Cybill's classic look pairs a white shirt with timeless khaki cigarette pants.
Clementine pairs a modern white shirt with a 1950s-inspired skirt. "The skirt is navy and black, which is really okay to do," Adam says. "Everyone should know that you can mix navy and black and wear it together."
Ariel's look can take her from day to night with a sexy cargo pant. "Let me just say, the cargo pant is in lieu of the sweat pant," Adam says. "Get rid of your sweat pants and wear the cargo pant. You can dress it up and wear it out."
All pieces from Saks Fifth Avenue.
Sweater: Lafayette 148 New York; shirt: Ralph Lauren; pants: Piazza Sempione; shoes: Tory Burch
Shirt: Derek Lam; skirt: Naeem Khan; shoes: Sergio Rossi; bag: Marc Jacobs
Jacket: Smythe; shirt: Jil Sander; pants: Joe's 55; shoes: Jimmy Choo; scarf: Eileen Fisher