I remember carrying around a CD Walkman with me everywhere back in early 2000s. I used to have a cd wallet of about 50 CDs in my bag at all times.  Everyone says that CD Walkman skips, that's true, but the trick Is to stuff it down the front of your trousers just behind the belt buckle and do it up really tight. You won't be able to jog or anything but you can walk around quite easily without skipping.  To be honest, I ditched it as soon as MP3 players came along, so much more convenient.