The Chicest Shoe Trends to Wear With Leggings, Jeans, and Skirts

While we’re always down for surprising and statement shoe styles for special occasions, it’s those more versatile silhouettes that are of utmost interest for day-to-day life. Although, we totally understand that your footwear selection of choice these days is likely a fresh pair of tube socks to stay comfy at home with the current situation. Well, if you are interested in shoe shopping or want a bit of shoe inspiration to bookmark now and note for later, we wanted to take the next few moments to cover some of the top shoe trends of the moment.

With versatility top of mind, the three silhouettes in question are particularly noteworthy because they team flawlessly with anything, including common staples like leggings, jeans, and skirts. To highlight further, we’re showcasing past imagery of how fashion girls have worn the chicest shoe trends right now with all three of the essentials above—complete with some shopping picks on how to get each look, too.

Black Mules

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(Image credit: @ileniatoma_)

While a more laid-back shoe choice might come to mind first when thinking about a legging ensemble, a sleek pair of pointed black mules elevates the pant style even more, like in this 'fit featuring the leather jacket and cool accessories. 

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(Image credit: @sylviemus_)

A tube top is particularly trendy with jeans and polished mules.

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(Image credit: @carodaur)

Tie-up mules are forward and elevated with a printed silk skirt and a chunky knit. 

Sporty Sandals

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(Image credit: @itsmekellieb)

Featuring Velcro straps and sporty materials, these of-the-moment sporty sandals are an ideal match with a cool legging ensemble.

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(Image credit: @greceghanem)

Embrace a pastel or white sandal silhouette with a pretty monochromatic look.

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(Image credit: @gosiaboy)

Adding socks to these sandals feels just right paired with a sleek leather skirt.

Retro Sneakers

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(Image credit: @honeybelleworld)

Throwback sneakers are basically everywhere right now and will make anything you're wearing feel quite current. Case in point? This sweater-and-legging combo.

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(Image credit: @fakerstrom)

Wider-leg, light-wash jeans are where it's at with these retro sneakers. 

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(Image credit: @camillecharriere)

Go for a full-on sporty look by taking a note from this outfit with the pleated skirt, pullover, and trusty sneakers.

Next, check out more comfortable shoe trends worth trying.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retialers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.