4. Air Jordan XI "Cool Grey"
Even at the age of 40, Mike was taking kids half his age to the hole with ease and of course draining shots off his patented fadeaway. Jordan broke out the Cool Greys as a member of the Washington Wizards at his second home, where he gave some of his most epic performances — Madison Square Garden. His Airness went off for 39 points, not bad for an old man. As for the shoes, the all-grey-everything style soon became a staple for Jordans.