Roger Sterling and Don Draper
When they aren’t smoking, drinking, or having affairs (three things they do a lot of), Roger Sterling (John Slattery, left) and Don Draper (John Hamm, right) are two of the partners running a prestigious New York City ad agency in the ’60s. Maybe you wish you were born in a different time, and working for womanizing, scotch-swilling ad men appeals to you. Maybe it doesn’t. Either way, those old-school suits are pretty nice.