The Hottest Boots of the Season

Riding boot

For a classic look, Adam says a riding boot is a great go-to—especially in gray. "Everyone likes a riding boot," he says. "Gray is very big. It's big in boots and big in clothing."

Have trouble finding boots to fit your calves? Adam has the perfect option for you. "These are extra-wide boots from J.Crew—the best boots out there for a wider calf," he says.

Boots: J. Crew Nottingham boots in gray, JCrew.com; dress: Calvin Klein, Macy's; sweater: International Connection, Macy's; purse: Fendi Peekaboo bag, NeimanMarcus.com

Adam Glassman's Boot Bible:

• Best boots for under $100
• 17 great ankle boots