Nobody has ever mistaken the fashion world for a welcoming, kind place, and every neophyte, at least when I was starting out, was subject to a scrutiny so unsettling that it bordered on hazing. The elders of the tribe—for me, Horst, Geoffrey Beene, Grace Mirabella, Eleanor Lambert—were not the problem. They adored refreshing themselves with young blood, the better to stay au courant.

Roberts, center, with Graydon Carter and Amy Fine Collins at a Ralph Lauren Collection show during New York Fashion Week in 2010.

By far the toughest cohort to conquer was the group half a generation ahead of me, which then consisted of a formidable lineup of characters including Marina Schiano, Eric Boman, André Leon Talley, and Michael Roberts.