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

There’s a paradox around flared leggings—on the one hand, they’re extremely easy to step into and go about your day, particularly when working from home or running errands. Yet once you attempt to style them with any kind of polish or pizazz, you’re met with the harsh reality: this wardrobe staple is actually quite tricky to wear.

But trust me, your future comfort-seeking 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’re a little self-conscious about the form-fittedness of the top half, an oversized jumper will complete the comfy ensemble. I’d suggest one of the striped variety for the season ahead. Keen to show off your waistline? Don a boxy cropped blouse or tee with your versatile bottoms.

At this point, I’m sure you’re wondering “But what about the shoes?” Yes—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 outside world-ready, without sacrificing the snugness that’s motivated you to opt for leggings in the first place.  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 in 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.

A bulkier shoe will balance out the legging’s slimline silhouette, especially when paired with an oversized blazer or knit.

For working out, or not.

This versatile design will also suit dresses, straight-leg jeans, tailored sets—you name it.

A great footwear option for the office.

This subtle lug sole adds just enough edge.

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

Sleek, stretchy and irresistiblycomfortable.

There’s something so polished about a white boot.

Create an all-black look with this premium pair.

Arket’s accessories could easily be mistaken as designer.

Ballet flats are this year’s rediscovered gem; the fashion set has realised they go with just about everything. Flared leggings included.

An elegant alternative to black leggings.

That colour though.

Prepare to go everywhere in these timeless flats.

You could assemble some fun looks with this pump.

Put comfort first and sport a fail-safe sneaker with your wide-leg bottom, whether simple Converse or a pair of Veja treads is your idea of classic.

Show off your shoes with that trendy split hem.

Converse, but make them fancy.

H&M nails basics every time.

These will fast become your most-worn trainers.

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.

These wear-all-day bottoms will work whatever the season.

Chelsea boots take top prize for the most wearable winter footwear.

The extreme angled heel and sharp square toe make these feel so expensive.

The dreamiest green.

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

Keep it simple with an ultra-comfy design.

Take your ensemble from day to night with this evening mule.

For the playful dressers among us.

Part loafer, part mule.

Next Up: The 9 New-In Pieces I’m Adding to My Wish List This Week

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