Rosie met Daron Pope while he was working for Lehman Brothers. Her father-in-law, Mike Pope, is a coach for the New York Giants. Rosie and Daron's son, James Roderick "J.R." Pope, was born in September 2008, on the same day her flagship store in New York opened. Rosie struggled to get pregnant with her second child, Wellington "Wells" Reade, born February 5, 2011. She underwent in vitro fertilization treatments and had one of her fallopian tubes removed in the process. Six months after having Wellington, Rosie received news from her doctor that she was pregnant again. On May 13, 2012, Vivienne Madison Pope was born.