Stephanie Ann Whited, 28
By day, Whited is the communications director for Schools That Can, an educational nonprofit; by night, she's working on publishing her first book of poems. "I write a lot about questioning the boundaries of self," she says. "I like experimenting with new things." Case in point: this suede miniskirt, shorter than Whited would normally wear but comfortably balanced by a long-sleeved oxford and cotton sweater.
Miniskirt, H&M, $99. Oxford, J.Crew, $78. Sweater, Rebecca Taylor, $295. Flats, Maloles.