Jenny Cipoletti has built a world all her own—one shaped by romance, nostalgia, and an abiding love of beautiful things. The founder and creative director describes her style in three words: Collected, Feminine, Enduring. A lifelong lover of vintage, she looks to the mid-1960s for inspiration: "I'm drawn to the clean lines, playful femininity, and sense of freedom that defined the decade," she says. "There's a timelessness to the silhouettes and styling that still feels fresh today."

Her closet is filled with pieces chosen not because they follow trends, but because they tell a story. "We all who love vintage crave this sense of nostalgia," Jenny says. Whether it's a Viennese couture ensemble she never quite got around to tailoring, a Miu Miu skirt that reminds her of nights out after fashion week, or a pair of earrings discovered in Florence and "snagged up so quick," each piece carries a memory and a sense of possibility. Above all, Jenny is drawn to clothes that make room for whimsy. "There's an element of playful whimsy that I like to incorporate into the way that I dress," she says—a sentiment woven throughout this edit and ready to be carried on by someone new.