The Sennheiser Accentum Wireless sit slap bang in the middle at around £160 / $180 / AU$300 at launch, as do the Sony ULT ... sensitive system. They're reasonably comfy, too. The P100s' earcup pads ...
The Sony Walkman was a cultural revolution, enabling people to play any song, anywhere, anytime --- long before similar freedom existed for movies, e-books, or video games.