22. Saucony Jazz
You might think the Saucony Jazz looks basic now, but long before it became one of the hardcore scene's shoes of choice this was a pioneering runner. Made with podiatrist Dr. Frank Santopietro as consultant, the Maxitrac outsole, emphasis on balance, sock insert, narrow heel and more substantial forefoot all combined on this bestseller that spawned the Jazz series. Total performance and a softer feel than the harder soles of previous years, plus a simple look that's ultra versatile makes this iconic. The Shadow series also deserves a shout here.