“Fun is not chic,” says Leandra Medine Cohen, the fashion icon. “It’s not tight and put together. And so it doesn’t present as luxurious.” And yet, she’s sticking to her signature playfulness—sporting diamond toe rings, wearing two belts at once, and reimaging necklaces as tiaras: “I’ve never believed that [fun and luxury] have to be separate from the other.” Her “messiness” is right for a broader moment that Medine Cohen characterizes, perhaps surprisingly, as hopeful.