As a streetwear label “by girls, for girls,” MadeMe made headlines last year for its collaborative revamp of X-Girl , the beloved alternative ’90s label. The campaign images featured Coco Gordon Moore , the daughter of X-Girl creator and Sonic Youth singer Kim Gordon. To celebrate this season’s collection, MadeMe founder Erin Magee looked for a face that would evoke the attitude of both female-centric labels—and Lourdes “Lola” Leon, Madonna ’s daughter and the second campaign’s star, had been on her mind for quite a while. The 20-year-old possesses a ’90s-minded style that fits well with the MadeMe and X-Girl ethos. “I personally wanted to work with Lola for a long time,” says Magee. “I would see her on Instagram a lot and would see the stuff she would wear. It is really close to a MadeMe vibe. She’d wear an old Polo Sport or an old Tommy Hilfiger piece.” In the images, Leon poses in fist-size hoops with straight, inky black hair—a natural, brooding fit...