Michelle Obama

Not only was Michelle on Vanity Fair's International Best Dressed list this year, she has been wearing an interesting mix of designers like Isabel Toledo, Tom Binns, and White House Black Market — she is playing the fashion field. This Summer she attended a fund-raiser in her honor in New York where fashion folks Zac Posen, Iman, Tory Burch, Catherine Malandrino, and many more sang praise to the potential First Lady. But this Thakoon Resort printed sheath is stellar; it's unique, festive, and professional. Her minimal jewelry is a must with such a stand-alone dress and her black patent flats have Jackie O written all over them.