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On Location in the Hollywood Hills
January and Ann strike a pose high above Los Angeles, just outside the private house Adam and the team used on Day 2 of the shoot. "The photos were meant to look like when Life magazine used to photograph celebrities in their homes," Adam explains. And instead of the rigid undergarments and vintage clothing January wears on Mad Men, O went in search of comfort. This modern striped turtleneck (Vince, $85) and soft floral taffeta skirt (Jason Wu, $1300) are true to the era, look good on almost every shape—and you can breathe in them.