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Hailey Bieber -

How to turn a short summer outfit into fall-ready wardrobe? Add a blazer and chunky boots. Admittedly, it helps if you are a model married to a megastar, but mere mortals could make this work with a tee instead of the teeny top.

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Kourtney Kardashian and Addison Rae -

No, you don't have double vision! Gal pals Kourtney Kardashian and Addison Rae put in the leg work to show that chunky ankle boots can work with a tiny belted wrap dress.

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Kylie Minogue -

Kylie Minogue shows how to work the white ankle boots that have recently made a return to high-street style. Team with a long, sleek dress for impact, and a casual jacket to dress it down for post-work drinks.

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Rihanna -

Some celebs are known for embracing double denim, but how about triple denim? Rihanna shows how it's done, with a denim dress, jeans, and ankle boots.

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Zoë Kravitz -

Actress Zoë Kravitz frequently crops up on best-dressed lists, and her style is no flash in the pan. The star was rocking this timeless layered fall look with classic black ankle boots back in 2015.

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Khloé Kardashian -

Khloé Kardashian is another stylish star showing the enduring appeal of ankle boots. This 2016 look saw her pair fall-fabulous fawn and brown shades with ripped skinny jeans. The boots and bag combo is a winning detail.

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Katie Holmes -

A pandemic mask can't hide Katie Holmes' star status. Here, the actress shows how to do cozy-chic in style by teaming a warm jacket with mid-calf jeans and flat black ankle boots.

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Alexa Chung -

If anyone can pull off this outfit, it's Alexa Chung. The model and TV presenter wore this chunky-boot-and-dress combo to London Fashion Week in September 2021, but non-celebs could make it work with a less 'complicated' dress.

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Taylor Swift -

Another star with legs for days, talented Taylor Swift worked white, lace-up stiletto boots into a classy monochrome look for the 2020 NME Awards in London.

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Kate Middleton -

Catherine, Duchess of Cambridge may hold a royal title, but she's known for embracing high-street fashion. This classic dress, opaque tights, and buckled black ankle boots outfit could easily work as a desk-to-drinks look for fall.

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Jennifer Lopez -

All eyes were on J-Lo when she wore this chic, fall-friendly look. She teamed pale gray buckled boots with casual-chic pants, a blazer jacket, and designer bag and shades to seal the A-list look.

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Selena Gomez -

The singer and actress looks fall-cozy in this sweet look. A warm faux-fur, opaque tights, and tan Chelsea boots make it a workable look for any girl about town.

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Heidi Klum -

Heidi Klum literally has "'90s supermodel" written all over her in this photo, and she shows she still cuts it in the style stakes with her skinny jeans and low-rise ankle boots combo.

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Jennifer Aniston -

Jennifer Aniston shows her style credentials in this classic skinny-jeans-and-ankle-boots look. Grab a matching black jacket and top, and you're good to go.

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Courtney Cox -

Not to be outdone, Aniston's 'Friends' co-star Courtney Cox works the all-black look with a pair of stylish-yet-sensible flats.

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Kate Hudson -

Don't be afraid to mix your colors! Kate Hudson shows how to pair blue denim with red boots and a fawn coat as she braves the rain in New York City.

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Gigi Hadid -

The younger generation of fashion icons love an ankle boot, too. Model Gigi Hadid wears a low-heel and loose-fitting pants to make this a look that's practical for those who have to get around on foot.

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Zendaya -

Fashion favorite Zendaya never puts a foot wrong when it comes to style. Follow her lead and go for a silky dress, black tights, and ankle boot combo. The calf-length coat makes this warm enough for fall nights out.

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Kendall Jenner -

The Carrie Bradshaw vibes were strong when Kendall Jenner walked the runway for the Giambattista Valli Loves H&M show in October 2019. Pairing red ankle boots gives the uber-feminine dress a punkier edge.

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Sarah Jessica Parker -

Speaking of Carrie Bradshaw, Sarah Jessica Parker absolutely kills a pair of silver, heeled ankle boots amid a sea of stiletto shoes. The loose jeans and casual sweater make this a strong look for daytime shopping sprees.

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Harry Styles -

Men can wear ankle boots with flair, too! Harry Styles is a renowned wearer of the style, and the fresh-faced singer rocked his Cuban heels with pride at the British Fashion Awards back in 2014.

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Cindy Crawford -

Supermodels never lose their style! Cindy Crawford looks chic from head to toe with a fall look combining fawn boots, coat, and bag with classic blue jeans.

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Paris Hilton -

Paris Hilton works her denim-and-ankle boots to perfection, too. The bold top and signature giant shades make this a look that could work equally well for lunch dates or an evening out.

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Claudia Schiffer -

Classic chic from supermodel Claudia Schiffer, whose comfy-looking flat boots work perfectly with tight-fitting blue jeans.

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Meghan Markle -

Another star who looks great in the all-black look, Meghan Markle goes for tailored black pants over her chunky-heeled black ankle boots.

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Sandra Bullock -

Sandra Bullock looks fiercely fashionable in this look, which pairs fitted black pants with a killer-heeled boot and eye-catching faux-fur coat.

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Kate Moss -

Kate Moss has been a style icon for decades, but you don't have to be a supermodel to work this simple-but-chic look. A well-fitted black dress, sharp ankle boots, and oversized black bag look good for pretty much any occasion.

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Victoria Beckham -

Singer-turned-fashion designer Victoria Beckham has always been known for her pared down, elegant looks, and she looks runway perfect in a black mini with classic black ankle boots.

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Jordyn Woods -

Model Jordyn Woods can work a white ankle boot with flair. This club-ready dress and ankle boot combo is an easy-to-copy look that could set any dance floor on fire.

Sources: (The Zoe Report) 

See also: The pantsuit revolution and the women that wear them

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