I wear a PFD any time I'm in water I'm not entirely intimately familiar with, or any time I'm in a group, when it comes to boats (Eagle Scout, swim team, etc, and with a bit of extra float I am pretty secure in being able to get most folks to safety at need, or be able to take it off if I need to). Solo in a canoe or something I'll whip the vest on just in sketchy areas, but if I am on any kind of river I probably have a helmet on because I am deathly afraid of clocking myself rolling a kayak or spilling out of a canoe and onto a rock.
Don't wear a bike helmet though because road rash hurts enough I don't know if I'll want to wake up from one that bad LOL, I hate being mummy-wrapped for weeks at a time! :blushing: Always wear gloves though, because being able to catch myself on my hands mostly saves me from my bike path wrecks.