I'm a Die-Hard Sneakers Gal—I Always Wear These 5 Skirts With Them

We love sneakers, plain and simple. So we're glad it's now acceptable to wear them just about anywhere (rather than just at the gym). The latest item we're seeing this street-style staple paired with? A skirt. It's the ultimate sporty-chic look, and you can bet we'll be copying it all season long.
See our favorite skirt-and-sneaker outfits ahead. But beware, they might convince you to trade your flats for trainers. From looks that pair classic Converse sneakers with denim to one that combines the "ugly" sneaker trend with cargo pockets, these are the ensembles we're taking note of. Thank us later!
Denim Skirts
We're team denim skirt all the way. While maxi hemlines and '70s-inspired garments are making a comeback in the form of long denim skirts, most fashion people still wear them with sneakers for a quick, on-the-go look.
Miniskirts
The shorter the skirt, the more fun. While micro miniskirts may be on their way out, pairing a skirt that hits mid-thigh with a pair of classic trainers is still a no-brainer. As the weather warms up, you'll spot fashion people embracing this look more and more.
Maxi Skirts
Those in favor of maxi skirts paired with retro sneakers, say aye! This combination is a favorite among editors and influences alike. Pair a neutral-colored skirt with a bright shoe to add dimension and color-blocking to your spring 'fit.
Sporty Skirts
If you're looking for an athletic-inspired combo, look no further than technical sportswear. With retro silhouettes and thick vintage lines, most sporty skirts are just as stylish as they are comfortable—especially when worn with an elevated pair of running shoes.
Cargo Skirts
Cargo skirts are still very much "that skirt," thanks to their massive popularity late last year. Since they were first introduced during the resurgence of the maxi hemline, fashion people have worn this style with toned-down lifestyle sneakers for a functional, technical look.
Next: 9 Major Shoe Trends That Will Be Everywhere This Spring

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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