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1 Madonna in Jean Paul Gaultier, 1991 Dave Hogan On her Blond Ambition tour in the 90s, Madonna would shed her pinstripe suit to reveal her Jean Paul Gaultier cone bra while performing Express Yourself. When she went to Cannes in 1991 to promote Madonna: Truth or Dare , which documented the controversial tour, she re-created the moment in a sea of black tuxedos and adoring fans

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A micro-mini dress with a flared skirt and long, wide trumpet sleeves, it was usually worn with patterned tights, and was often made of crocheted lace, velvet, chiffon or sometimes cotton with a psychedelic print

Some shades leading the season include: Classic neutrals: A black fall midi dress is timeless, while a white fall midi dress works beautifully when styled with boots and a trench coat