Adam says the over-the-knee boot is the hottest style of the season. "It's back. Remember we had these in the '80s?" he says. "You want to wear a flat one because if you wear a heel one it's a little too Pretty Woman."

Adam says to match the color of the boot to your tights, leggings or pants. "They can make your legs look longer and leaner if you dress tonally," he says.

Boots: See by Chloé, Zappos.com; coat: Theory, Macy's; leggings: BCBG, Macy's; purse: Chanel, NeimanMarcus.com