Headphones were a solved problem. I had 20 years ago some high end IEM that i used back in the days on on so called mp3 players - those were pocket sized music players - and since apple released the airpods and bluetooth headphones were the new standard audio quality never recovered to the state we had two decades ago
iPod Shuffle + Shure SE215 was the pinnacle of portable audio. The ritual of maintaining a separate playlist that would actually fit made it intentional. Allowing Spotify to slip into an infinite stream of slop is so easy these days.