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Who: Anna Cleveland.

When: Thursday, June 16.

Where: The premiere of Orange Is the New Black Season 4 in New York.

What: A Spring 2016 body suit by Roberto Cavalli paired with a Just Cavalli tuxedo jacket.

Why: Cleveland consistently proves she can pull off quite severe looks, and this Cavalli ensemble is no exception. The skin-tight outfit, paired with a sleek, center-parted ’do, embraces two of this season's favorite trends — the menswear-inspired look (that tuxedo jacket!) and the jumpsuit-as-formalwear. At a moment when more and more designers are collapsing their men's and women's collections, it couldn't be more appropriate.