It's True That Not All Skirt-and-Boot Pairings Work, But These 8 Definitely Do

At this time of year, skirt trends step into the spotlight. Whether you lean towards the knitted, silky or mini variety, there's no doubt that this chic choice of bottoms is endlessly versatile and transitional-weather appropriate.

Ankle boots sit right up there with skirts on the top tier of autumn essentials. So it makes sense that we would style these two hero items together. Certain outfit formulas work every time, but landing on the right combinations is often a process of trial and error. Luckily, we've consulted the It girls of Instagram to teach us a few lessons in pairing ankle boots with skirts so you can skip ahead to the good part: wearing your winning look.

Scroll on to find out which shape to team with that liquid-looking midi you've been reaching for or the silhouette that works best with a mini. These five effortless outfits sure show us how it's done.

8 STYLISH WAYS TO WEAR ANKLE BOOTS WITH SKIRTS THIS WINTER:

1. Satin Skirt + Blazer + Heeled Boots

Brown satin skirt with black blazer and heeled boots

(Image credit: @thecarolinelin)

Style Notes: Whilst brown and black are typically worn separately, these two neutrals actually look incredibly sophisticated when worn together. Learn from Caroline's expert outfit pairing and try styling a satin brown skirt with a black blazer and heeled boots.

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2. Leather Skirt + Suede Boots

Rebekah in black leather skirt with red bag

(Image credit: @iamnkirote)

Style Notes: Whether you chose leather or pleather, you can't deny how chic an A-line maxi skirt in this material paired with suede boots looks. When you're working with a monochrome black outfit, learn from Rebekah Nkirote and add a pop of colour with the help of a bag.

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3. Pleated Midi + Square-Toe Boots

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(Image credit: @venswifestyle)

Style Notes: How to update that pleated midi skirt you 100% have lurking in your closet? Simply add a slick pair of Western boots.

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4. Lug-Soled Boots + Monochrome Co-ord

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(Image credit: @daniellejinadu)

Style Notes: Make like Danielle and pair a refined all-white outfit with chunky boots. A patent leather always stands out, especially when you have monochrome everywhere else.

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5. Western Boots + Midi Skirt + Frilly Blouse

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(Image credit: @frannfyne)

Style Notes: If you're interested in another gorgeous cream-coloured look, try mixing cowboy boots and silky fabrics for a match made in fashion heaven. There's something about the rawness of a Western style that contrasts dreamily with a fluid, feminine skirt, as Franny shows here.

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6. Cargo Skirt + Crocodile-Inspired Boots

Sabina in green cargo skirt with croc texture boots

(Image credit: @sabinasocol)

Style Notes: Cargo trousers have been in high demand this year. Now that autumn has rolled around — and thus, skirt season — why not swap out your favourite pair for a skirt in the same material? Sabina Socol expertly pairs hers with a long-sleeve top and crocodile-print boots for a tonal look.

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7. Striped Jumper + Leather Mini Skirt + Zip-Front Boots

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(Image credit: @francescasaffari)

Style Notes: Counterbalance the mini skirt with a chunky boot. The Row are renowned for its boots, of course!

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8. Shearling Gilet + Black Denim Skirt + Chelsea Boots

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(Image credit: @bubblyaquarius)

Style Notes: Girls about town, take note. While this outfit is polished, you won't feel restricted as you work your way through your to-do list. Sounds like the best of both worlds to me.

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This piece was published at an earlier date and has since been updated.

Freelance Fashion Editor

Bébhinn Campbell is an Edinburgh-based fashion and lifestyle writer and editor. She started her first blog at age 14 and went on to intern at print and digital publications in Berlin and London, including Dazed & Confused and Indie magazine.

A job at a fashion startup took Bébhinn from Ireland to Scotland in 2019, where she now works as a freelance journalist and copywriter covering everything from travel and interiors to styling advice. As a contributor to Who What Wear, Bébhinn always keeps her eyes peeled for emerging trends and looks worth writing about. She prides herself on her ability to cut through the noise and identify solid investment buys, exciting new brands and fresh takes on classic design.

In her spare time, Bébhinn enjoys perusing Edinburgh’s best vintage shops, working through her out-of-control book collection and watching dog reels on Instagram.