Madison Avenue, here I come!
Ensemble 1: 2009's tweedy working girl outfit, inspired by classic Ms. Holloway style.
Skirt: Graeme Black / Blouse: Marciano / Earrings: Gurhan / Ring: David Yurman / Handbag: Nancy Gonzalez / Shoes: Paris Hilton
Ensemble 2: An uber-modernized take on Ms. Holloway's blue moment.
Dress: Freda / Belt: Oscar de la Renta / Earrings: Roberto Coin / Bracelets: John Hardy / Handbag: Cole Haan / Shoes: Steve by Steve Madden
Ensemble 3: A chic, contemporary version of Ms. Holloway's fierce magenta sheath.
Dress: DVF / Ring: Kate Spade / Necklace: Cara Accessories / Bag: Prada / Shoes: Charles David






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