Year: 1985
Sneaker: Nike Air Jordan 1

The NBA uniform code should have been perfectly clear: If a team is wearing white-based shoes, everyone on said team must follow suit. Nike had to know this when they produced the initial Air Jordan in red and black despite the Bulls' wearing white shoes-and maybe they did. The NBA fined Jordan each time he wore the new sneakers, and Nike responded with one of the most memorable ad campaigns in sneaker history. They also sold millions of dollars worth of Air Jordans, which should have covered the fines.