The shoemakers Trafton Cole, William Rood, and Edward Haan opened shop in 1928 to bring style and polish to Chicago gents with their high-quality, handcrafted footwear. Cole Haan pays homage to the Jazz Age silhouettes of its founding cobblers with Cole, Rood & Haan, a capsule collection for men featuring dressy loafers ($325), refined work boots ($395), and natty ankle skimmers ($350). Popped collar and tony swagger not included. Available exclusively at Cole Haan (673 N. Michigan Ave.; colehaan.com).

Photograph: Courtesy of vendor