New York Magazine editor Jenny Kang proves you can wear a menswear-inspired piece in a very feminine way. Her metallic Alexander Wang oxfords sport tassels and a heel, and are the perfect accent to a blazer/dress combo.
Katy Perry goes full-on pop diva with electric blue oxford shoes, a thin-lapel blazer and a fedora. The reason it works: She keeps her outfit neutral so her red lip and statement shoes can stand out.