I wear mine when I fly, but I also fly with gloves so I feel like that mitigates the risk. I'm also not a guy that pops the mask off after fence out/prior to fence in FWIW
It doesn't. Sorry man, growing up on a farm, in a farming community, I know too many people missing left-hand ring fingers. Gloves do not prevent you from losing it when your full body weight comes down on it. It will still absolutely hook the side of the cockpit, or whatever, through the glove, and take your finger off.
I still fly with my ring on, and I wear gloves too...but I just accept the risk and move on. I justify it to myself this way: At least I'm wearing gloves (fingertips intact and all).