I'll admit, I wasn't a fan of this pairing at the beginning, since I felt like it looked a little frumpy on me. But I've grown fond of it in recent months for the comfort factor alone. The sneakers part needs no explanation, and mid-calf-length skirts are arguably the coziest skirt length—you're not tripping over the hemline, as is often the case with a maxi skirt, nor are you constantly tugging it down, which tends to happen with a mini.
And from a fashion perspective, there's a lot to love about summer's hottest sartorial coupling. "The combination of sneakers and a midi skirt balances the masculine and feminine, and balance is an extremely important part of styling," says Nicole Pollard, Los Angeles-based personal stylist and founder of Lalaluxe. "It's classic without being boring, so it works for any age. Plus, there's beauty in comfort. When you feel comfortable you stand taller, move freer, and have that effortless vibe we all aspire for."
If, like me, you struggle to feel statuesque in a midi skirt and sneakers, Pollard has a few tips that'll help you pull it off. First, she says, experiment with different skirt lengths to find the one that best suits you. "For me, midi skirts look best below the widest part of my calf, but for others it can be just below the knee or just above the ankle," she says. She also recommends using color strategically if your outfit feels proportionally off. "I'm 5'4" and wear a size 10 shoe, so I'll pair a lighter skirt with dark sneakers to draw the attention upwards," she says.
But ultimately, anything goes with this look, so don't be afraid to do you. "You can take a slip dress and sneakers and pair it with a vintage army jacket for a day of flea market shopping—and then wear the same thing with a tuxedo jacket and brass clutch for a night out," Pollard says. "Simply put, it's a wardrobe staple." Here, we've sourced seven foolproof midi-and-sneaker combos that'll take you through Labor Day and beyond—and they'll make your last-minute packing game way less frenzied.
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