Steven Meisel and Madonna, Sex, 1992

Madonna is one of pop culture’s greatest chameleons. The 1980s found her championing big hair, bows and berets before shifting to sexy Jean Paul Gaultier ensembles a decade later. Her 2001 Drowned World tour saw her embrace a DIY punk aesthetic while ten years on she was sporting sleek designer gowns. But most notable of all her stylistic reinventions were the looks she donned for her seminal 1992 book Sex, featuring photographs by Steven Meisel. The now-out-of-print publication is a riotous celebration of S&M, queer culture and all things sexual. It features the singer in everything from corsets to tailored menswear suits and Marilyn Monroe-channeling silk numbers. She challenges convention on every page, and looks fabulous doing so.