Better "Noise Cancelling" Headphones for Air Travel?


Full disclosure, I know next to nothing about headphones. I own a few pairs of ear buds and a pair of Bose noise-cancelling headphones for air travel and cutting the lawn. However, I have an upcoming international trip with my wife that seems a great excuse/opportunity to upgrade to a decent set of headphones. My wife won't care if she get the new set or the old, we can't both use the one pair, and it's a long flight.

For the trip, I'll be pairing my headphones with an iPhone/iPad & Dragonfly Red DAC that I already own. Budget is flexible but I'd don't want to go crazy...I'll probably spend <$500 but don't mind if people discuss other options within shouting distance of that amount to generate conversation.

My questions are:
1) How well do passive noise cancelling audiophile quality headphones cancel out the constant drone of a jet engine?..specific recommendations for those that would do it well, if any, appreciated

2) With that much background noise, are higher quality headphones even worth it or would I only notice the benefit in a quiet environment?..I'll probably stick to sharing my music with the family when in my own home so these aren't going to get tons of use outside of traveling.

3) Any recommendations for a pair of active noise cancelling headphones that sound better than Bose (QC35s) with the active noise-cancelling feature engaged?

Thanks in advance!
ethos123
Glad I asked. In my naivity, I had presumed that bigger over-ear style headphones would have more material to block out the sound and do a better job for me. Clearly, thats not the case and the IEMs are also going to take up a lot less room in a carry-on. Thanks guys.

I'll read up on the Master & Dynamic in-ear & the Shure.
let me help you on this, i spent a good time finding my own bose wireless speakers, they are the best, you read these two guides about wireless portables speakers i hope these guides will help you.
1. https://www.pollowers.com/best-wireless-speakers/
2. https://www.digitaltrends.com/home-theater/best-bluetooth-speakers/

please dont hesitate me to ask any question about them, i work in a media studio. thanks
I fly over 100,000 miles a year and can't wear over-ear phones because they press down on the sides of my glasses and hurt my ears if I wear them too long. After trying multiple offerings I settled on Beoplay H8  on-ear phones (https://www.amazon.com/Bang-Olufsen-Headphone-Cancelling-Bluetooth/dp/B00R45Z2IE) which do a resonable job of noise cancelling but are a huge improvement on Bose for sheer musicality.
My local dealer (HiDef Lifestyle) also said to look at Fiil Canvas if you need a cheaper alternative ( https://www.amazon.com/dp/B01M3X19TY/?coliid=I3LACQM8CHTZP&colid=26RXMWYWRALYX&psc=0&ref...)
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