It says something about the state of fashion today that women who can afford, or get gifted, any fresh-off-the-runway finery they desire—models, pop stars, even some fashion editors—choose to kick around in sweatshirts, track pants, and sneakers. But while it may appear unstudied, the slouchy, sporty look seen lately on influencers like Rihanna Cara Delevingne, and models Lexi Boling and Binx Walton is anything but lowbrow. Look closely, and an ostensibly casual Baja East sweatshirt turns out to be double-faced cashmere; Hood by Air’s discreet leather backpack features an elaborate attached hood and a $1500 price tag. And Celine’s high-end skater shoes—like Vans but rendered in python—have supplanted the stiletto as the front-row footwear of choice for harried editors dashing between shows.