words // Luis Sanchez

For over two decades, the Jordan Brand has not only produced some of the most memorable sneakers, they’ve also consistently dropped some of the best casual sport-inspired men’s Jordan clothing. Taking the lead in our latest trip down memory lane, we see some of the most memorable apparel put out by the Jordan Brand way back in 1999.

From the popular velour suit to hoodies matching the Jordan XIV at the time, the Jordan brand was doing it big right before the new millennium. Another rare sight is the man himself, Michael Jordan appearing in the ads showcasing all of the latest Jordan Brand apparel. We also get a rare shot of MJ in a pair of the Air Jordan XIV Low, a shoe he originally only wore once in his final game as a member of the Chicago Bulls.

Continue below for a trip down memory lane courtesy of Eastbay and the Jordan Brand.