What Happens When You Get So Influential That You’re Bored by Your Own Aesthetic?

Looking for Purpose

Ms. Calderone grew up in a small town on Long Island, where, she said, her worldview, was fairly limited. “We didn’t travel,” she said. “We didn’t eat anything other than our Italian American pasta-and-meatballs kind of situation.” As the daughter of two hairdressers, she was enamored with the business of beauty. “I grew up going to my dad’s salon, feeling like daddy’s little princess,” she said. She described her mother as the kind of woman who “wouldn’t even go to 7-Eleven without lipstick on.”

She was artistically ambitious but struggled with follow-through, enrolling and dropping out of two colleges, before moving to Manhattan, where she shaved her head and got a job tending bar at a nightclub, the Tunnel. There, she met Mr. Calderone, who at the time was living in the basement of his childhood home in the Bensonhurst section of Brooklyn. She moved in, and they shared a Murphy bed.

When Mr. Calderone’s career blew up, Ms. Calderone served, at first, as his manager, and then as his travel companion. “There was this whirlwind of excitement and newness,” she said, as her world expanded to include A-list parties and European fashion shows. In 1998, the Calderones were among the earliest pre-construction buyers in the Clocktower Condominium in Dumbo neighborhood of Brooklyn. “It was the quintessential loft: big columns and beams, crazy views of the skyline and water,” Ms. Calderone said.

She and her husband spent Sept. 11, 2001, in their neighbors’ apartment down the hall, where the two couples sat together, stunned, as they watched Twin Towers fall. The neighbors reacted by moving out of New York. The Calderones reacted by resolving to have a baby. They bought the neighbors’ apartment, moved in, and welcomed their son, Jivan.

“Dumbo was isolating,” Ms. Calderone said. She had become a mother at 28, a younger age than many of her peers in New York, and while her husband’s career took off, she struggled with a sense of purpose.