Summer School

What Mad Men's Sally Draper might wear her senior year: scholarly oxford collars, checkered skirts, and high-heeled loafers with attitude aplenty.

June 13, 2012 11:00 AM

Head of the Class

Jacket, $998, Rachel Roy; top, $720, skirt, $940, J.W. Anderson; socks, $12, Kate Spade; shoes, $895, Rochas; bag, $940, Marni; sunglasses, $340, Oliver Peoples. On hair: TRESemmé 24 Hour Body Non-Aerosol Hair Spray.