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KRAZY Pointed Boot, $60, Topshop 39

Consider the garment an LBD with a twist

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

Sizes: 2-4 Colors: Silver Complete in a print that dresses up the always-reliable slip dressand with a knee-high slitthis dress perfectly transitions from wedding to brunch in the peak of autumn

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