A contemporary take on a 35-year-old design, the Frank Clegg Leatherworks signature duffel (frankcleggleatherworks.com) is made of green python skin and features Cognac leather trim. It is priced at $2,750. Frank Clegg established his leather workshop in 1970 in Fall River, Mass., producing handmade men’s and women’s bags that would last for decades. His sons Ian and Andrew eventually joined the business and are raising the profile of the small atelier and updating some of its classic designs—but not completely overhauling them. “We believe if something is designed with a timeless and elegant aesthetic, it should work now and for the future,” says Ian, noting that his father still spends much of his time in the workshop.