Walkman, right angled headphone jack adaptor, a few cassettes... batteries... and a visit from the Special Branch because you did an e-bay search for, "Ammo pouch."
What kind of walkman? For my panasonic rq-s60 an external hdd leather case is a tight yet working fit. All the cases from my aiwas have not degraded in any way. (got to love that p-leather vinyl material)
I also have two other solutions winging their way to me, to see how well they work. I'll keep everyone up to date.
Not bad. It can easily handle two tapes and probably a spare set of batteries below them... and in here is the Aiwa PX303, the PX557 (with battery extender) and the Sony WM-EX502. The battery compartment did make it protrude, but the flap still covered it nicely . Obviously, the right angle headphone jack as the phones would need to come out sideways. A good enough solution if you're going to hit play, hold the controls and just walk.
I'd like those but in leather and dark colour. Looks perfect for travelling. BTW: I live that SONY EX502; it's the same one I had while I was studying photography in the 90s.