I was a broadcast and recording engineer as undergraduate and graduate school. Now commercial/instrument rated pilot. Probably 500K miles on commercial airlines, too. I have worn a lot of headsets. Things learned:
Over-ear cups don't seal well unless the clamping force is very high = uncomfortable. ANR over-ear headsets compromise this by reduced clamping force and counting on the ANR to bail them out.
ANR works best at low frequencies -- below the range of speech. This works fairly well in light piston airplanes because the engine puts a lot of low-frequencies into the cockpit. ANR sets do do very little in the higher speech/music frequencies.
Bose is a fantastically successful marketing company. They could slap the brand name on ordinary laundry soap and successfully sell it at double the average laundry soap price.
In-ear headsets have the highest performance, weight almost nothing, and take essentially no space for storage. Some people, however, say that they cannot stand to have "something in my ears." So, YMMV
Here is the headset I wear:
https://www.clarityaloft.com/products/the-classic-aviation-headset It is fantastic. The "Comply" foam tips seal out sound, beating the ANR systems. The transmissions from Air Traffic Control are the clearest of any headset I have tried.
When flying commercial I listen to my cell phone music using a "music" headset made by the same hearing aid company that makes the Comply tips. The sealing is so good that I don't hear cabin announcements and can't have a conversation with a flight attendant without pulling the tip out of one ear. (My wife taps me on the shoulder if the PA announcement is saying something important.)
Unfortunately these music headsets are no longer available.
The Comply tips, however are now being marketed to independent headset makers. Look here:
https://www.complyfoam.com/professional-products/ and
https://www.complyfoam.com/products/t-series/#
@omni550, I would suggest that you sleuth out and buy some earphones that are compatible with the Comply tips, ideally the professional model tips, and buy them. IMO this is the best solution, assuming you are not one of the people who cannot use in-ear and is thus doomed to the head-clampers.