Year: 1987
Sneaker: Nike Air Jordan II

In 1987, Nike as a company was just 15 years old. And just a few years before that, they were a company in trouble, saved by a 6-6 guard from North Carolina. So when it came time to do Michael Jordan's second signature shoe, they could have played it safe. A few changes here and there, make the ball and wings logo more prominent, raise the price a bit and call it good. But no. Instead, they released a sleek, Italian-made sneaker with a polyurethane sole, faux lizard skin trim and-shockingly-no Swoosh at all. For $100. In this case, the bold move was the right one, as the following shoe (also Swooshless) took Air Jordan to new heights.