One thing that comes to mind remember having that was "Hackers" looking gear around that time was this industrial looking portable CD player that came in this hardshell plastic case with a strap. It totally had this 90s military cyberdeck look.
And yes, rollerbladed the city streets listening to it 😎
A bunch of technomancers in the fediverse. Keep it fairly clean please. This arcology is for all who wash up upon it's digital shore.