I still have a Sony Walkman Professional WM-D6. I bought it to transfer old cassettes of studio recordings a few years ago but i have been unable to get rid of it. It sits alone on a shelf, fully boxed with all of its accessories including the remote and will probably be placed on Ebay by one of my chilfren in a couple of decades time. I'm sure it will still work as perfectly then as it does now.

I have three Sony Walkman's, although they are quite a bit more bulky then the present day equipment, I find they are very convenient for changing over various audio tapes from music to instructional passages, and I can adjust the volume to any level without bothering anybody. And yes, I do use them quite a few times every week!

Before the Walkman there was Astraltunes out of Reno Nevada in 1975.

Vinyl, then tape, then mini disc, then cd, then thumb drive. Computers, chips and salsa. I keep my cassette players. Unless I was on fire and the only way I could put myself out, was to play something audio on the old tape format: I'd still think about it twice. Since moving to digital, my impatience level with anything audio/video, especially the tape format, increased exponentially. I have pure platinum recordings that will never see the light of day.

actually the belts will be useless in about 10 years after being made... rubber parts decay
wle

I was a proud owner myself. I had a neoprene waist belt for it plus a 4 band inline equalizer. My headphones were sony also, they clipped behind the ear. Fun memories.

Still own my Walkman and cassettes. Used it when Alpine skiing mostly but did buy a carrying case which had two speakers (3" x 3" x 6" each) which was sort of a boom box. Like to part with it but with todays tech, I'm afraid it would end up in a land fill.

I had an M-80 microcassette at uni. In my yearbook my classmates said it was my life support system. It could record as well as play back and had AM/FM radio. I used to walk around listening to Radio 2 (UK) and recording it simultaneously. You could even drop the speed to half for extended cassette life... and it had a loudspeaker. Truly a design classic!
https://www.youtube.com/watch?v=0PlqiytIF_0

"WLE" Yes most belts decay, my 35 year old dual cassette deck belts dried out and don't turn. However the tape deck on my 17 year old van still work, haven't tried the CD player recently.