Caroline Vreeland

Vreeland wears Max Mara coat; The Row sweater; Tabitha Simmons booties.

Photographer: Ami Sioux
Stylist: Jessica De Ruiter

“In my early 20s, I really wanted to be seen for who I was, and not this blonde girl with big boobs and a family legacy,” says the musician Caroline Vreeland, the great-granddaughter of the fashion editor Diana Vreeland. Now 27 and all the wiser, Caroline, who only met Diana once, when she was a toddler, has come to embrace her famous surname. “I’m lucky to have that as part of my story,” she concedes.

A native of California’s Bay Area, Vreeland moved to Los Angeles at 18 to be a singer-songwriter. After releasing three moody tracks online in 2014—and performing at afterparties for Vionnet and Barbara Bui during the fall 2015 shows—she dropped an EP, Glasshouse; she will debut a full-length album in October. Describing her sound as “doomed magic,” Vreeland has found a kinship with her great-grandmother through her work. “She stood for being yourself and embracing your flaws, making them what’s sexy and interesting about you,” Vreeland says. “My music is an expression of everything that makes me me—not just the pretty parts.”

Hair by Caile Noble for Serge Normant at Jed Root; Makeup by Debra Ferullo for LancOme at Tracey Mattingly. Photography assistant: Adam Torgerson. Fashion assistant: Fiona Park.