The Air Jordan XVI was designed to be a multi-purpose and multi-style sneaker. It was released in 2001, right before Michael Jordan would come back from his second retirement. So while it had to be a playable silhouette, it also had to reflect MJ’s newly refined style as an older man.

Wilson Smith and his team decided to include a shroud that would allow wearers to choose whether or not they wanted a quieter design or a performance-based, louder option.

Like many other hoopers, the XVI became a favorite of Ray Allen’s.

“Every time I see that shoe—the Bucks PE—I always think about the uniform,” Allen said, via Nike. ” I think about the time and place.  It’s just like music for me, when you think about where you were when you hear a song, you think about where you were when you first heard it. And that’s kind of how I think about it with the XVIs. With XVI, I just remember exactly where I was, and all these memories flood back from the games that I played in, to the players that I played with—that whole era.

“Most notably, the last time I wore the XVIs was my last year with Miami. When I came into the locker room and everybody saw me with them on, they just…everybody put in their orders.  Everybody was like, ‘I’ve got to get a pair.’ And then I had the green XVIs that I wore for Christmas. Once everybody saw those, they went crazy.”

The XVIs drop on December 22, for $250.

Read more about Ray’s love of Jordans in our exclusive first-person essay. Photos courtesy of Nike