOOTS

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(Image credit: @the_oluwaseun)

Style Notes: As far as 2021 autumn outfits go, this one is perfection. A trench coat paired with tartan trousers and Western boots? Inspired. 

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7. LEATHER JACKET + SUEDE SKIRT + SUEDE BOOTS

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(Image credit: @alexachung)

Style Notes: We're often asked if leather textures work together, to which we say yes—as long as you add some suede into the mix to soften things up. Alexa Chung's combination of a leather jacket, suede skirt, and suede boots is a perfect example of what we mean. 

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8. SHIRT DRESS + JAZZY BAG + PATENT BOOTS

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(Image credit: @ada_oguntodu)

Style Notes: You needn't pack away your summer dresses just yet. Style them with a pair of ankle boots (a patent finish always feels autumnal), and you'll get at least a month's more wear out of them. 

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Next Up: 5 Autumn Boot Trends an Expert Thinks You Need to Know About

Maxine Eggenberger
Deputy Editor

Maxine Eggenberger is Who What Wear UK’s deputy editor and has over twelve years of experience in fashion journalism. She been creating engaging and elevated style content for Who What Wear UK since 2018, covering runway reports, emerging trends, long-form features, self-styled shopping stories, and columns, including her edit of the best new-in buys. She ensures the highest editorial standards are met across the site, works closely with influencer talent on content initiatives, represents the brand at industry events, and regularly contributes to social media. Previously, Maxine appeared on TV in her own fashion segment and has interviewed countless celebrities—everyone from Victoria Beckham to Oscar winner Lupita Nyong’o. 


Prior to Who What Wear UK, Maxine’s career began when, after completing her first-ever internship, she was offered a position on the Look magazine fashion desk. She accepted, leaving university a year early in the process. She went on to become the title's fashion news and commercial content editor, with a stint as InStyle.co.uk’s fashion writer along the way. She later served as Look’s acting Editor in Chief before embarking on a successful freelance career, working with Grazia, The Pool, and Marie Claire amongst others. Maxine works remotely from her countryside home near Edinburgh.