36. New Balance 991

Year: 1999

If the New Balance 991 is good enough for Steve Jobs, it's good enough for you. 1998's M990 was a good shoe, but the 1999 incarnation was an expensive dose of ABZORB, beneficial details for the mild pronators, all-terrain styling and a bulk that's like little we'd seen before. This isn't a shoe that panders to fashion, but in neutral colors it's a modern classic that's well-made, unique and a constant bestseller globally, with the horde of European disciples to this, the 992 and the 993 growing by the day.