Nat Sherman

While the Native American statue outside and neon “cigars” sign inside this midtown townhouse are eye-catching, the rest of the atmosphere in this family-run, 86-year-old shop is of a different time—one where you could legally enjoy a smoke in your suit after business hours (or during lunch). It offers an affordable variety of brands (from $5 to $50), such as the mellow, medium-bodied Sterling Selection, as well as hand-rolled cigarettes that will put those bodega smokes to shame.