Alexandra Wentworth in O Magazine

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Grecian Turn
While Wentworth's go-to evening wear is most often a long black sheath (suitable for life in conservative Washington, D.C., where she lived for the past seven years), she felt the pull of one of this season's seriously short—and beautifully draped—jersey minidresses (Derek Lam, $1,490). "I'd wear one every single day if I could be airbrushed in life," she says.

Bracelet, Rosena Sammi. Necklace, Shourouk. Heels, Proenza Schouler