Not All Skirt-and-Boot Pairings Work, But These 5 Definitely Do

At this time of year, skirts are a hard-and-fast staple. 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.

1. Pleated Midi + Cowboy 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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2. 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.

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3. Western Boots + Midi Skirt

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(Image credit: @frannfyne)

Style Notes: Cowboy boots and silky fabrics are a match made in fashion heaven. There's something about the rawness of a Western style that contrasts dreamily with a fluid, feminine skirt.

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4. 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 renown for its boots, of course!

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5. 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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Next Up, I'm a Stylist - My Wardrobe Wouldn't Function Without This Simple Piece

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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.