Looking for ANC headphones for listening to audio dramas

Hi all! I currently have the Shokz OpenDots One and I love them for music and talking on the phone. I've been listening to more audio dramas lately (currently listening to The Magnus Archives), and it's hard to hear all the detail of the audio engineering with these headphones, especially in specific settings. The three most important things for me with this new pair are ANC, comfort, and it will last me several years.

• Budget and location - Ideally, I'd like to spend around $100, but I can go up to $250 if needed (including shipping and tax). I have some gift card money on Amazon, but there's a Best Buy near me that I like to visit to try headphones on in person.
• Preferred tonal balance - Honestly, I'm not sure yet! I do like having the ability to change the EQ mode to a preset (the Shokz app lets me do that). An old pair of headphones I had (Skullcandy Crusher Evo) had presets for music vs calls vs podcasts, etc. which was nice too
• How the gear will be used
  • These will mostly be used on walks during the day (I live in Southern California so IPX5+ would be a nice to have but not needed)
  • Indoors between the laundry room and my apartment
  • Air travel
  • Temporarily be used for occasional meetings while I figure out the crackling/popping issue between my Shokz and my desktop with Shokz support (my Shokz work with literally all other devices) but overall, I don't need a fancy mic; just something good enough to use if someone happens to call me while I'm wearing them.
• Past gear experience - I've used both over-ear headphones and earbuds, and have had comfort issues with both. I find my current pair, which just clips to the outside of my ear, the most comfortable I've worn. I sometimes forget I'm wearing headphones even if I have something playing.
  • I used my Skullcandy Crusher Evo everyday for 2 years before they died, but I found these would get uncomfortable after wearing them for about 2 hours.
  • I used to have Samsung Galaxy Buds 2, but they also died after a year or two and my ears felt sore after wearing them.
  • I also used to have Apple Airpods and had the same issue; they died quickly and my ears felt sore after wearing them for a certain amount of time.
  • I also used to have a pair of Turtle Beach headphones for my Xbox that I absolutely loved (great quality, amazing features, easy to connect), but they were tight on all sides of my head, so it was hard to wear them for long periods of time.
  • I tried the Sony WH-1000XM6 at an audio store at the airport once and those were probably the only over-ear headphones I found comfortable. Of course, I also loved the audio quality buuuut that price tag hurts

I feel like I've gone through a decent amount of headphones in no time, which is why I want my next pair to last me a while. I know I typed out a lot, hopefully I made it easy to go through, but definitely ask questions if you need me to clarify anything. Thank you in advance! I appreciate any help you can provide.