Ashley Olsen

Kevin Mazur, WireImage | Stephen Lovekin/Getty Images

Uptown: CFDA Fashion Awards 2011
Look: Bold brows, tousled hair, and smoky eyes keep the actress and designer's look cool, yet chic.

Downtown: "Midnight in Paris" Screening
Look: Olsen pairs her '60s-inspired polka dot dress with a soft updo, piecey lashes, and touch of lip gloss.