You have to remember too that this was a sort of transitional phase of hip hop fashion. This was the era when Big, Jay, and Nas were bringing in that Versace style stuff. This was jumping off the "jiggy" era and dudes hadn't yet found their lane.
Personally, I also think this was one of the wacker fashion eras in hip hop history.
Basically, the distance between the fashion culture and "the people" is usually pretty closely related to the distance between the music itself and "the people."
When rappers were rocking fatigues and Timbs, their music was relate able to young people in any hood out there living the hip hop lifestyle. So was their fashion - rappers looked like their fans. As it evolved into pure decadence, the music went further away from the people too - I can't relate to pouring champagne on women on a yacht, or shopping at the Bentley dealership. The jersey era brought something of a return to the streets. The rappers looked like their fans again. Now, this couture stuff reflects the same trendiness and style-chasing, lack of core identity that pervades the music scene. ...We've seen this type of relationship throughout the history of the music, as the dookie rope gave way to the Africa medallion.