"This decision, per the NBA’s website, had an interesting side effect: Michael Jordan’s UNC short shorts wouldn’t fit under his Chicago Bulls short shorts, so he had to wear baggy, knee-length Bulls shorts instead, as seen here. In doing so, he broke the mold set forth by players before him. As proof, in the “It’s gotta be the shoes” ad, you’ll note that at the 0:13 mark, Mars Blackmon (played by Spike Lee) asks if the secret to MJ’s game “is the extra-long shorts.” Even then, the shorts were still considered a deviation from norms of proper basketball apparel.
Soon, these extra-long shorts became the favored style. By 2003, almost every single NBA player had jettisoned the short shorts for the longer variety (with future Hall of Famer John Stockton being a notable holdout). Looking back, it is clear that Jordan had a lot to do with this change in basketball fashion trends. In 1991, the University of Michigan’s Fab Five, featuring two future NBA All-Stars in Chris Webber and Juwan Howard, wore the same type of shorts as Jordan did—ESPN, in a documentary about these five Michigan freshman, featured their shorts on a promotional poster. And in that same documentary, the Fab Five explained why they wore the long shorts:
"But the real short-shorts stuck around until Jordan discovered he didn't have enough room to wear his University of North Carolina shorts underneath his Bulls shorts.
The legend about Jordan and the shorts is mostly true: In order to stay close to his alma mater, so to speak, he needed more space. So he approached Champion, then the NBA's apparel-maker and outfitter, through the Bulls and asked that his shorts be wider and longer. Plus, since Jordan tugged at his shorts when he tired, he risked pulling them down below his waist. Although, in a coincidental twist, this is the fashion rage today: teenagers wearing sagging pants which expose more than we're willing to see.
"It's just something that seemed more natural, more comfortable to me," Jordan said many years ago. "They felt great."
Jordan also appeared in several Nike commercials with Spike Lee wearing the roomy shorts. Jordan was emerging as an icon and trend-setter among kids both inside and outside city limits and the commercials caught on nationally. So did the shorts, albeit slowly, in the NBA.
For the 1989 season, Jordan was the only player with the specific-tailored shorts. Then his teammate, Scottie Pippen, requested a pair. That offseason, the idea caught fire.
"It was a league-requested change, based on feedback from the players," said Cathy Marchant, the senior marketing manager for Champion. "The equipment managers of each team requested new shorts."
The change was felt in college when UNLV went baggy, too. The Fab Five from Michigan took the idea a bit further, literally, when their shorts were worn at the kneecaps and flapped in the breeze when they jogged upcourt. Roomy shorts became street fashion, and cool was measured in inseam and rise inches. Other than when Stockton wore them, short-shorts have disappeared much like CDs and phone booths. Even women's teams began wearing long shorts."