Jul 6, 2023

Why we’re fascinated: Because Cupo can get away with being both a fierce cultural critic and head designer of the fashion brand Hood By Air, which he cofounded. Cupo, whose custom looks include designs for Michael Jackson, Lady Gaga, Britney Spears and RuPaul, got us through lockdown with daily episodes of “NOT REALLY,” his (now-defunct) podcast with friend Patrik Sandberg. He told The Cut, “We always do a wig” at HBA runway shows, underlining his Warhol-meets-downtown unorthodox aesthetic.

— Joshua Encinias