Not All Boots and Trousers Go Together, But This Combination is Perfect

As the weather starts to turn and the cold creeps in, ankle boots become an undisputed essential. The beauty in this perennial staple? The right pair goes with absolutely everything. Whether you're a midi dress obsessive or a fan of the classic jeans-and-a-tee formula, you'll soon find yourself reaching for your Chelsea, heeled or lug-soled boots on an almost-daily basis. 

There's a specific combination we've been spotting lately that we decided was worth drawing your attention to: cropped trousers and ankle boots. The former is a popular style during the spring and summer months, when we want to have as much skin as possible on show. But it turns out cropped trousers can work wonderfully in autumn, and arguably look even better with ankle boots than full-length trousers. Think about it; the higher the hemline, the more boot is visible.

The proof is in the following looks we've saved from Instagram, featuring ankle-length trousers, jeans and culottes and their perfect boot pairing. You know what to do.

1. Slim-Fit Jeans + Lace-Up Boots


(Image credit: @livpurvis)

Style Notes: Team slim-fitting jeans with boots that lace up tight to the ankle—this will have an elongating effect and prevent the boots from being swamped.

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2. Straight-Leg Trousers + Chelsea Boots


(Image credit: @madeleinebuggekarlsen)

Style Notes: Create a laid-back weekend look with relaxed black trousers and a comfy pair of Chelsea boots. Tip: try to have the hemline graze the top of the boot or overlap slightly. This looks a lot sleeker than having an inch of calf on show.

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3. Wide-Leg Trousers + Pointed Boots


(Image credit: @lefevrediary)

Style Notes: Cropped wide-leg trousers or culottes look best with narrower boots, ideally featuring a thin heel and pointed toe to balance out the silhouette.

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4. Ribbed Trousers + Chunky Boot


(Image credit: @charlottekuhrt)

Style Notes: You might be used to wearing your ribbed lounge-bottoms with slippers, but try styling them with chunky boots for a cool weekend look. 

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5. Straight-Leg Jeans + Heeled Boots


(Image credit: @_jessicaskye)

Style Notes: You'll often find us lauding the versatility of straight-leg jeans, so it should come as no surprise that the cropped kind is just as easy to style. We're wearing ours with heeled ankle boots like Jessica Skye.

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Next Up: 6 Rules French Women Always Follow When Styling Wide-Leg Trousers

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.