As for style, the “cool girl” in her oversize blazer and baseball cap, with her quiet luxury dreams and her pricey smoothies, has been so popular for so long that she’s starting to seem like a menace.

Think Massimo Dutti, Zara, and Jeffrey Campbell mixed in with Gucci, Prada, and Celine. What each of these shoes shares is a '90s look with a twinge of old Prada—the latter is more noticeable in ...