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 shirt or jumper 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.
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.
The Best Shoes to Wear With Flared Leggings:
1. CHUNKY LOAFERS
Style Notes: A bulkier shoe will balance out the legging's slim silhouette, especially when paired with an oversized blazer or knit.
Shop the Look:
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.
Just enough heel.
2. POINTED BOOTS
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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Sleek, stretchy and irresistibly comfortable.
There's something so polished about a black ankle boot.
Suede is so elevated.
Create an all-black look with this premium pair.
3. BALLET FLATS
Style Notes: Ballet flats are this year's rediscovered gem. The fashion set has realised they go with just about everything, flared leggings included.
Shop the Look:
An elegant alternative to black leggings.
Classic.
You could assemble some really chic looks with this pump.
Mesh flats are so on trend.
4. CLASSIC TRAINERS
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.
Shop the Look:
Opt for a pair with a trendy fold-waist detail.
Converse are so classic.
New Balance dad sneakers continue to be a top style.
These will fast become your most worn trainers.
5. SQUARE-TOE BOOTS
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.
Shop the Look:
These wear-all-day bottoms will work whatever the season.
Sock boots take top prize for the most comfortable footwear.
I love the buckle detail.
The dreamiest shade and shape.
6. HEELED MULES
Style Notes: On sunny afternoons and late nights on the town, minimalistic mules promise to make your leggings going-out appropriate.
Shop the Look:
Keep it simple with an ultra-comfy design.
Take your ensemble from day to night with this evening mule.
Such an easy, everyday mule.
Perfect for injecting a dose of colour.
This piece was originally published at an earlier date and has since been updated.
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