Not All Shoes Go With Flared Leggings—These 6 Styles Do

Flared leggings are a fashion paradox. On one hand, they're extremely easy to step into and wear as you go about your day, particularly when working from home or running errands. But once you attempt to style them with any piece that brings some polish or pizazz, you're met with a harsh reality: This wardrobe staple is actually quite tricky to style.

But trust me—your future self will thank you for figuring it out. Depending on how extreme the flare is and how much you want it to define the look, focus on getting the proportions right first. If you don't want to wear a form-fitting top half, an oversized t-shirt or shirt will complete the comfy ensemble. I'd suggest one of the striped variety for the season ahead. However, if you're to show off your waistline, don a boxy cropped blouse or tee with your versatile bottoms.

@cassklatzkow wearing split-hem leggings with trainers and blazer

(Image credit: @cassklatzkow)

At this point, I'm sure you’re wondering which shoes to wear. This is arguably the most important and principally challenging aspect of building an outfit around flared leggings. You want your chosen soles to pull the ensemble together and make it ready for the outside world without sacrificing comfortability. (That’s why you for leggings in the first place, right?)

Eager to decipher which shoes to wear with flared leggings, I took my time browsing the internet and taking inspiration from celebrities and influencers I've spotted wearing the rising trend. In no time, a few chic options stood out. From square-toe boots to the French footwear that keeps on giving, these winning shoes make total sense. Scroll down to see which fashionable footwear made the cut.

1. CHUNKY LOAFERS

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(Image credit: @alicezielasko)

Style Notes: A bulkier shoe will balance out the legging's slim silhouette, especially when paired with an oversized blazer or knit.

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2. POINTED BOOTS

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(Image credit: @ali_tate_cutler)

Style Notes: A pointed shoe has the potential to elevate this casual style and will also elongate your legs, particularly if you opt for a monochrome shoe-legging combination like Ali Cutler has.

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3. BALLET FLATS

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(Image credit: @helenacuesta)

Style Notes: Ballet flats are this year's rediscovered gem. The fashion set has realised they go with just about everything, flared leggings included.

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4. CLASSIC TRAINERS

@amaka.hamelijnck wearing trainers with grey leggings and top

(Image credit: @amaka.hamelijnck)

Style Notes: Put comfort first, and sport a fail-safe sneaker with your flared leggings, whether thats a simple pair of Converse or New Balance treads.

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5. SQUARE-TOE BOOTS

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(Image credit: @stephaniebroek)

Style Notes: Toughen up your leggings with a thick-soled, square-toed boot. Cool girl Stephanie Broek demonstrates the effect, lifting her monochrome outfit with a bubblegum-pink bag.

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6. HEELED MULES

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(Image credit: @millakuoksa)

Style Notes: On sunny afternoons and late nights on the town, minimalistic mules promise to make your leggings going-out appropriate.

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This piece was originally 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.