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
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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When I travel I can't deal with the bulk and pressure from over or on ear headphones as I get sinus troubles during travel on dry planes. For a while that meant no noise canceling for me, but now that may change. I am closely watching Bluetooth 5 specifically the new Qualcomm chipset. It's not widely available yet but once it is there will be some pretty advanced ANC included. More on that here: https://lonelybrand.com/blog/next-gen-wireless-devices/

In the mean time I go for cheaper earbuds that actually make a good seal in the ear, which does have a pretty substantial noise canceling effect when on the plane. There's a pretty good list on the same site as the guide I linked above here: https://lonelybrand.com/blog/next-gen-wireless-devices/
Any Shure IEM with the foam tips, properly applied, are the best,
You have to go through the ritual though. Squeeze the tips with your fingers, hold them in while pulling up on your ear. This ensures the best noise blocking and bass response.

They used to use yellow foam, which was much like you'd buy for construction work, but they are high maintenance. The black foam tips are about as good but last longer.