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Unmatched pieces can look as finished as a suit—like this silk wool floral shell and skirt (Michael Kors, $995 and $950) and swing coat (Rebecca Taylor, $520). The Kelly-esque bag (Tod's) is less structured than the original. January loves vintage but avoids '60s styles because "people will think it's silly, like I'm very Method, staying in character in outfits from work!"
Bracelet, Diane von Furstenberg by H.Stern. Shoes, Michael Kors.