42. Nike Air Pegasus 92
Which Pegasus warrants a position here? Most of them up to 1992 are fantastic. The 1983 original, Pegasus Plus, Pegasus GX, the Pegasus ACG, the 1988 version (marginally better than the 1989 take that got retroed), the 1990 version with the heel lettering and the forgotten Pegasus Racer are classics, but the 1992 variation in concord blue, maize and white is the ultimate entry. After this, the formula got stuck in repeat before the shoes became progressively more ugly until they got pretty again in late 2008. This model's plastic heel application and teched-out sole unit is a thing of beauty. Whether they were black-on-black or kept light, it seemed the line peaked right here. Other shoes from the era like the Air Base IIs were cool, but the cheaper Icarus line of lightweight running couldn't come close to their similarly mythically monikered siblings.