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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

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To research this article, I collected 18 candidates dress shirts from top brands, plus the ones I already owned to compare side-by-side, in person

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