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10 of 28 1990: Madonna's cone bra Rob Verhorst/Redferns Since it was described as a symbol for female empowerment, Madonnas infamous cone bra first debuted at a concert in Japan in 1990, following major backlash over her song Like A Prayer. In the years following, the Jean Paul Gaultier look has become the single most recognizable garment associated with the singer

Sure, they look killer anchoring 2023's wide-fitting trousers and baggy shorts, but they also retain the signature comfort that made them a hit in the first placea win-win for style-minded dudes who grow a little more conscious of their podiatric health with each passing Supreme campout

Fit : Fitted at the top and waist, flaring out at the skirt

See all the ways I like to pair with leopard print shoes, here