10. The Indian Phase
To be fair, Madonna has flirted with Indian-inspired fashion throughout the course of her career, but it was at its most glam during her 1993 Girlie Show tour. The dominatrix boots really add a little somethin’ extra, don’t you think?
11. The Not-So-Little Black Dress
Perhaps Madonna’s simplest look to date, the black Dolce & Gabbana gown she wore to the 1997 Golden Globe awards is also one of her most elegant. She’d just given birth to her daughter Lourdes, and gee, did she look spectacular or what? Bonus: She won the Best Actress in a Musical or Comedy award for Evita that night, too!
12. The Japanese Phase
Crazy red kimono by Jean Paul Gaultier at the 1999 Grammy Awards? Check.
Up next: Couples outfits, the 2012 Super Bowl, and more!