Prior to his second retirement, Michael Jordan released the Air Jordan XIV (14) in several color-ways in 1998 and 1999. Of those color-ways, an Air Jordan Original 14 (XIV) Low was featured in White, Obsidian and Columbia Blue in its 1999 release. This low cut model is definitely very sleek and stylish, the classic Columbia blue is very classy and traditional. It was released on August 4th, 1999 and retailed at $130.

The Air Jordan XIV (14) was released in 1998/1999. This was the very last Air Jordan model that Michael would sport in NBA before his retirement; the only time he wore this model was during Game 6 of the 1998 NBA Finals, a.k.a. "The Last Shot" game. On January 13, 1999, Michael announced his retirement from the NBA basketball for the second time. Retired in style, the design was inspired by Michael's car, the Ferrari 550 M, and was made by Tinker Hatfield together with Mark Smith. This was the first Air Jordan that would feature laces with metal tips. Something that both the Air Jordan 15's and Air Jordan 14's designs also would use. The XIV's also began the trend of having a number of things that would count towards the model number of the shoe. On the XIV's each shoe had seven Jumpmen, the one on the side of the shoe on a Ferrari-like shield. They could be found on the insole, sole, back, side, 2 x lacetip and front. Counting them on both shoes makes it a total of 14 Jumpmen.