Year Released: 1984

Converse was never really a tennis brand, but in the late 1970's and early 1980's, any major athletic footwear brand that wasn’t in tennis was a mid-major. That's how much tennis mattered. As an original US brand, you really had two choices if you wanted to hire a tennis star. John McEnroe and Jimmy Connors. Chip Hooper, anyone? The Connors Classic released during the 1984 Olympics was awful. Really uninspired. But the original Jimmy Connors All-Star was a really interesting shoe. Very clean, vulcanized bottom and the heel counter featured an extra large Converse star cutout, backed with color (is navy a color or the absence of color?). Jimmy Connors was an animal. He made a major comeback in 1991 at age 39 and reached the semi-finals of the US Open (wearing Air Tech Challenge). To put that in perspective, Bjorn Borg retired at age 26. Andy Roddick just retired at age 30. Of course, Jimmy probably wasn't going home to Brooklyn Decker standing naked in the kitchen wearing heels and making a pot roast.