We thank designers like Yves Saint Laurent whose trailblazing ‘Le Smoking’ tuxedo for women blurred the gender lines of fashion. The days of pant-clad ladies causing scandal all around town in for-men-only pieces are long gone. But lately, we think there is something shocking about how great a pair of menswear-inspired shoes are looking.

We love little touches of men’s detailing—think monk straps and kiltie fringe—and reinterpreted classics like loafers, boots and oxfords. Try starting with a look that’s tailored and feminine, and add this trend for a touch of boyish charm.
Shop menswear-inspired women’s shoes.
Main image (clockwise): DV by Dolce Vita ‘Wyatt’ Bootie, Steve Madden ‘Cablee’ Boot, Seychelles ‘Clue’ Bootie, Trouvé ‘Curtis’ Slip-on
Right column: Yves Saint Laurent ‘Tribute’ Platform Slingback, Børn ‘Arletta’ Oxford, Ralph Lauren Collection ‘Nadine’ Ankle Boot






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