OP,
For that money, Audio Technica makes some mean Bluetooth headphones. If your friend doesn’t have/doesn’t want an amp/cd player/DAC etc. and listens to music with a smartphone/laptop, then Bluetooth would be the best option.
Another option could be the Sony WH-1000XM4 noise-cancelling headphones. They sound very good and balanced; unlike many of the celebrity headphones lurking out there.
How comfortable a headphone wears is a personal thing. Over-ear headphones would be more comfortable than on or in-ear monitors.
For that money, Audio Technica makes some mean Bluetooth headphones. If your friend doesn’t have/doesn’t want an amp/cd player/DAC etc. and listens to music with a smartphone/laptop, then Bluetooth would be the best option.
Another option could be the Sony WH-1000XM4 noise-cancelling headphones. They sound very good and balanced; unlike many of the celebrity headphones lurking out there.
How comfortable a headphone wears is a personal thing. Over-ear headphones would be more comfortable than on or in-ear monitors.