Courtney Crawford grew up in a household with five women, and apparently their love of shoes was contagious. In the Spring of 2006, he launched his debut collection of footwear and has since collaborated with fashion houses like Missoni. It’s difficult to pick one shoe that’s prettier than the rest, but oh how we love the architectural details of his patent leather peep toe. It’s fun to wear with a black jersey knit dress. Accent your assets with red (think lips and nails).

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