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
Best of breed : Master & Dynamic ....,. take your choiice, on-ear, over-ear, or in-ear monitors ( it's a personal comfort choice) 

go the website and check out the links to the bevy of "best" reviews 

I have the MH-30s with the AQ Dragonfly . It bests my other pair of Beyerdynamic T51i's, that are fine units in their own right.

Sir Paul McCartney apparently bought a boatload of MDs for himself, his band,  and full  entourage.

https://www.masterdynamic.com/?gclid=EAIaIQobChMIis-NmLyl2QIVCI1pCh2CtgzYEAAYASAAEgJezvD_BwE


Rather than go for active noise cancelling headphones (all of which mess up the sound to some degree) why not go for in ear monitor type headphones (the type which stick into your ear canal and significantly block out outside noise)

Assuming you can live with this design (some folks hate them) there are loads of different options available at all sorts of price points. I use Shure SE535 which work great on my long haul flights and can definitely appreciate the quality of this set over some of my cheaper alternatives. There are lots of different suppliers and you can find a range of options that fit your budget here
https://www.innerfidelity.com/content/innerfidelitys-wall-fame-earphones

If you do prefer to go with active noise cancelling give the folks at Echo Audio in PDX a call, they take the time to find the best at different price points and I bought a pair of Sennheisers from them for my wife (who does not like in ear) which she finds work well
The best IEM is the Shure SE846. It is better than anything else for your application. Forget about cancellation nonsense and enjoy 37dB noise reduction with the memory phone buds.