Chuck Taylor's. If I had to define America by a shoe, Converse Chuck Taylor All Stars would easily be that shoe. No other shoe has ever been so diverse, you can find them on senior citizens, break dancers, hipsters, young people, old people, geeks, elitists, teachers, punk rockers, jocks, and everyone in between. They come in a massive variety of colors and patterns to suit anybody's style, from laid back professional to grungy rocker.
Adidas Superstars are classic. Keep them white and clean and there is nothing you cannot wear them with. Everyone from John Cusack to Lil BowWow can be seen sporting these and that's no surprise considering its universally iconic and minimalistic style.
Puma Suede like the other shoes that made my list are incredibly diverse. All these shoes have been around the block more than a few times and still held there own and I have have every reason to think that these shoes will never go out of style. Fads may come and go, but these shoes are timeless.