Madonna's 57 Iconic Fashion Moments Ahead of Confessions II

Madonna is set to release her new album Confessions II, the follow-up to 2005's Confessions on a Dance Floor, marking her first new album in over a decade. To celebrate, a retrospective highlights 57 of her most iconic fashion moments over 40 years. Her career began in 1983 with hits like "Holiday" and "Lucky Star," instantly making her a global trendsetter with tulle skirts and lace gloves. Key looks include the Jean Paul Gaultier cone bra from the 1990 Blonde Ambition tour, a Givenchy floral headpiece at the 1996 Evita premiere, and a gold-and-black ensemble by Riccardo Tisci and Philip Treacy for the 2012 Super Bowl halftime show. At the 2021 VMAs, she wore a leather dominatrix bodysuit. For her 2023 Celebration World Tour, she wore custom pieces by Jean Paul Gaultier, Versace, and Dilara Findikoglu. In 2026, she performed in Times Square in a vintage Gucci jacket. Recent homages include Sabrina Carpenter wearing a vintage Bob Mackie dress at the 2024 VMAs, originally worn by Madonna at the 1991 Oscars, and Dolce & Gabbana's spring 2025 show featuring Madonna-inspired looks.