When Gavin Hoffman, a former UPenn quarterback, couldn't find the perfect pair of men's loafers, he resolved to make his own. He left a career in finance in 2009 to start work on Austen Heller, his take on the traditional driving moccasin in stylish colorways—rich leather with red soles, blue suede with orange stitching. The durable soles are designed for comfortable pavement-pounding, while the body is made from Italian leather and suede, all hand-stitched in Portugal.

Austen Heller kicks are available at Haberdash (607 N. State St.) and ZipFit Denim (both the Chicago and Skokie locations) and retail for $195. As a complimentary perk for Chicago residents, Hoffman also offers delivery service. Upon request, Hoffman or a member of his team will tote a variety of styles and sizes straight to your home or office. Now that’s service.